(S,3Z)-2-(2-butynyloxy)-3-hexene | 136185-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S,3Z)-2-(2-butynyloxy)-3-hexene
• 英文别名: (Z,2S)-2-but-2-ynoxyhex-3-ene
• CAS: 136185-45-0
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: MPSOEMIHDFCXMZ-ZEBCKKTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S,3Z)-2-(2-butynyloxy)-3-hexene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以75%的产率得到(4R,5S,6E)-5-ethyl-6-octen-2-yn-4-ol
  参考文献：
  名称：

  通过阴离子氧基-Cope重排进行非环状非对映控制和不对称传递。（+）-呋喃醛和（-）-鸟氨酸的关键前体的合成

  摘要：

  The anionic oxy-Cope rearrangements of acyclic 1,5-dien-3-ols, when their stereochemistries are properly designated. are shown to proceed with a high level of diastereoselection and asymmetric transmission. The utility of the acyclic oxy-Cope variants is demonstrated by the stereocontrolled synthesis of the key precursors of (+)-faranal (insect pheromone) and (-)-antirhine (Corynanthe-type indole alkaloid).

  DOI：

  10.1016/s0040-4020(01)86283-9
• 作为产物：
  描述：

  ethyl (S)-2-(2-butynyloxy)propionate 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 正己烷 为溶剂， 反应 6.5h， 生成 (S,3Z)-2-(2-butynyloxy)-3-hexene
  参考文献：
  名称：

  通过阴离子氧基-Cope重排进行非环状非对映控制和不对称传递。（+）-呋喃醛和（-）-鸟氨酸的关键前体的合成

  摘要：

  The anionic oxy-Cope rearrangements of acyclic 1,5-dien-3-ols, when their stereochemistries are properly designated. are shown to proceed with a high level of diastereoselection and asymmetric transmission. The utility of the acyclic oxy-Cope variants is demonstrated by the stereocontrolled synthesis of the key precursors of (+)-faranal (insect pheromone) and (-)-antirhine (Corynanthe-type indole alkaloid).

  DOI：

  10.1016/s0040-4020(01)86283-9

文献信息

• SMALL MOLECULE COMPOUNDS SELECTIVE AGAINST GRAM-NEGATIVE BACTERIAL INFECTIONS
  申请人：DeBrabander Jef

  公开号：US20150329582A1

  公开（公告）日：2015-11-19

  The described invention provides fully synthetic, biologically active mangrolide A. It describes schemes to chemically synthesize mangrolide A, intermediates and analogs of mangrolide A, and their antibacterial activity.

  所描述的发明提供了完全合成的生物活性芒格酮A。它描述了化学合成芒格酮A、芒格酮A的中间体和类似物的方案，以及它们的抗菌活性。
• Acyclic diastereocontrol and asymmetric transmission via anionic oxy-Cope rearrangement: a synthetic application of sequential [2,3]Wittig-oxy-Cope rearrangements
  作者：Shih Yi Wei、Katsuhiko Tomooka、Takeshi Nakai

  DOI：10.1021/jo00021a002

  日期：1991.10

  The anionic oxy-Cope rearrangements of acyclic 1,5-dien-3-ols with the 3,4-erythro configuration established by the [2,3]Wittig rearrangement are shown to provide a useful level of diastereoselection and asymmetric transmission in the context of a formal asymmetric synthesis of an insect pheromone.
• Acyclic diastereocontrol and asymmetric transmission via anionic oxy-Cope rearrangement. Synthesis of key precursors of (+)-faranal and (−)-antirhine
  作者：Shih-Yi Wei、Katsuhiko Tomooka、Takeshi Nakai

  DOI：10.1016/s0040-4020(01)86283-9

  日期：1993.1

  The anionic oxy-Cope rearrangements of acyclic 1,5-dien-3-ols, when their stereochemistries are properly designated. are shown to proceed with a high level of diastereoselection and asymmetric transmission. The utility of the acyclic oxy-Cope variants is demonstrated by the stereocontrolled synthesis of the key precursors of (+)-faranal (insect pheromone) and (-)-antirhine (Corynanthe-type indole alkaloid).