(S)-2-methyl-1-(4-methylphenylsulfonyl)decane | 1393538-47-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-methyl-1-(4-methylphenylsulfonyl)decane
• 英文别名: (S)-2-methyl-1-(p-tolylsulfonyl)decane；1-methyl-4-[(2S)-2-methyldecyl]sulfonylbenzene
• CAS: 1393538-47-0
• 化学式: C₁₈H₃₀O₂S
• 分子量: 310.501
• InChiKey: VHMGHAMEQUROLI-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-iodo-3-methylheptane 、 (S)-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,9S-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：

  1-溴代庚烷 在 正丁基锂 、 甲基溴化镁 、 三甲胺盐酸盐 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-2-methyl-1-(4-methylphenylsulfonyl)decane
  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

文献信息

• Stereospecific inversion of secondary tosylates to yield chiral methyl-branched building blocks, applied to the asymmetric synthesis of leafminer sex pheromones
  作者：Tomonori Taguri、Rei Yamakawa、Toru Fujii、Yuta Muraki、Tetsu Ando

  DOI：10.1016/j.tetasy.2012.05.023

  日期：2012.6

  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.