2-Nonen-5-ol | 85355-76-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Nonen-5-ol
• 英文别名: 7-nonen-5-ol；Non-2-en-5-ol
• CAS: 85355-76-6；85355-77-7
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: YNAPJTXCVLTFDB-UHFFFAOYSA-N

物化性质

• 沸点：
  203.8±9.0 °C(Predicted)
• 密度：
  0.843±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2R*,3S*)-1-(Tosyloxy)-3-iodohexan-2-ol 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 2-Nonen-5-ol
  参考文献：
  名称：

  C-1 Reactivity of 2,3-Epoxy Alcohols via Oxirane Opening with Metal Halides: Applications and Synthesis of Naturally Occurring 2,3-Octanediol, Muricatacin, 3-Octanol, and 4-Dodecanolide

  摘要：

  The C-1 reactivity of 2,3-epoxy alcohols and derivatives has been examined thoroughly. In the first approach a rearrangement opening of 2,3-epoxy alcohols with LiI leads to 1-iodo 2,3-diols with erythro or three stereochemistry starting from trans or cis epoxy alcohols. Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been applied to the asymmetric synthesis of the naturally occurring (S,S)-2,3-octanediol and (R,R)-muricatacin. The second approach, starting from easily available tosyloxy epoxides, leads to the highly regioselective opening of the oxirane ring with Li halides. The 3-iodohydrins obtained can be reduced to the corresponding 1-(tosyloxy)alkan-2-ols and then coupled with common carbon nucleophiles to afford, in high yields, optically active alcohols. This methodology has been applied to the asymmetric synthesis of naturally occurring pheromones like 3(R)-octanol and 4(R)-dodecanolide.

  DOI：

  10.1021/jo00120a025

文献信息

• Regioreversed addition of crotylmagnesium chloride to carbonyl compounds in the presence of aluminum chloride
  作者：Yoshinori Yamamoto、Kazuhiro Maruyama

  DOI：10.1021/jo00157a046

  日期：1983.5