diethyl 1-cyclopentene-3,5-diacetate | 1085395-81-8

• 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: diethyl 1-cyclopentene-3,5-diacetate
• 英文别名: Ethyl 2-[4-(2-ethoxy-2-oxoethyl)cyclopent-2-en-1-yl]acetate
• CAS: 1085395-81-8
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: AKLUZXJQNDXFHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 1-cyclopentene-3,5-diacetate 在 sodium 作用下， 以 various solvent(s) 为溶剂， 反应 18.0h， 生成 (1S,6R)-4-hydroxybicyclo[4.2.1]non-7-en-3-one
  参考文献：
  名称：

  Stereoselective synthesis of (±)-tacamonine

  摘要：

  We report a stereocontrolled approach to the pentacyclic indole alkaloid tacamonine by modifying an earlier route using norbornadiene to supply the nontryptamine portion. By maintaining a bridged system the reduction step of the Bischler-Napieralski reaction proceeded to deliver a bridged diol in which three methine hydrogen atoms are in an all-cis configuration. All 19 skeletal carbon atoms are fully incorporated, therefore, the only remaining steps involved cleavage of the vic-diol subunit in the seven-membered ring and further oxidation and reduction of the resulting lactam alclehyde. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.049