Diethyl 2-cyclohex-2-en-1-yl-2-pent-4-enylpropanedioate | 1401735-43-0

• 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: Diethyl 2-cyclohex-2-en-1-yl-2-pent-4-enylpropanedioate
• 英文别名: diethyl 2-cyclohex-2-en-1-yl-2-pent-4-enylpropanedioate
• CAS: 1401735-43-0
• 化学式: C₁₈H₂₈O₄
• 分子量: 308.418
• InChiKey: SPZHGSVGOMYCSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  Diethyl 2-cyclohex-2-en-1-yl-2-pent-4-enylpropanedioate 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29%的产率得到diethyl (3S,3aR,7aR)-3-propyl-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：

  5-溴-1-戊烯 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 Diethyl 2-cyclohex-2-en-1-yl-2-pent-4-enylpropanedioate
  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

• Metal‐Catalyzed Sequential Formation of Distant Bonds in Organic Molecules: Palladium‐Catalyzed Hydrosilylation/Cyclization of 1, <i>n</i> ‐Dienes by Chain Walking
  作者：Takuya Kochi、Kazuya Ichinose、Masayuki Shigekane、Taro Hamasaki、Fumitoshi Kakiuchi

  DOI：10.1002/anie.201814558

  日期：2019.4.8

  Sequential formation of distant bonds in organic molecules was achieved for the palladium‐catalyzed hydrosilylation/cyclization of various 1,n‐dienes by chain walking of the metal catalyst. The reaction was applicable to various 1,n‐dienes, including a 1,13‐diene, to form a cyclopentane ring as well as a carbon–silicon bond at a remote site. The use of “nondissociative” chain walking provides a fascinating

  通过金属催化剂的链行走，钯催化的各种1，n-二烯的氢化硅烷化/环化反应实现了有机分子中远键的顺序形成。该反应适用于各种1，n-二烯，包括1,13-二烯，可在远端形成环戊烷环以及碳-硅键。“非解离”链走的使用为有机合成提供了一种引人入胜的策略，通过有效地将反应中心从较远位置移开，可以在催化循环内以特定顺序功能化有机分子的遥远部分。
• 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.