ethyl (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate | 1158945-78-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: ethyl (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• 英文别名: ethyl (1R,3R)-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate；ethyl (1R,3R)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1158945-78-8
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: PVOZBOVBXZLVEO-VQIMIIECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride 在 potassium carbonate 作用下， 以 水 、 乙酸乙酯 为溶剂， 生成 ethyl (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Syntheses of chiral 1,3-disubstituted tetrahydro-β-carbolines via CIAT process: highly stereoselective Pictet–Spengler reaction of d-tryptophan ester hydrochlorides with various aldehydes

  摘要：

  A highly stereoselective Pictet-Spengler reaction of D-tryptophan methyl ester hydrochloride 1-HCl with various aldehydes via a CIAT (crystallization-induced asymmetric transformation) process is described. It was revealed that the CIAT process should be performed in a mixed solvent of nitromethane and toluene, and a fine tuning of the ratio of nitromethane and toluene for each epimer Mixture of 2-HCl was necessary in order to get as high yields and stereoselectivities as possible. Enantiomerically pure cis (or trans) 1,3-disubstituted tetrahydro-beta-carbolines 2a-2v were obtained by recrystallization or flash chromatography after neutralization of the corresponding hydrochloride salts cis-2-HCl or trans-2-HCl. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.01.026

文献信息

• Conversion of tryptophan into ß-carboline derivatives
  申请人：LEK Pharmaceuticals d.d.

  公开号：EP2107059A1

  公开（公告）日：2009-10-07

  The invention belongs in the field of organic chemistry and relates to a new shortened Pictet-Spengler type reaction for preparing isomerically pure β-carboline compounds useful for the synthesis of tadalafil.

  这项发明属于有机化学领域，涉及一种用于制备同分异构纯度β-咔啉化合物的新型缩短的Pictet-Spengler型反应，该化合物对于制备他达拉非（tadalafil）非常有用。
• Nucleic acids encoding engineered imine reductases
  申请人：CODEXIS, INC.

  公开号：US10308966B2

  公开（公告）日：2019-06-04

  The present disclosure provides engineered polypeptides having imine reductase activity, polynucleotides encoding the engineered imine reductases, host cells capable of expressing the engineered imine reductases, and methods of using these engineered polypeptides with a range of ketone and amine substrate compounds to prepare secondary and tertiary amine product compounds.

  本公开提供了具有亚胺还原酶活性的工程多肽、编码工程亚胺还原酶的多核苷酸、能够表达工程亚胺还原酶的宿主细胞，以及使用这些工程多肽与一系列酮和胺底物化合物制备仲胺和叔胺产物化合物的方法。
• Engineered imine reductases and methods for the reductive amination of ketone and amine compounds
  申请人：Codexis, Inc.

  公开号：US10370648B2

  公开（公告）日：2019-08-06

  The present application provides engineered polypeptides having imine reductase activity, polynucleotides encoding the engineered imine reductases, host cells capable of expressing the engineered imine reductases, and methods of using these engineered polypeptides with a range of ketone and amine substrate compounds to prepare secondary and tertiary amine product compounds.

  本申请提供了具有亚胺还原酶活性的工程多肽、编码工程亚胺还原酶的多核苷酸、能够表达工程亚胺还原酶的宿主细胞，以及使用这些工程多肽与一系列酮和胺底物化合物制备仲胺和叔胺产物化合物的方法。
• ENGINEERED IMINE REDUCTASES AND METHODS FOR THE REDUCTIVE AMINATION OF KETONE AND AMINE COMPOUNDS
  申请人：Codexis, Inc.

  公开号：EP2847214B1

  公开（公告）日：2017-12-27
• Engineered imine reductases and methods for the reductive animation of ketone and amine compounds.
  申请人：Haibin CHEN

  公开号：US20130302859A1

  公开（公告）日：2013-11-14

  The present disclosure provides engineered polypeptides having imine reductase activity, polynucleotides encoding the engineered imine reductases, host cells capable of expressing the engineered imine reductases, and methods of using these engineered polypeptides with a range of ketone and amine substrate compounds to prepare secondary and tertiary amine product compounds.