(3aS,7aR)-3a-hydroxy-1-(4-methoxybenzyl)-2-oxooctahydro-7aH-indole-7a-carboxylic acid | 1185252-55-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3aS,7aR)-3a-hydroxy-1-(4-methoxybenzyl)-2-oxooctahydro-7aH-indole-7a-carboxylic acid
• 英文别名: (3aS,7aR)-3a-hydroxy-1-[(4-methoxyphenyl)methyl]-2-oxo-4,5,6,7-tetrahydro-3H-indole-7a-carboxylic acid
• CAS: 1185252-55-4
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: YQKATTPMURRRTD-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,7aR)-3a-hydroxy-1-(4-methoxybenzyl)-2-oxooctahydro-7aH-indole-7a-carboxylic acid 在 三乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以67%的产率得到
  参考文献：
  名称：

  Propellane as a conformational device for the stabilization of the β-lactone of salinosporamide A

  摘要：

  The synthesis of a propellane derivative of salinosporamide A having increased stability under physiological-like conditions is reported. The synthesis took advantage of a substrate-controlled stereoselective Ugi 4-center 3-component reaction to construct the required syn-bicyclic pyroglutamic acid framework. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.085
• 作为产物：
  描述：

  (3aS,7aR)-1-(4-methoxybenzyl)-3a-[(methylsulfanyl)-methoxy]-2-oxooctahydro-7aH-indole-7a-carboxylic acid 在 trityl tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以85%的产率得到(3aS,7aR)-3a-hydroxy-1-(4-methoxybenzyl)-2-oxooctahydro-7aH-indole-7a-carboxylic acid
  参考文献：
  名称：

  Propellane as a conformational device for the stabilization of the β-lactone of salinosporamide A

  摘要：

  The synthesis of a propellane derivative of salinosporamide A having increased stability under physiological-like conditions is reported. The synthesis took advantage of a substrate-controlled stereoselective Ugi 4-center 3-component reaction to construct the required syn-bicyclic pyroglutamic acid framework. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.085

文献信息

• Synthesis of Bicyclic Pyroglutamic Acid Featuring the Ugi Reaction and a Unique Stereoisomerization at the Angular Position by Grob Fragmentation Followed by a Transannular Ketene [2+2] Cycloaddition Reaction
  作者：Yoshihisa Kobayashi、Mitchell Vamos、Kerem Ozboya

  DOI：10.1055/s-2007-982538

  日期：2007.6

  A stereoisomerization at the angular position of N-acylindoles during basic hydrolysis was discovered to give only the syn-bicyclic pyroglutamic acid, proceeding through a transannular [2+2] cycloaddition of a ketene-ketone intermediate generated by a Grob fragmentation.

  发现在碱性水解过程中，N-酰基吲哚的角位置发生了立体异构化，只产生了合成双环焦谷氨酸，其过程是通过格劳博碎裂生成的酮中间体进行反环状[2+2]环加成反应。