2-Cyclopropene-1,1-dicarboxylic acid, 2-propyl-, dimethyl ester | 90311-68-5

• 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: 2-Cyclopropene-1,1-dicarboxylic acid, 2-propyl-, dimethyl ester
• 英文别名: dimethyl 2-propylcycloprop-2-ene-1,1-dicarboxylate
• CAS: 90311-68-5
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: ZIZNXYAOEBABGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  苯甲醛 、 2-Cyclopropene-1,1-dicarboxylic acid, 2-propyl-, dimethyl ester 在 三(4-甲氧苯基)膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 30.0h， 以63%的产率得到(E)-2-(methoxycarbonyl)-5-phenyl-3-propyl-2,4-pentadienoic acid methyl ester
  参考文献：
  名称：

  Unexpected Regioselectivity Switch: Organophosphine-Triggered Reactions of Cyclopropene-1,1-dicarboxylates with Aldehydes

  摘要：

  With tris(4-methoxyphenyl)phosphine as the nucleophilic reagent, the readily available cyclopropene-1,1-dicarboxylates undergo a ring-opening reaction to generate a Wittig-type intermediate, which would react with aromatic aldehydes to yield (E)-5-aryl-2-(methoxycarbonyl)-2,4-pentadienoates. It is interesting to observe that the regioselectivity of the ring-opening reaction is switched.

  DOI：

  10.1021/ol401324z
• 作为产物：
  描述：

  2-叠氮丙二酸二甲酯 、 1-戊炔 以63%的产率得到
  参考文献：
  名称：

  ANAC, O.;AYDOGAN, A. C.;YAGCI, Y., CHIM. ACTA TURC., 1983, 11, N 2, 221-226

  摘要：

  DOI：

文献信息

• Diastereoselective organophotocatalytic hydrosulfonylation of cyclopropenes
  作者：Palasetty Chandu、Sourabh Biswas、Sumit Garai、Devarajulu Sureshkumar

  DOI：10.1039/d3gc03303a

  日期：——

  Herein, we present a remarkably efficient, highly diastereoselective organophotoredox-catalyzed hydrosulfonylation of cyclopropenes. This method employs sodium sulfinates to successfully construct poly-substituted sulfonated cyclopropane derivatives. To enhance the applicability of this transformation, we demonstrate its broad applicability across a wide range of substrates, its scalability for large-scale

  在此，我们提出了一种非常有效、高度非对映选择性的有机光氧化还原催化的环丙烯氢磺酰化反应。该方法利用亚磺酸钠成功构建了多取代磺化环丙烷衍生物。为了增强这种转化的适用性，我们展示了其在各种底物中的广泛适用性、大规模合成的可扩展性以及与后期功能化的兼容性。值得注意的是，这种后期功能化方案对不同的官能团表现出良好的耐受性。其操作便利性进一步增加了其吸引力，提供了在药物发现和药物化学中具有重要意义的有价值的构建模块。
• RhII-catalyzed cycloadditions of carbomethoxy iodonium ylides
  作者：Christina Batsila、George Kostakis、Lazaros P Hadjiarapoglou

  DOI：10.1016/s0040-4039(02)01260-1

  日期：2002.8

  Carbomethoxy iodonium ylides, generated from methyl acetoacetate and methyl malonate, respectively, are exploited in synthesis of cyclopropanes, cyclopropenes as well as various heterocycles. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Unexpected Regioselectivity Switch: Organophosphine-Triggered Reactions of Cyclopropene-1,1-dicarboxylates with Aldehydes
  作者：Shengjun Ni、Jie Chen、Shengming Ma

  DOI：10.1021/ol401324z

  日期：2013.7.5

  With tris(4-methoxyphenyl)phosphine as the nucleophilic reagent, the readily available cyclopropene-1,1-dicarboxylates undergo a ring-opening reaction to generate a Wittig-type intermediate, which would react with aromatic aldehydes to yield (E)-5-aryl-2-(methoxycarbonyl)-2,4-pentadienoates. It is interesting to observe that the regioselectivity of the ring-opening reaction is switched.
• ANAC, O.;AYDOGAN, A. C.;YAGCI, Y., CHIM. ACTA TURC., 1983, 11, N 2, 221-226
  作者：ANAC, O.、AYDOGAN, A. C.、YAGCI, Y.

  DOI：——

  日期：——