3-amino-4-(1H-3-indolyl)butanenitrile | 66087-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-amino-4-(1H-3-indolyl)butanenitrile
• 英文别名: 3(S)-Amino-4(β-indolyl)butanonitril；3-amino-4-indol-3-yl-butyronitrile；3-amino-4-(1H-indol-3-yl)-butyronitrile；3-amino-4-(1H-indol-3-yl)butanenitrile
• CAS: 66087-99-8
• 化学式: C₁₂H₁₃N₃
• 分子量: 199.255
• InChiKey: CYLRMCLUUBXRRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  465.8±35.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-amino-4-(1H-3-indolyl)butanenitrile 在 盐酸 、 Candida antarctica lipase A*celite 作用下， 以 异丙醚 为溶剂， 反应 48.0h， 生成 3-amino-4-(1H-3-indolyl)butanoic acid ethyl ester
  参考文献：
  名称：

  Chemoenzymatic preparation of the enantiomers of β-tryptophan ethyl ester and the β-amino nitrile analogue

  摘要：

  Racemic alpha-tryptophan was chemoselectively transformed into the enantiomers of beta-tryptophan ethyl ester. The key step in achieving enantiopurity was the N-acylation of the 3-amino-4-(3-indolyl)butanenitrile intermediate with Candida antarctica lipase A (CAL-A). The enzymatic N-acylation of racemic beta-tryptophan ethyl ester was also studied. CAL-A was highly (R)-enantioselective in the present kinetic resolutions, leading to a mixture of the butanamide product with an (R)-configuration and the unreacted starting material with an (S)-configuration at 50% conversion. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.016
• 作为产物：
  描述：

  3-(2-nitrobenzenesulfonyl)amino-4-(1H-3-indolyl)butanenitrile 在 potassium carbonate 、 苯硫酚 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以99%的产率得到3-amino-4-(1H-3-indolyl)butanenitrile
  参考文献：
  名称：

  Chemoenzymatic preparation of the enantiomers of β-tryptophan ethyl ester and the β-amino nitrile analogue

  摘要：

  Racemic alpha-tryptophan was chemoselectively transformed into the enantiomers of beta-tryptophan ethyl ester. The key step in achieving enantiopurity was the N-acylation of the 3-amino-4-(3-indolyl)butanenitrile intermediate with Candida antarctica lipase A (CAL-A). The enzymatic N-acylation of racemic beta-tryptophan ethyl ester was also studied. CAL-A was highly (R)-enantioselective in the present kinetic resolutions, leading to a mixture of the butanamide product with an (R)-configuration and the unreacted starting material with an (S)-configuration at 50% conversion. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.016

文献信息

• Cyanomethyl substituted N-Acyl Tryptamines
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP2020404A1

  公开（公告）日：2009-02-04

  The present invention relates to cyanomethyl substituted N-acyl tryptamines of the formula I in which R1, R2, R3, R4, R5, Q, X and W have the meaning as defined in the description. The compounds according to the invention are effective FSH antagonists and can be used for example for fertility control in men or in women, or for the prevention and/or treatment of osteoporosis.

  本发明涉及具有以下结构的氰甲基取代的N-酰基色胺化合物，其中R1、R2、R3、R4、R5、Q、X和W的含义如描述中所定义。根据本发明的化合物是有效的FSH拮抗剂，可用于男性或女性的生育控制，或用于骨质疏松症的预防和/或治疗。
• Synthesis of 3-(indol-2-yl)-propenoate derivatives of tryptamine, valuable intermediates for the preparation of indole alkaloids
  作者：Patrick D Bailey、Sean P Hollinshead

  DOI：10.1016/s0040-4039(00)96233-6

  日期：1987.1

  A simple three step route to 3-(indol-2-yl)-propenoate derivatives of tryptamine has been developed, involving the base-induced ring-opening of protected tetrahydro-β-carbolines that result from a modified Pictet-Spengler reaction.

  已经开发了一种简单的三步合成色胺的3-（吲哚-2-基）-丙烯酸酯衍生物的方法，涉及碱诱导的由修饰的Pictet-Spengler反应产生的受保护的四氢-β-咔啉的开环。
• CYANOMETHYL SUBSTITUTED N-ACYL TRYPTAMINES
  申请人：WORTMANN Lars

  公开号：US20090069321A1

  公开（公告）日：2009-03-12

  The present invention relates to cyanomethyl substituted N-acyl tryptamines of the formula I in which R1, R2, R3, R4, R5, Q, X and W have the meaning as defined in the description. The compounds according to the invention are effective FSH antagonists and can be used for example for fertility control in men or in women, or for the prevention and/or treatment of osteoporosis.

  本发明涉及公式I中的氰甲基取代N-酰基色胺类化合物，其中R1、R2、R3、R4、R5、Q、X和W的含义如描述中所定义。本发明的化合物是有效的FSH拮抗剂，例如可以用于男性或女性的生育控制，或用于骨质疏松的预防和/或治疗。
• BAILEY, PATRICK D.;HOLLINSHEAD, SEAN P., TETRAHEDRON LETT., 28,(1987) N 25, 2879-2882
  作者：BAILEY, PATRICK D.、HOLLINSHEAD, SEAN P.

  DOI：——

  日期：——
• [EN] CYANOMETHYL SUBSTITUTED N-ACYL TRYPTAMINES<br/>[FR] N-ACYLTRYPTAMINES À SUBSTITUTION CYANOMÉTHYLE
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2009016253A2

  公开（公告）日：2009-02-05

  The present invention relates to cyanomethyl substituted N-acyl tryptamines of the formula (I) in which R1, R2, R3, R4, R5, Q, X and W have the meaning as defined in the description. The compounds according to the invention are effective FSH antagonists and can be used for example for fertility control in men or in women, or for the prevention and/or treatment of osteoporosis.