Ditert-butyl 2-cyclohex-2-en-1-yl-2-pent-4-enylpropanedioate | 1401735-44-1

• 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: Ditert-butyl 2-cyclohex-2-en-1-yl-2-pent-4-enylpropanedioate
• 英文别名: ditert-butyl 2-cyclohex-2-en-1-yl-2-pent-4-enylpropanedioate
• CAS: 1401735-44-1
• 化学式: C₂₂H₃₆O₄
• 分子量: 364.525
• InChiKey: QSQUDBHXUKCYEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  Ditert-butyl 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， 反应 3.0h， 以23%的产率得到ditert-butyl (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：

  丙二酸二叔丁酯 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 Ditert-butyl 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

• 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.