5-Oxo-bicyclo[2.2.2]oct-2-ene-1,2,3-tricarboxylic acid 1-tert-butyl ester 2,3-dimethyl ester | 476153-62-5

• 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: 5-Oxo-bicyclo[2.2.2]oct-2-ene-1,2,3-tricarboxylic acid 1-tert-butyl ester 2,3-dimethyl ester
• 英文别名: 1-O-tert-butyl 2-O,3-O-dimethyl 5-oxobicyclo[2.2.2]oct-2-ene-1,2,3-tricarboxylate
• CAS: 476153-62-5
• 化学式: C₁₇H₂₂O₇
• 分子量: 338.357
• InChiKey: YPKFTFAYXMCFGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-Oxo-bicyclo[2.2.2]oct-2-ene-1,2,3-tricarboxylic acid 1-tert-butyl ester 2,3-dimethyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 5-Oxo-bicyclo[2.2.2]oct-2-ene-1,2,3-tricarboxylic acid 2,3-dimethyl ester
  参考文献：
  名称：

  Regiospecific synthesis of a bridgehead-functionalized bicyclo[2.2.2]octenone

  摘要：

  Three independent strategies are tested toward the synthesis of the protected 1-aminobicyclo[2.2.2]octene ketodiester 1. One of these three is found to be completely regioselective. It proceeds by Diels-Alder addition of dimethyl acetylenedicarboxylate to the silyl enol ether of 3-benzyloxycarbonyl-2-cyclohexenone, followed by a chemoselective Curtius rearrangement. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01065-1
• 作为产物：
  描述：

  5-Hydroxy-bicyclo[2.2.2]oct-2-ene-1,2,3-tricarboxylic acid 1-tert-butyl ester 2,3-dimethyl ester 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 5-Oxo-bicyclo[2.2.2]oct-2-ene-1,2,3-tricarboxylic acid 1-tert-butyl ester 2,3-dimethyl ester
  参考文献：
  名称：

  Regiospecific synthesis of a bridgehead-functionalized bicyclo[2.2.2]octenone

  摘要：

  Three independent strategies are tested toward the synthesis of the protected 1-aminobicyclo[2.2.2]octene ketodiester 1. One of these three is found to be completely regioselective. It proceeds by Diels-Alder addition of dimethyl acetylenedicarboxylate to the silyl enol ether of 3-benzyloxycarbonyl-2-cyclohexenone, followed by a chemoselective Curtius rearrangement. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01065-1