(R)-1-iodo-3-methylheptane | 1393538-43-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: (R)-1-iodo-3-methylheptane
• 英文别名: (3R)-1-iodo-3-methylheptane
• CAS: 1393538-43-6
• 化学式: C₈H₁₇I
• 分子量: 240.127
• InChiKey: VCSPDXXEILDYTM-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (R)-1-iodo-3-methylheptane 、 (R)-2-methyl-1-(4-methylphenylsulfonyl)decane 在 正丁基锂 、 甲基溴化镁 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 4.67h， 生成 (5R,9R)-5,9-dimethylheptadecane
  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：

  (S)-2-hexanol 在 咪唑 、 lithium aluminium tetrahydride 、 水 、 碘 、 三甲胺盐酸盐 、 sodium hydride 、 三乙胺 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 6.5h， 生成 (R)-1-iodo-3-methylheptane
  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