(Z)-1-hexylcyclooct-1-ene | 76182-97-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (Z)-1-hexylcyclooct-1-ene
• 英文别名: 1-hexylcyclooctene；(1Z)-1-hexylcyclooctene
• CAS: 76182-97-3
• 化学式: C₁₄H₂₆
• 分子量: 194.36
• InChiKey: ULGRSTSAMIDVOH-OWBHPGMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (Z)-1-hexylcyclooct-1-ene 在 对甲苯磺酸 六甲基磷酰三胺 、 sodium tetrahydroborate 、 溴 、 碳酸氢钠 、 臭氧 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 6.5h， 生成 2-(7-hydroxy-n-heptyl)-2-n-hexyl-1-3-dioxolane
  参考文献：
  名称：

  anhydromyriocin (anhydrothermozymocidin) 对映异构体的全合成

  摘要：

  anhydromyriocin 的光学对映体，即衍生自抗生素 myriocin (thermozymocidin) 的 γ-内酯，由 L-阿拉伯糖合成，确定 myriocin 的绝对构型为 47。与其天然对映异构体相比，它显示出很少的抗真菌活性。

  DOI：

  10.1139/v81-044
• 作为产物：
  描述：

  1-溴-1-环辛烯 、 己基溴化镁 在 C₃₂H₅₆Li₂NiO₄ 作用下， 以 四氢呋喃 、 甲基叔丁基醚 为溶剂， 反应 24.0h， 以63%的产率得到(Z)-1-hexylcyclooct-1-ene
  参考文献：
  名称：

  A Highly Reduced Ni–Li–Olefin Complex for Catalytic Kumada–Corriu Cross-Couplings

  摘要：

  The catalytic activity of a highly reduced Ni catalyst in the context of a Kumada-Corriu cross coupling has been studied. This nickel complex is characterized by its high electron density, stabilized by simple olefin ligands in combination with two Li ions. Landmark reactivity has been found with this precatalyst which operates at cryogenic temperatures, thus allowing the presence of sensitive functionalities. Structural elucidation of oxidative addition intermediates and their reactivity suggest highly reduced species being operative in the C-C bond forming event.

  DOI：

  10.1021/jacs.8b09849

文献信息

• The synthesis of the (−)-enantiomer of (+)-anhydromyriocin (), the γ-lactone derived from myriocin (thermozymocidin)
  作者：George Just、Daniel R. Payette

  DOI：10.1016/s0040-4039(00)78650-3

  日期：1980.1

  The optical antipode of the lactone derived from myriocin or thermozymocidin has been synthesized from L-arabinose.

  已经从L-阿拉伯糖合成了衍生自肉豆球菌素或热zymocidin的内酯的旋光对映体。
• Synthesis of the Antifungal Agent Neoenactin A and Its N-Deshydroxy Derivative
  作者：Ihab S. Darwish、Marvin J. Miller

  DOI：10.1021/jo00081a027

  日期：1994.1

  The first total and unequivocal syntheses of neoenactin A (1, NE A) as well as its N-deshydroxy analog 2 are described. The two key steps in the syntheses were the oxidative cleavage of an appropriate olefin 8a to yield the desired keto acid 9 and the Michael addition of serinehydroxamates 11 or 12 to the appropriate vinyl ketone 10. Biological activity of 1 and 2 against Escherichia coli and several fungi has been investigated.
• A Highly Reduced Ni–Li–Olefin Complex for Catalytic Kumada–Corriu Cross-Couplings
  作者：Lukas Nattmann、Sigrid Lutz、Pascal Ortsack、Richard Goddard、Josep Cornella

  DOI：10.1021/jacs.8b09849

  日期：2018.10.24

  The catalytic activity of a highly reduced Ni catalyst in the context of a Kumada-Corriu cross coupling has been studied. This nickel complex is characterized by its high electron density, stabilized by simple olefin ligands in combination with two Li ions. Landmark reactivity has been found with this precatalyst which operates at cryogenic temperatures, thus allowing the presence of sensitive functionalities. Structural elucidation of oxidative addition intermediates and their reactivity suggest highly reduced species being operative in the C-C bond forming event.
• A total synthesis of the enantiomer of anhydromyriocin (anhydrothermozymocidin)
  作者：Daniel R. Payette、George Just

  DOI：10.1139/v81-044

  日期：1981.1.15

  The optical antipode of anhydromyriocin, the γ-lactone derived from the antibiotic myriocin (thermozymocidin), was synthesized from L-arabinose, establishing the absolute configuration of myriocin as 47. In contrast to its natural enantiomer, it showed but little antifungal activity.

  anhydromyriocin 的光学对映体，即衍生自抗生素 myriocin (thermozymocidin) 的 γ-内酯，由 L-阿拉伯糖合成，确定 myriocin 的绝对构型为 47。与其天然对映异构体相比，它显示出很少的抗真菌活性。