dimethyl (S)-2-(2-hexyl)malonate | 1393538-40-3

• 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: dimethyl (S)-2-(2-hexyl)malonate
• 英文别名: (S)-2-(1-methylpentyl)malonic acid dimethyl ester；dimethyl 2-[(2S)-hexan-2-yl]propanedioate
• CAS: 1393538-40-3
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: YUZLWQVNDSDIKM-QMMMGPOBSA-N

物化性质

• 沸点：
  237.8±8.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  15.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dimethyl (S)-2-(2-hexyl)malonate 在 水 、 lithium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 3.5h， 以82%的产率得到(S)-(-)-methyl 3-methylheptanoate
  参考文献：
  名称：

  Stereospecific inversion of secondary tosylates to yield chiral methyl-branched building blocks, applied to the asymmetric synthesis of leafminer sex pheromones

  摘要：

  All four of the possible stereoisomers of 5,9-dimethylheptadecane, the major sex pheromone component secreted by female moths of the mountain-ash bentwing (Leucoptera scitella), were synthesized by the coupling of two chiral blocks with a methyl branch at the 2- or 3-position. The blocks were prepared by applying the stereospecific inversion of secondary tosylates, which were derived from (R)- and (S)-propylene oxide, and their enantiopurities were confirmed by chiral HPLC analysis. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.023
• 作为产物：
  描述：

  (2R)-hexan-2-ol 在 三甲胺盐酸盐 、 sodium hydride 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 dimethyl (S)-2-(2-hexyl)malonate
  参考文献：
  名称：

  Stereospecific inversion of secondary tosylates to yield chiral methyl-branched building blocks, applied to the asymmetric synthesis of leafminer sex pheromones

  摘要：

  All four of the possible stereoisomers of 5,9-dimethylheptadecane, the major sex pheromone component secreted by female moths of the mountain-ash bentwing (Leucoptera scitella), were synthesized by the coupling of two chiral blocks with a methyl branch at the 2- or 3-position. The blocks were prepared by applying the stereospecific inversion of secondary tosylates, which were derived from (R)- and (S)-propylene oxide, and their enantiopurities were confirmed by chiral HPLC analysis. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.023