5-(2,2-diphenylcyclopropyl)-4-pentenoic acid | 228860-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(2,2-diphenylcyclopropyl)-4-pentenoic acid
• 英文别名: 5-(2,2-diphenylcyclopropyl)pent-4-enoic acid
• CAS: 228860-00-2
• 化学式: C₂₀H₂₀O₂
• 分子量: 292.378
• InChiKey: OJLBWBVMQJAGMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-(2,2-diphenylcyclopropyl)-4-pentenoic acid 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 jones reagent 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 、 丙酮 、 苯 为溶剂， 反应 4.58h， 生成 (E)-5-(2,2-diphenylcyclopropyl)-4-pentenoic acid 2-thioxo-2H-pyridin-1-yl ester
  参考文献：
  名称：

  Direct Measurements of the Kinetics of 3-exo Radical Cyclizations Using Radical Reporter Groups

  摘要：

  The E and Z isomers of the 4-(2,2-diphenylcyclopropyl)-3-butenyl radical (1), produced by laser flash photolysis of the corresponding PTOC esters in THF, cyclized to the (2,2-diphenylcyclopropyl)(cyclopropyl)methyl radical (2) that rapidly opened to 1,1-diphenyl-4-cyclopropyl-3-butenyl radicals (3). Radicals 3 were monitored by UV spectroscopy, but the observed rate constants were for the initial, relatively slow cyclizations of radicals 1 to radical 2. The Arrhenius functions determined in the temperature range of 20-58 degrees C were log(k/s(-1)) = (11.46 +/- 0.38) - (9.10 +/- 0.54)/theta for (E)-1 and log(k/s(-1)) = (12.34 +/- 0.32) - (10.10 +/- 0.45)/theta for (Z)-1 where theta = 2.3RT in kcal/mol and errors are at 2 sigma. Radical (Z)-1 cyclizes somewhat faster than radical (E)-1 as a result of a more favorable entropy of activation and despite the fact that the activation energy for cyclization of(Z)-1 through the requisite syn-transition state is greater than that for cyclization of (E)-1 through an anti-transition state.

  DOI：

  10.1021/jo990129v
• 作为产物：
  描述：

  2,2-diphenylcyclopropanecarbaldehyde 、 (3-丙羧基)三苯基溴化膦 生成 5-(2,2-diphenylcyclopropyl)-4-pentenoic acid
  参考文献：
  名称：

  通过光敏形式 [5+2] 环加成立体选择性构建环庚烯稠合二氢吲哚骨架

  摘要：

  在芳族酮的敏化下，通过高压汞灯通过 Pyrex 玻璃照射在酰基侧链末端具有乙烯基环丙烷部分的 1-酰基吲哚衍生物，可以立体选择性地以高产率得到相应的环化产物。产物的分布高度依赖于环丙烷环上的取代基。在简单的环丙烷的情况下，产物是扩环的环庚烯稠合二氢吲哚和全顺式稠合环丙基环丁烷稠合二氢吲哚通过 [2 + 2] 环加成的混合物，而环庚烯稠合二氢吲哚主要通过正式 [在取代环丙烷的情况下，5 + 2] 环化。特别是，在甲硅烷基环丙烷的情况下，产物选择性非常高。

  DOI：

  10.1016/j.tetlet.2021.153588

文献信息

• Stereoselective construction of cycloheptene-fused indoline frameworks through photosensitised formal [5+2] cycloaddition
  作者：Noriyoshi Arai、Takeshi Ohkuma

  DOI：10.1016/j.tetlet.2021.153588

  日期：2022.1

  Irradiation of 1-acylindole derivatives that possess a vinylcyclopropane moiety at the end of the acyl side chain by a high-pressure mercury lamp through Pyrex glass under sensitization of an aromatic ketone gave the corresponding cyclised products stereoselectively in high yields. The distribution of the products was highly dependent on the substituents on the cyclopropane ring. In the case of a simple

  在芳族酮的敏化下，通过高压汞灯通过 Pyrex 玻璃照射在酰基侧链末端具有乙烯基环丙烷部分的 1-酰基吲哚衍生物，可以立体选择性地以高产率得到相应的环化产物。产物的分布高度依赖于环丙烷环上的取代基。在简单的环丙烷的情况下，产物是扩环的环庚烯稠合二氢吲哚和全顺式稠合环丙基环丁烷稠合二氢吲哚通过 [2 + 2] 环加成的混合物，而环庚烯稠合二氢吲哚主要通过正式 [在取代环丙烷的情况下，5 + 2] 环化。特别是，在甲硅烷基环丙烷的情况下，产物选择性非常高。
• Direct Measurements of the Kinetics of 3-<i>e</i><i>xo</i> Radical Cyclizations Using Radical Reporter Groups
  作者：Eldi Furxhi、John H. Horner、Martin Newcomb

  DOI：10.1021/jo990129v

  日期：1999.5.1

  The E and Z isomers of the 4-(2,2-diphenylcyclopropyl)-3-butenyl radical (1), produced by laser flash photolysis of the corresponding PTOC esters in THF, cyclized to the (2,2-diphenylcyclopropyl)(cyclopropyl)methyl radical (2) that rapidly opened to 1,1-diphenyl-4-cyclopropyl-3-butenyl radicals (3). Radicals 3 were monitored by UV spectroscopy, but the observed rate constants were for the initial, relatively slow cyclizations of radicals 1 to radical 2. The Arrhenius functions determined in the temperature range of 20-58 degrees C were log(k/s(-1)) = (11.46 +/- 0.38) - (9.10 +/- 0.54)/theta for (E)-1 and log(k/s(-1)) = (12.34 +/- 0.32) - (10.10 +/- 0.45)/theta for (Z)-1 where theta = 2.3RT in kcal/mol and errors are at 2 sigma. Radical (Z)-1 cyclizes somewhat faster than radical (E)-1 as a result of a more favorable entropy of activation and despite the fact that the activation energy for cyclization of(Z)-1 through the requisite syn-transition state is greater than that for cyclization of (E)-1 through an anti-transition state.