(R)-2-((S)-6-methylhept-5-en-2-yl)oxirane | 1350744-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (R)-2-((S)-6-methylhept-5-en-2-yl)oxirane
• 英文别名: (2R)-2-[(2S)-6-methylhept-5-en-2-yl]oxirane
• CAS: 1350744-21-6
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: GLYYRWADVSGYMW-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2-((S)-6-methylhept-5-en-2-yl)oxirane 在 氧气 、 copper(l) cyanide 、 臭氧 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.33h， 生成 (-)-cis-aerangis lactone
  参考文献：
  名称：

  A Formal, One-Pot β-Chlorination of Primary Alcohols and Its Utilization in the Transformation of Terpene Feedstock and the Synthesis of a C₂-Symmetrical Terminal Bis-Epoxide

  摘要：

  A one-pot transformation of alkan-1-ols into 2-chloroalkan-1-ols is described. As a practical application, terpene-derived primary alcohols were converted into semiochemicals such as olfactory lactones (aerangis lactone, whisky lactone, and cognac lactone) and pheromones (cruentol and ferrugineol). Using heptane-1,7-diol as a bifunctional substrate, the corresponding bis-epoxide was synthesized by bidirectional synthesis in good yield and high enantioselectivity.

  DOI：

  10.1021/jo402422b
• 作为产物：
  描述：

  (+)-香茅醛 在 N-氯代丁二酰亚胺 、 (2S,5R)‐2‐(tert‐butyl)‐3,5‐dimethylimidazolidin‐4‐one trifluoroacetate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 10.5h， 生成 (R)-2-((S)-6-methylhept-5-en-2-yl)oxirane 、 (S)-2-((S)-6-methylhept-5-en-2-yl)oxirane
  参考文献：
  名称：

  A Formal, One-Pot β-Chlorination of Primary Alcohols and Its Utilization in the Transformation of Terpene Feedstock and the Synthesis of a C₂-Symmetrical Terminal Bis-Epoxide

  摘要：

  A one-pot transformation of alkan-1-ols into 2-chloroalkan-1-ols is described. As a practical application, terpene-derived primary alcohols were converted into semiochemicals such as olfactory lactones (aerangis lactone, whisky lactone, and cognac lactone) and pheromones (cruentol and ferrugineol). Using heptane-1,7-diol as a bifunctional substrate, the corresponding bis-epoxide was synthesized by bidirectional synthesis in good yield and high enantioselectivity.

  DOI：

  10.1021/jo402422b

文献信息

• A Formal, One-Pot β-Chlorination of Primary Alcohols and Its Utilization in the Transformation of Terpene Feedstock and the Synthesis of a <i>C</i>₂-Symmetrical Terminal Bis-Epoxide
  作者：Jörg Swatschek、Lydia Grothues、Jonathan O. Bauer、Carsten Strohmann、Mathias Christmann

  DOI：10.1021/jo402422b

  日期：2014.2.7

  A one-pot transformation of alkan-1-ols into 2-chloroalkan-1-ols is described. As a practical application, terpene-derived primary alcohols were converted into semiochemicals such as olfactory lactones (aerangis lactone, whisky lactone, and cognac lactone) and pheromones (cruentol and ferrugineol). Using heptane-1,7-diol as a bifunctional substrate, the corresponding bis-epoxide was synthesized by bidirectional synthesis in good yield and high enantioselectivity.