2-octylidenecyclopropanecarbaldehyde | 1171108-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 2-octylidenecyclopropanecarbaldehyde
• 英文别名: 2-Octylidenecyclopropane-1-carbaldehyde；2-octylidenecyclopropane-1-carbaldehyde
• CAS: 1171108-02-3
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: QCBGHIRWJYETPP-UHFFFAOYSA-N

物化性质

• 沸点：
  253.9±29.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-octylidenecyclopropanecarbaldehyde 在 palladium diacetate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以75%的产率得到(E,E)-2,4-十二碳二烯醛
  参考文献：
  名称：

  Pd(0) or Pd(II)-catalyzed ring-opening reactions of benzylidene- and alkylidenecyclopropyl ketones and aldehydes

  摘要：

  Pd(0) catalyzed reactions of methylenecyclopropyl carbonyl compounds afforded a convenient method for the synthesis of conjugate (E,E)-1,3-diene derivatives 2 in good to excellent yields. Moreover, we also found that Pd(II)-catalyzed reactions of methylenecyclopropyl carbonyl compounds with water gave 1,5-diketones in good to high yields via a carbene-palladium intermediate. The plausible reaction mechanisms have also been provided on the basis of control and O-18-labeling experiments. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.044
• 作为产物：
  描述：

  (2-octylidenecyclopropyl)methanol 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 生成 2-octylidenecyclopropanecarbaldehyde
  参考文献：
  名称：

  A Synthetic Protocol of Trans-Substituted Cyclopentenes via the Ring-Opening Rearrangement of MCP Alkenyl Derivatives

  摘要：

  A efficient method to stereospecifically synthesize trans-substituted cyclopentene derivatives via the ring-opening rearrangement of readily available MCP alkenyl derivatives in moderate to good yields has been described. The control experiment based on the deuterium labeling experiment and the addition of TEMPO revealed that this transformation might proceed through a fast concerted pericyclic process rather than a simple radical pathway or an ionic pathway.

  DOI：

  10.1021/jo902512q

文献信息

• HOTf-Catalyzed Rearrangement of Methylenecyclopropane Aryl and Alkyl Alcohols
  作者：Xiang-Ying Tang、Min Shi

  DOI：10.1002/ejoc.201000509

  日期：2010.7

  An efficient method to synthesize multisubstituted naphthalene and cyclobutanol derivatives through ring opening/ring enlargement of readily available methylenecyclopropane diaryl alcohols or dialkyl- and monoalkyl- as well as monoaryl alcohols in moderate to good yields has been described in this paper. The formation of naphthalene derivatives is a sequential reaction involving a cation-induced ring

  本文描述了一种通过容易获得的亚甲基环丙烷二芳醇或二烷基和单烷基以及单芳醇的开环/扩环来合成多取代萘和环丁醇衍生物的有效方法，产率中等至良好。萘衍生物的形成是一个连续反应，包括环丙烷的阳离子诱导开环、Friedel Crafts 烷基化反应，然后是芳构化。另一方面，环丁醇衍生物的生产是一个阳离子诱导的扩环过程。还介绍了范围和限制。
• An Efficient Route to 2-Substituted<i>N</i>-(1-Amino-3-methylpyrrol)amides by Ring-Opening Cyclization of Benzylidene- and Alkylidenecyclopropylcarbaldehydes with Hydrazides
  作者：Xiang-Ying Tang、Min Shi

  DOI：10.1021/jo900730t

  日期：2009.8.21

  A convenient and efficient synthetic method for the construction of 2,3-disubstituted pyrrolamides in moderate to good Yields is established. The in situ generated water significantly accelerates the reaction rate. A possible mechanism involving the cascade ring-opening and thermal-induced rearrangement to produce the five-membered ring is proposed.
• A Synthetic Protocol of Trans-Substituted Cyclopentenes via the Ring-Opening Rearrangement of MCP Alkenyl Derivatives
  作者：Xiang-Ying Tang、Min Shi

  DOI：10.1021/jo902512q

  日期：2010.2.5

  A efficient method to stereospecifically synthesize trans-substituted cyclopentene derivatives via the ring-opening rearrangement of readily available MCP alkenyl derivatives in moderate to good yields has been described. The control experiment based on the deuterium labeling experiment and the addition of TEMPO revealed that this transformation might proceed through a fast concerted pericyclic process rather than a simple radical pathway or an ionic pathway.
• Pd(0) or Pd(II)-catalyzed ring-opening reactions of benzylidene- and alkylidenecyclopropyl ketones and aldehydes
  作者：Xiang-Ying Tang、Min Shi

  DOI：10.1016/j.tet.2009.08.044

  日期：2009.10

  Pd(0) catalyzed reactions of methylenecyclopropyl carbonyl compounds afforded a convenient method for the synthesis of conjugate (E,E)-1,3-diene derivatives 2 in good to excellent yields. Moreover, we also found that Pd(II)-catalyzed reactions of methylenecyclopropyl carbonyl compounds with water gave 1,5-diketones in good to high yields via a carbene-palladium intermediate. The plausible reaction mechanisms have also been provided on the basis of control and O-18-labeling experiments. (c) 2009 Elsevier Ltd. All rights reserved.