trans-trimethyl [4-D]cyclopent-3-ene-1,2,3-tricarboxylate

• 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: trans-trimethyl [4-D]cyclopent-3-ene-1,2,3-tricarboxylate
• 英文别名: trimethyl (1R,2S)-4-deuteriocyclopent-3-ene-1,2,3-tricarboxylate
• 化学式: C₁₁H₁₄O₆
• 分子量: 243.221
• InChiKey: KRDBFCOQRLTULS-DVLMDORBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-丁二烯酸甲酯 、 富马酸二甲酯 在 三苯基膦 重水 作用下， 以 苯 为溶剂， 生成 trans-trimethyl cyclopent-3-ene-1,2,3-tricarboxylate 、 trans-trimethyl [4-D]cyclopent-3-ene-1,2,3-tricarboxylate
  参考文献：
  名称：

  An Unexpected Role of a Trace Amount of Water in Catalyzing Proton Transfer in Phosphine-Catalyzed (3 + 2) Cycloaddition of Allenoates and Alkenes

  摘要：

  Through the joint forces of computation and experiment, the detailed mechanism of the Lu phosphine catalyzed (3 + 2) cycloaddition of allenoates and alkenes has been elucidated. The overall potential energy surface of the Lu (3 + 2) reaction has been computed. More importantly, theory and experiment have confirmed that a trace amount of water plays a critical role in assisting the process of [1,2] proton shift in the Lu reaction.

  DOI：

  10.1021/ja068215h

文献信息

• An Unexpected Role of a Trace Amount of Water in Catalyzing Proton Transfer in Phosphine-Catalyzed (3 + 2) Cycloaddition of Allenoates and Alkenes
  作者：Yuanzhi Xia、Yong Liang、Yuanyuan Chen、Ming Wang、Lei Jiao、Feng Huang、Song Liu、Yahong Li、Zhi-Xiang Yu

  DOI：10.1021/ja068215h

  日期：2007.3.1

  Through the joint forces of computation and experiment, the detailed mechanism of the Lu phosphine catalyzed (3 + 2) cycloaddition of allenoates and alkenes has been elucidated. The overall potential energy surface of the Lu (3 + 2) reaction has been computed. More importantly, theory and experiment have confirmed that a trace amount of water plays a critical role in assisting the process of [1,2] proton shift in the Lu reaction.