Ethyl (S)-1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate
- CAS Number:180468-42-2
- Molecular Formula:C18H19NO2
- Molecular Weight:281.354
- Mol File:180468-42-2.mol
Synonyms:2(1H)-Isoquinolinecarboxylicacid, 3,4-dihydro-1-phenyl-, ethyl ester, (S)-;2(1H)-Isoquinolinecarboxylicacid, 3,4-dihydro-1-phenyl-, ethyl ester, (1S)-;Ethyl (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate;
Physicochemical Properties
- Melting Point:N/A
- Boiling Point:412.2 °C at 760 mmHg
- Density:1.145 g/cm3
- Solubility:N/A
- Flash Point:203.1 °C
- Vapor Density:N/A
- Refractive Index:1.582
- Sensitive:N/A
- Storage Temp.:N/A
- Appearance/Colour:N/A
Ethyl (S)-1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate Safety information and MSDS
·Hazard identification:
Pictogram(s) | ![]() |
---|---|
Signal word | Warning |
Hazard statement(s) | H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation |
Precautionary statement(s) | |
Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. |
Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/…if you feel unwell. |
Storage | P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up. |
Disposal | P501 Dispose of contents/container to ... |
·Composition/information on ingredients:
Chemical name | Common names and synonyms | CAS number | EC number | Concentration |
---|---|---|---|---|
ethyl (1S)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate | ethyl (1S)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate | 180468-42-2 | none | 100% |
·First-aid measures:
General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
·Fire-fighting measures:
Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.
·Accidental release measures:
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.
Ethyl (S)-1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate Relevant articles
All total 23 Articles be found
Synthesis, potential anti-inflammatory and analgesic activities study of (S)-N-substituted-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxamides
Guan, Li-Ping,Xia, Ya-Nan,Jin, Qing-Hao,Liu, Bing-Yu,Wang, Si-Hong
, p. 3378 - 3381 (2017/07/07)
A series of (S)-N-substitued-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxamide derivatives were designed, synthesized and evaluated for their anti-inflammatory and analgesic effects in vivo. Among the synthesized compounds 2a and 2n showed the best anti-inflammatory activity (inhibition rate: 95% and 92.7%, respectively) and analgesic effect (inhibition rate: 100% and 100%, respectively), which was greater than that or nearly equivalent to that of indomethacin. Compounds 2a and 2n were selected to test their inhibitory effects against ovine COX-1 and COX-2 using the cyclooxygenase inhibition assay in vitro. Compounds 2a and 2n are weak inhibitors of COX-1 isozyme but displayed moderate COX-2 isozyme inhibitory effects (IC50?=?0.47?μM and 1.63?μM, respectively) and COX-2 selectivity indexes (SI?=?11.5 and 4.8). Furthermore, compound 2a was more inhibitors of COX-2 isozyme active than the reference drug celecoxib.
Study on synthesis and biological effects of a series of 3,4-dihydroisoquinoline-2(1H)-carboxamide derivatives
Fu, Zhi-Yang,Jin, Qing-Hao,Xia, Ya-Nan,Jiang, Hai-Ying,Guan, Li-Ping
, p. 52 - 61 (2018/11/30)
In this paper, we have reported the synthesis and biological evaluation of nineteen (S)-N-substituted-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxamide derivatives as novel candidate antidepressant and anticonvulsant agents. Compounds 2h, 2k, 2r, and 2s exhibited better potent antidepressant activity and displayed the antidepressant effects in a dose-dependent manner from 10 to 30 mg/kg in the FST and TST. And, we found that the best antidepressant effect of compounds 2r and 2s are likely mediated by an increase in central nervous system 5-HT and NE. In addition, compounds 2r and 2s also exhibited the anticonvulsant activity against MES-induced seizures. Thus, compounds 2r and 2s may be a useful antidepressant adjunct therapy for treating depression in patients with epilepsy. In addition, compounds 2r and 2s showed the anti-inflammatory activity and the excellent analgesic activity. Several scholars have postulated the anti-inflammatory and analgesic effects of antidepressant drugs, suggesting that they may be possess a similar mechanism of action.
Preparation method and application of solifenacin derivative
-
Paragraph 0015; 0016; 0019; 0022, (2018/09/08)
The invention relates to a preparation method of a solifenacin derivative. The preparation method includes the steps of: (a) using a solifenacin EP impurity A shown as formula 1, adding chlorine dioxide shown as formula 2 in the presence of potassium carb
Highly Enantioselective Arylation of N,N-Dimethylsulfamoyl-Protected Aldimines Using Simple Sulfur-Olefin Ligands: Access to Solifenacin and (S)-(+)-Cryptostyline II
Jiang, Tao,Chen, Wen-Wen,Xu, Ming-Hua
supporting information, p. 2138 - 2141 (2017/04/27)
With the use of a simple sulfur-olefin ligand, a highly enantioselective rhodium-catalyzed addition of arylboroxines to N,N-dimethylsulfamoyl-protected aldimines has been achieved, allowing access to a broad range of chiral diarylmethylamines in high yields (up to 98%) with uniformly excellent enantioselectivities (up to 99% ee). This catalyst system is also applicable to the arylation of N-tosyl arylimines. By utilizing this method, some biologically active molecules possessing a chiral 1-aryl-1,2,3,4-tetrahydroisoquinoline core such as Solifenacin and (S)-(+)-Cryptostyline II are facilely constructed.
Asymmetric synthesis method for preparation of solifenacin
-
, (2018/07/10)
The invention relates to an asymmetric synthesis method for preparation of solifenacin and specifically, discloses a preparation method of solifenacin. The method comprises that ortho-substituted aldehyde as a raw material undergoes a reaction under catalysis of rhodium and a chiral sulfoxide-olefin ligand to produce a key intermediate for high enantioselective addition, and the intermediate is further functionalized and cyclized to form solifenacin. The method is easy to operate, needs mild reaction conditions and has high efficiency and high selectivity.
Ethyl (S)-1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate Synthetic route And Reaction conditions
- 541-41-3
chloroformic acid ethyl ester
- 22990-19-8,96719-89-0,118864-75-8
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
- 180468-42-2
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions | Yield |
---|---|
100% | |
99% | |
Withpotassium carbonate;
1-butyl-3-methylimidazolium Tetrafluoroborate;
at 20 ℃;
for 2h;
Reagent/catalyst;
Concentration; | 97.9% |
95% | |
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline;Withtriethylamine;Indichloromethane;at 0 ℃;
for 0.166667h; | 90% |
89% | |
Withpotassium carbonate;Inwater;
toluene;at 10 - 25 ℃;
for 1 - 2h;
Product distribution / selectivity; | |
Withhydrogenchloride;Indichloromethane;
water;at 28 ℃;
for 0.166667h;
pH=~ 2;
Product distribution / selectivity; | |
13 g | |
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline;Withpotassium carbonate;Inwater;
toluene;at 20 ℃;
for 0.0833333h; |
- 52250-50-7
1-phenyl-3,4-dihydroisoquinoline
- 180468-42-2
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaBH4 / ethanol / 60 h / 20 °C 2: 100 percent / K2CO3 / CH2Cl2 / 20 °C | |
Multi-step reaction with 3 steps 1.1: methanol; sodium tetrahydroborate / water / 5.42 h / 20 - 34 °C 2.1: D-tartaric acid / methanol; ethyl acetate / 2.08 h / 28 - 64 °C / Resolution of racemate 2.2: 1.17 h / pH 8 - 9 3.1: sodium carbonate / toluene / 2.17 h / 0 - 28 °C |
- 3278-14-6
N-phenethylbenzamide
- 180468-42-2
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: P2O5; POCl3 / xylene / 2.5 h / Heating 2: NaBH4 / ethanol / 60 h / 20 °C 3: 100 percent / K2CO3 / CH2Cl2 / 20 °C | |
Multi-step reaction with 4 steps 1.1: PPA / water / 4.25 h / 14.9 - 165 °C 1.2: 0.17 h / 28 - 42 °C / pH 2.1 - 7.12 2.1: methanol; sodium tetrahydroborate / water / 5.42 h / 20 - 34 °C 3.1: D-tartaric acid / methanol; ethyl acetate / 2.08 h / 28 - 64 °C / Resolution of racemate 3.2: 1.17 h / pH 8 - 9 4.1: sodium carbonate / toluene / 2.17 h / 0 - 28 °C |
- 180272-45-1
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
- 180468-42-2
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / -10 - 20 °C 2.1: hydrogenchloride; water; phosphoric acid / 95 - 100 °C 2.2: 20 °C / pH 9 - 10 3.1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate 4.1: acetone / 5 °C / Reflux | |
Multi-step reaction with 3 steps 1.1: potassium carbonate / dichloromethane / 0 - 25 °C 2.1: sodium hydroxide / ethanol / 75 - 80 °C 2.2: Cooling 3.1: acetone / 5 °C / Reflux | |
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / -10 - 20 °C 2.1: hydrogenchloride; water; phosphoric acid / 32 h / 95 - 100 °C 2.2: 20 °C / pH 9 - 10 3.1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate 4.1: acetone / 5 °C / Reflux | |
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / -10 - 20 °C 2.1: hydrogenchloride; water; phosphoric acid / 95 - 100 °C 2.2: 20 °C / pH 9 - 10 3.1: D-tartaric acid / water / Resolution of racemate 3.2: 20 °C 4.1: acetone / 5 °C / Reflux |
- 881834-78-2
4-nitrophenyl-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
- 180468-42-2
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol / 75 - 80 °C 1.2: Cooling 2.1: triethylamine / dichloromethane / -10 - 20 °C 3.1: hydrogenchloride; water; phosphoric acid / 32 h / 95 - 100 °C 3.2: 20 °C / pH 9 - 10 4.1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate 5.1: acetone / 5 °C / Reflux | |
Multi-step reaction with 2 steps 1.1: sodium hydroxide / ethanol / 75 - 80 °C 1.2: Cooling 2.1: acetone / 5 °C / Reflux Withsodium hydroxide;Inethanol;
acetone; |
- 22990-19-8
1-phenyl-1,2,3,4-tetrahydroisoquinoline
- 180468-42-2
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate 2: acetone / 5 °C / Reflux WithD-tartaric acid;Inwater;
acetone; | |
Multi-step reaction with 2 steps 1.1: D-tartaric acid / water / Resolution of racemate 1.2: 20 °C 2.1: acetone / 5 °C / Reflux WithD-tartaric acid;Inwater;
acetone; | |
Multi-step reaction with 4 steps 1.1: D-tartaric acid / water / Resolution of racemate 1.2: 20 °C 2.1: potassium carbonate / dichloromethane / 0 - 25 °C 3.1: sodium hydroxide / ethanol / 75 - 80 °C 3.2: Cooling 4.1: acetone / 5 °C / Reflux | |
Multi-step reaction with 2 steps 1.1: D-tartaric acid / methanol; ethyl acetate / 2.08 h / 28 - 64 °C / Resolution of racemate 1.2: 1.17 h / pH 8 - 9 2.1: sodium carbonate / toluene / 2.17 h / 0 - 28 °C |
- 1300713-32-9
N-acetyl-(1R)-phenyl-1,2,3,4-tetrahydroisoquinoline
- 180468-42-2
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride; water; phosphoric acid / 32 h / 95 - 100 °C 1.2: 20 °C / pH 9 - 10 2.1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate 3.1: acetone / 5 °C / Reflux Withhydrogenchloride;
D-tartaric acid;
phosphoric acid;
water;Inwater;
acetone; |
- 1085541-60-1
N-chloroacetyl-(1R)-phenyl-1,2,3,4-tetrahydroisoquinoline
- 180468-42-2
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride; water; phosphoric acid / 95 - 100 °C 1.2: 20 °C / pH 9 - 10 2.1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate 3.1: acetone / 5 °C / Reflux Withhydrogenchloride;
D-tartaric acid;
phosphoric acid;
water;Inwater;
acetone; | |
Multi-step reaction with 3 steps 1.1: hydrogenchloride; water; phosphoric acid / 95 - 100 °C 1.2: 20 °C / pH 9 - 10 2.1: D-tartaric acid / water / Resolution of racemate 2.2: 20 °C 3.1: acetone / 5 °C / Reflux Withhydrogenchloride;
D-tartaric acid;
phosphoric acid;
water;Inwater;
acetone; | |
Multi-step reaction with 5 steps 1.1: hydrogenchloride; water; phosphoric acid / 95 - 100 °C 1.2: 20 °C / pH 9 - 10 2.1: D-tartaric acid / water / Resolution of racemate 2.2: 20 °C 3.1: potassium carbonate / dichloromethane / 0 - 25 °C 4.1: sodium hydroxide / ethanol / 75 - 80 °C 4.2: Cooling 5.1: acetone / 5 °C / Reflux |
- 74-96-4
ethyl bromide
- 124-38-9,18923-20-1
carbon dioxide
- 22990-19-8,96719-89-0,118864-75-8
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
- 180468-42-2
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions | Yield |
---|---|
84% |
- 180468-42-2
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / methanol; 1,4-dioxane / 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 0.17 h / 0 °C 2.2: 1 h / 20 °C |
Ethyl (S)-1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate Raw materials
- 541-41-3
chloroformic acid ethyl ester
- 22990-19-8
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
- 52250-50-7
1-phenyl-3,4-dihydroisoquinoline
- 3278-14-6
N-phenethylbenzamide
- 1035272-88-8
(S)-1,2,3,4-tetrahydro-1-phenyl-isoquinoline-2-carboxylic acid
Ethyl (S)-1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate Target Products
- 732228-02-3
(1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester
- 242478-37-1
solifenacin
- 740780-79-4
(3R)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylate
- 774517-20-3
(3S)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylate
- 22990-19-8
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Business Type:
- Lab/Research institutionsTrading CompanyManufacturers
Certificate:
- Product LicenseEnterprise AuthenticationISOGMPFDAHALAL
Country :
China (Mainland)(87)
India(2)
United States(2)
United Kingdom(1)
Recommended products
- 2-benzyl-1H-indene
- threo-L-(2S,3R)-β-methylphenylalanine
- 1,2-bis(ethylthio)ethane
- 2-(4-fluorophenyl)naphthalene
- 5-amino-2,3-dihydro-1,3,4-thiadiazole-2-thione
- 2-phenyl-4,5,6,7-tetrahydrobenzofuran
- 2-methyl-5-chloro-benzothiazole
- tetraphenyloxirane
- 4-methoxybenzyl phenyl sulfide
- 4-phenylcinnamic acid
- 3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one
- L-tropic acid-((1Ξ)-6exo-hydroxy-tropane-3endo-yl ester)
- orthobenzoic acid trimethyl ester
- seseline
- 1-(4-methoxyphenyl)-2-tosylethanone