2-cyano-3-(2,2-dimethyl-[1,3]dioxolan-4-ylmethylene)acrylic acid methyl ester | 171110-24-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-cyano-3-(2,2-dimethyl-[1,3]dioxolan-4-ylmethylene)acrylic acid methyl ester
• 英文别名: methyl (E)-2-cyano-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 171110-24-0
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: COULFTRNSKOKFF-IPWDFOCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  碘化异丙基三苯鏻 、 2-cyano-3-(2,2-dimethyl-[1,3]dioxolan-4-ylmethylene)acrylic acid methyl ester 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 25.0h， 以67%的产率得到methyl 1-cyano-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethylcyanopropanecarboxylate
  参考文献：
  名称：

  Hemisynthesis of methyl pyrethroates from γ-alkoxy-alkylidene malonates and isopropylidenediphenylsulfurane and isopropylidenetriphenylphosphorane

  摘要：

  Hemi synthesis of methyl pyrethroates from gamma-alkoxy-alkylidene malonates and isopropylidenediphenylsulfurane and isopropylidenetriphenylphosphorane is disclosed. It takes advantage of the high degree of stereocontrol observed in the cyclopropanation of gamma-alkoxy-alkylidene malonates by the above mentioned ylides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.035
• 作为产物：
  描述：

  氰乙酸甲酯 、 双丙酮-D-甘露糖醇 在 lead(IV) acetate 、 乙酸酐 作用下， 生成 2-cyano-3-(2,2-dimethyl-[1,3]dioxolan-4-ylmethylene)acrylic acid methyl ester
  参考文献：
  名称：

  Jimenez, Blanca; Martin, Nazario; Martinez-Grau, Angeles, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 4, p. 1381 - 1384

  摘要：

  DOI：

文献信息

• Methyl (1R,2R)- and (1S,2S)-1-Cyano-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropane-1-carboxylate
  作者：C. Cativiela、M. D. Díaz-de-Villegas、J. A. Gálvez、A. I. Jiménez、M. P. López

  DOI：10.1107/s0108270196010281

  日期：1996.12.15

  In the title diastereomeric compounds, C11H15NO4, the methyl ester group adopts a bisecting conformation with the carbonyl O atom eclipsing the cyclopropane ring. In the crystals of both compounds, the molecules are piled up along one of the crystallographic axes.
• Jimenez, Blanca; Martin, Nazario; Martinez-Grau, Angeles, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 4, p. 1381 - 1384
  作者：Jimenez, Blanca、Martin, Nazario、Martinez-Grau, Angeles、Seoane, Carlos、Marco, Jose L.

  DOI：——

  日期：——
• Hemisynthesis of methyl pyrethroates from γ-alkoxy-alkylidene malonates and isopropylidenediphenylsulfurane and isopropylidenetriphenylphosphorane
  作者：Alain Krief、Alexandre Froidbise

  DOI：10.1016/j.tet.2004.06.035

  日期：2004.8

  Hemi synthesis of methyl pyrethroates from gamma-alkoxy-alkylidene malonates and isopropylidenediphenylsulfurane and isopropylidenetriphenylphosphorane is disclosed. It takes advantage of the high degree of stereocontrol observed in the cyclopropanation of gamma-alkoxy-alkylidene malonates by the above mentioned ylides. (C) 2004 Elsevier Ltd. All rights reserved.