2,2-divinylcyclopropanecarboxylic acid | 1312331-01-3

• 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: 2,2-divinylcyclopropanecarboxylic acid
• 英文别名: 2,2-Bis(ethenyl)cyclopropane-1-carboxylic acid
• CAS: 1312331-01-3
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: DVYNTRNLIKLALI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-divinylcyclopropanecarboxylic acid 在 Hoveyda-Grubbs catalyst second generation 、 偶氮二异丁腈 、 1-氯-N,N,2-三甲基丙烯胺 、 potassium tert-butylate 、 三正丁基氢锡 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 生成 meloscine
  参考文献：
  名称：

  Highly functionalized donor–acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids

  摘要：

  A series of highly substituted vinylcyclopropanes were prepared and examined as reaction partners in a palladium-catalyzed (3+2) cycloaddition with nitrostyrenes. Described herein are our efforts to synthesize an elusive 1,1-divinylcyclopropane by several distinct approaches, and to apply surrogates of this fragment toward the synthesis of the Melodious alkaloids. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.016
• 作为产物：
  描述：

  ethyl 1,1-bis(benzyloxymethyl)cyclopropane-2-carboxylate 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 氢气 、 palladium(II) hydroxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， -78.0~20.0 ℃ 、413.7 kPa 条件下， 生成 2,2-divinylcyclopropanecarboxylic acid
  参考文献：
  名称：

  Highly functionalized donor–acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids

  摘要：

  A series of highly substituted vinylcyclopropanes were prepared and examined as reaction partners in a palladium-catalyzed (3+2) cycloaddition with nitrostyrenes. Described herein are our efforts to synthesize an elusive 1,1-divinylcyclopropane by several distinct approaches, and to apply surrogates of this fragment toward the synthesis of the Melodious alkaloids. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.016

文献信息

• Radical [3 + 2]-Annulation of Divinylcyclopropanes: Rapid Synthesis of Complex Meloscine Analogs
  作者：Hanmo Zhang、Kyu Ok Jeon、E. Ben Hay、Steven J. Geib、Dennis P. Curran、Matthew G. LaPorte

  DOI：10.1021/ol403078e

  日期：2014.1.3

  A radical [3 + 2]-divinylcyclopropane annulation cascade has been extended to encompass five D-ring variants of the meloscine/epimeloscine core structure. Representative ABCD tetracyclic intermediates were further elaborated with novel substituted E-rings through subsequent transformations of advanced intermediates that provided opportunities for late-stage variation of the B-ring (lactam) N-substituents which were also developed.
• A Short Total Synthesis of (±)-Epimeloscine and (±)-Meloscine Enabled by a Cascade Radical Annulation of a Divinylcyclopropane
  作者：Hanmo Zhang、Dennis P. Curran

  DOI：10.1021/ja2042854

  日期：2011.7.13

  The first stereoselective synthesis of epimeloscine has been accomplished in 13 total steps with a longest linear sequence of 10 steps. The core of the synthesis takes only five steps, the key ones being acylation, stereoselective tandem radical cyclization of a divinylcyclopropane to make two rings, and group-selective ring-closing metathesis of the resulting divinylcyclopentane to make the last ring.
• Highly functionalized donor–acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids
  作者：Alexander F.G. Goldberg、Robert A. Craig、Nicholas R. O’Connor、Brian M. Stoltz

  DOI：10.1016/j.tetlet.2014.09.016

  日期：2015.6

  A series of highly substituted vinylcyclopropanes were prepared and examined as reaction partners in a palladium-catalyzed (3+2) cycloaddition with nitrostyrenes. Described herein are our efforts to synthesize an elusive 1,1-divinylcyclopropane by several distinct approaches, and to apply surrogates of this fragment toward the synthesis of the Melodious alkaloids. (C) 2014 Elsevier Ltd. All rights reserved.