Dimethyl 2-but-3-enyl-2-cyclohex-2-en-1-ylpropanedioate | 1401735-40-7

• 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: Dimethyl 2-but-3-enyl-2-cyclohex-2-en-1-ylpropanedioate
• 英文别名: dimethyl 2-but-3-enyl-2-cyclohex-2-en-1-ylpropanedioate
• CAS: 1401735-40-7
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: SRQLCVQQSGZFCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  8
• 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：

  Dimethyl 2-but-3-enyl-2-cyclohex-2-en-1-ylpropanedioate 在 (1,10-phenanthroline)methylchloropalladium(II) 、 platinum(IV) oxide 、 氢气 作用下， 以 1,2-二氯乙烷 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以14%的产率得到dimethyl (3S,3aR,7aR)-3-ethyl-2,3,3a,4,5,6,7,7a-octahydroindene-1,1-dicarboxylate
  参考文献：
  名称：

  Chain-Walking Strategy for Organic Synthesis: Catalytic Cycloisomerization of 1,n-Dienes

  摘要：

  The catalytic construction of carbon-carbon bonds in small organic molecules via chain walking is described. Catalytic cycloisomerization of 1,n-dienes via chain walking was achieved using a palladium-1,10-phenanthroline catalyst to form five-membered-ring products. By means of a cycloisomerization/hydrogenation protocol, 1,7- to 1,14-dienes were selectively converted to bicyclo[4.3.0]nonane derivatives. The use of chain walking provides a new method in organic synthesis to functionalize unreactive carbon-hydrogen bonds by letting the catalyst look for preferable bond-forming sites by moving around on the substrate.

  DOI：

  10.1021/ja308377u
• 作为产物：
  描述：

  丙二酸二甲酯 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 Dimethyl 2-but-3-enyl-2-cyclohex-2-en-1-ylpropanedioate
  参考文献：
  名称：

  Chain-Walking Strategy for Organic Synthesis: Catalytic Cycloisomerization of 1,n-Dienes

  摘要：

  The catalytic construction of carbon-carbon bonds in small organic molecules via chain walking is described. Catalytic cycloisomerization of 1,n-dienes via chain walking was achieved using a palladium-1,10-phenanthroline catalyst to form five-membered-ring products. By means of a cycloisomerization/hydrogenation protocol, 1,7- to 1,14-dienes were selectively converted to bicyclo[4.3.0]nonane derivatives. The use of chain walking provides a new method in organic synthesis to functionalize unreactive carbon-hydrogen bonds by letting the catalyst look for preferable bond-forming sites by moving around on the substrate.

  DOI：

  10.1021/ja308377u

文献信息

• Chain Walking as a Strategy for Carbon–Carbon Bond Formation at Unreactive Sites in Organic Synthesis: Catalytic Cycloisomerization of Various 1,<i>n</i>-Dienes
  作者：Taro Hamasaki、Yuka Aoyama、Junichi Kawasaki、Fumitoshi Kakiuchi、Takuya Kochi

  DOI：10.1021/jacs.5b10804

  日期：2015.12.30

  via chain walking was achieved for the palladium-catalyzed cycloisomerization of 1,n-dienes. Various 1,n-dienes (n = 7-14) such as those containing cyclic alkenes, acyclic internal alkenes, and a trisubstituted alkene can be used for the chain-walking cycloisomerization/hydrogenation process, and five-membered ring compounds including simple cyclopentane and pyrrolidine derivatives can easily be prepared

  在钯催化的 1,n-二烯环异构化过程中，通过链式行走在有机小分子中的非反应性 sp(3)-碳上形成碳-碳键。各种1,n-二烯（n = 7-14），如含有环状烯烃、无环内烯烃和三取代烯烃的那些，可用于链式环异构化/加氢过程，以及包括简单环戊烷在内的五元环化合物和吡咯烷衍生物可以很容易地制备。还发现在环异构化中可能发生在叔碳上的链行走。二烯的连接体部分不必包含季中心，具有两个烯烃部分由叔碳或氮原子连接的二烯底物也可用作底物。发现使用含有硝酸银的硅胶柱色谱法可有效分离一些不加氢的环异构化产物。氘标记实验提供了直接证据，表明该反应是通过链式行走机制进行的。
• Chain-Walking Strategy for Organic Synthesis: Catalytic Cycloisomerization of 1,<i>n</i>-Dienes
  作者：Takuya Kochi、Taro Hamasaki、Yuka Aoyama、Junichi Kawasaki、Fumitoshi Kakiuchi

  DOI：10.1021/ja308377u

  日期：2012.10.10

  The catalytic construction of carbon-carbon bonds in small organic molecules via chain walking is described. Catalytic cycloisomerization of 1,n-dienes via chain walking was achieved using a palladium-1,10-phenanthroline catalyst to form five-membered-ring products. By means of a cycloisomerization/hydrogenation protocol, 1,7- to 1,14-dienes were selectively converted to bicyclo[4.3.0]nonane derivatives. The use of chain walking provides a new method in organic synthesis to functionalize unreactive carbon-hydrogen bonds by letting the catalyst look for preferable bond-forming sites by moving around on the substrate.