(3β)-3-<(3-hydroxy-17-oxoandrost-4-en-3-yl)ethynyl>-1H-indole-1-carboxylic acid, 1,1-dimethylethyl ester | 156539-41-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3β)-3-<(3-hydroxy-17-oxoandrost-4-en-3-yl)ethynyl>-1H-indole-1-carboxylic acid, 1,1-dimethylethyl ester
• 英文别名: (3β)-3-[(3-hydroxy-17-oxoandrost-4-en-3-yl)ethynyl]-1H-indole-1-carboxylic acid, 1,1-dimethylethyl ester；tert-butyl 3-[2-[(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-17-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-yl]ethynyl]indole-1-carboxylate
• CAS: 156539-41-2
• 化学式: C₃₄H₄₁NO₄
• 分子量: 527.704
• InChiKey: LPJZFSDJTFKALN-MAXLMSOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  39
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3β)-3-<(3-hydroxy-17-oxoandrost-4-en-3-yl)ethynyl>-1H-indole-1-carboxylic acid, 1,1-dimethylethyl ester 在 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以66%的产率得到(3β)-3-<2-(3-hydroxy-17-oxoandrost-4-en-3-yl)ethyl>-1H-indole-1-carboxylic acid, 1,1-dimethylethyl ester
  参考文献：
  名称：

  A facile method to append peptidal side-chains onto steroidal templates.

  摘要：

  Side-chains corresponding to phenylalanine, tyrosine and tryptophan are introduced onto a steroid template in a highly efficient manner via a condensation of the appropriate lithium acetylide with a steroidal ketone. The subsequent acetylene functionality can be selectively reduced in the presence of a modified benzyl ether and steroid ring unsaturation.

  DOI：

  10.1016/s0040-4020(01)86716-8
• 作为产物：
  描述：

  3-甲酰基吲哚酸-1-羧酸 t-丁基酯 在 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 9.25h， 生成 (3β)-3-<(3-hydroxy-17-oxoandrost-4-en-3-yl)ethynyl>-1H-indole-1-carboxylic acid, 1,1-dimethylethyl ester
  参考文献：
  名称：

  A facile method to append peptidal side-chains onto steroidal templates.

  摘要：

  Side-chains corresponding to phenylalanine, tyrosine and tryptophan are introduced onto a steroid template in a highly efficient manner via a condensation of the appropriate lithium acetylide with a steroidal ketone. The subsequent acetylene functionality can be selectively reduced in the presence of a modified benzyl ether and steroid ring unsaturation.

  DOI：

  10.1016/s0040-4020(01)86716-8

文献信息

• A facile method to append peptidal side-chains onto steroidal templates.
  作者：David C. Horwell、Ian C. Lennon、Edward Roberts

  DOI：10.1016/s0040-4020(01)86716-8

  日期：1994.4

  Side-chains corresponding to phenylalanine, tyrosine and tryptophan are introduced onto a steroid template in a highly efficient manner via a condensation of the appropriate lithium acetylide with a steroidal ketone. The subsequent acetylene functionality can be selectively reduced in the presence of a modified benzyl ether and steroid ring unsaturation.