2-methylene-7-oxo-heptanoic acid methyl ester | 940279-16-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-methylene-7-oxo-heptanoic acid methyl ester
• 英文别名: Methyl 2-methylidene-7-oxoheptanoate；methyl 2-methylidene-7-oxoheptanoate
• CAS: 940279-16-3
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: LQAQWBBWZVNRJT-UHFFFAOYSA-N

物化性质

• 沸点：
  243.9±23.0 °C(predicted)
• 密度：
  0.985±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methylene-7-oxo-heptanoic acid methyl ester 在 四氯化钛 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以73%的产率得到(+/-)-(1R,2R)-2-hydroxy-1-iodomethyl-cyclohexanecarboxylic acid methyl ester
  参考文献：
  名称：

  Highly Diastereoselective Synthesis of vicinal Quaternary and Tertiary Stereocenters Using the Iodo-aldol Cyclization

  摘要：

  The intramolecular iodo-aldol cyclization of alpha-substituted enoate aldehydes and ketones is described. Using prochiral starting materials, the reaction produces hetero- and carbocycles containing quaternary centers adjacent to secondary or tertiary centers. The reactions occur in good yields and are highly selective for the trans-products, having the hydroxyl and iodomethyl groups on opposite faces of the ring system.

  DOI：

  10.1021/ol070482k
• 作为产物：
  描述：

  7,7-dimethoxy-2-methylene-heptanal 在 盐酸 、 sodium hydroxide 、 silver nitrate 、 溶剂黄146 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 4.0h， 生成 2-methylene-7-oxo-heptanoic acid methyl ester
  参考文献：
  名称：

  Highly Diastereoselective Synthesis of vicinal Quaternary and Tertiary Stereocenters Using the Iodo-aldol Cyclization

  摘要：

  The intramolecular iodo-aldol cyclization of alpha-substituted enoate aldehydes and ketones is described. Using prochiral starting materials, the reaction produces hetero- and carbocycles containing quaternary centers adjacent to secondary or tertiary centers. The reactions occur in good yields and are highly selective for the trans-products, having the hydroxyl and iodomethyl groups on opposite faces of the ring system.

  DOI：

  10.1021/ol070482k

文献信息

• Highly Diastereoselective Synthesis of <i>vicinal</i> Quaternary and Tertiary Stereocenters Using the Iodo-aldol Cyclization
  作者：Frederic Douelle、Amy S. Capes、Michael F. Greaney

  DOI：10.1021/ol070482k

  日期：2007.5.1

  The intramolecular iodo-aldol cyclization of alpha-substituted enoate aldehydes and ketones is described. Using prochiral starting materials, the reaction produces hetero- and carbocycles containing quaternary centers adjacent to secondary or tertiary centers. The reactions occur in good yields and are highly selective for the trans-products, having the hydroxyl and iodomethyl groups on opposite faces of the ring system.