(E)-4-ethylhex-4-en-1-yl 4-methylbenzenesulfonate | 1122478-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-ethylhex-4-en-1-yl 4-methylbenzenesulfonate
• 英文别名: (E)-4-ethylhex-4-enyl 4-methylbenzenesulfonate；[(E)-4-ethylhex-4-enyl] 4-methylbenzenesulfonate
• CAS: 1122478-42-5
• 化学式: C₁₅H₂₂O₃S
• 分子量: 282.404
• InChiKey: JRYJKJUWAZVPPD-LNKIKWGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-ethylhex-4-en-1-yl 4-methylbenzenesulfonate 、 5-氰基-1H-吡咯-2-羧酸甲酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 以43%的产率得到(E)-methyl 5-cyano-1-(4-ethylhex-4-en-1-yl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis of rhazinilam through intramolecular arylcyanation of alkenes catalyzed cooperatively by nickel/aluminum

  摘要：

  Intramolecular arylcyanation across a tri-substituted double bond proceeds to give a primary alkyl cyanide product through functionalization of C-CN and allylic C-H bonds and double C-C bond formation in a 1,3-manner by cooperative nickel/AlMe2Cl catalysis. The transformation is applied to the synthesis of rhazinilam, a tubulin-binding alkaloid containing unique structural motifs such as axially chiral biaryl and strained nine-membered lactam as well as quaternary carbon. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.03.012
• 作为产物：
  描述：

  (E)-4-ethylhex-4-en-1-ol 、 对甲苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(E)-4-ethylhex-4-en-1-yl 4-methylbenzenesulfonate
  参考文献：
  名称：

  使用新型钯催化环化的（±）-鼠李素的全合成

  摘要：

  简明扼要的合成（±）鼠李，取决于新的氧化Heck环化和钯催化的直接偶联。描述了N -MOM-鼠李糖苷的X射线结构，其提供了对应变的9元内酰胺环的构象的洞察力。

  DOI：

  10.1021/jo801791j

文献信息

• Total Synthesis of (±)-Rhazinal Using Novel Palladium-Catalyzed Cyclizations
  作者：Alfred L. Bowie、Dirk Trauner

  DOI：10.1021/jo801791j

  日期：2009.2.20

  A concise synthesis of (±)-rhazinal that hinges on novel oxidative Heck cyclizations and palladium-catalyzed direct couplings is described. An X-ray structure of N-MOM-rhazinal, which provides insight into the conformation of the strained 9-membered lactam ring, is described.

  简明扼要的合成（±）鼠李，取决于新的氧化Heck环化和钯催化的直接偶联。描述了N -MOM-鼠李糖苷的X射线结构，其提供了对应变的9元内酰胺环的构象的洞察力。
• Synthesis of rhazinilam through intramolecular arylcyanation of alkenes catalyzed cooperatively by nickel/aluminum
  作者：Yuuya Yamada、Shiro Ebata、Tamejiro Hiyama、Yoshiaki Nakao

  DOI：10.1016/j.tet.2015.03.012

  日期：2015.7

  Intramolecular arylcyanation across a tri-substituted double bond proceeds to give a primary alkyl cyanide product through functionalization of C-CN and allylic C-H bonds and double C-C bond formation in a 1,3-manner by cooperative nickel/AlMe2Cl catalysis. The transformation is applied to the synthesis of rhazinilam, a tubulin-binding alkaloid containing unique structural motifs such as axially chiral biaryl and strained nine-membered lactam as well as quaternary carbon. (C) 2015 Elsevier Ltd. All rights reserved.