(3S,4R)-3-<2-(tert-butyloxy)-ethyl>-4-vinyl-5-pentanolide | 147589-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,4R)-3-<2-(tert-butyloxy)-ethyl>-4-vinyl-5-pentanolide
• CAS: 147589-69-3
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: ONVBNKZJUPLTAD-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-<2-(tert-butyloxy)-ethyl>-4-vinyl-5-pentanolide 在 重铬酸吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-[(4S,5R)-5-ethenyl-2-oxooxan-4-yl]acetaldehyde
  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：

  (3S,4R)-3-<2-(tert-butyloxy)-ethyl>-4-triphenylmethyloxymethyl-5-hexenal 在 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 生成 (3S,4R)-3-<2-(tert-butyloxy)-ethyl>-4-vinyl-5-pentanolide 、 (3R,4R)-3-<2-(tert-butyloxy)-ethyl>-4-vinyl-5-pentanolide 、 (3R,4S)-3-<2-(tert-butyloxy)-ethyl>-4-vinyl-5-pentanolide
  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

• 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).