2-[(phenylsulfanyl)methyl]dodecanal | 808137-56-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[(phenylsulfanyl)methyl]dodecanal
• 英文别名: 2-(Phenylsulfanylmethyl)dodecanal
• CAS: 808137-56-6
• 化学式: C₁₉H₃₀OS
• 分子量: 306.513
• InChiKey: OKAZDDJRHREDMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Dimethylzinc 、 2-[(phenylsulfanyl)methyl]dodecanal 在 四氯化钛 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 3-[(phenylsulfanyl)methyl]tridecan-2-ol 、 3-[(phenylsulfanyl)methyl]tridecan-2-ol
  参考文献：
  名称：

  Diastereoselective addition of organozinc reagents to 2-alkyl-3-(arylsulfanyl)propanals

  摘要：

  The preparation of compounds incorporating the 3-hydroxy-2-methyl-1-alkyl moiety of high diastereomeric purity is described. Such compounds can serve as potential building blocks for the preparation of several kinds of natural products. Diastereoselective synthesis of two potential pine sawfly pheromone components, one the pure racemic threo-isomer of 3-methylpentadecan-2-ol and the other the racemic erythro-isomer of 3-methyltridecan-2-ol are described. The diastereoselective addition of R2Zn (R = Me, Et and n-Bu) to several 2-alkyl-3-(arylsulfanyl)propanals in the presence of a Lewis acid and CH2Cl2 as solvent was studied. An excellent diastereomeric ratio (95/5 anti-Cram/Cram) was obtained with 2-[(phenylsulfanyl)methyl]pentanal, 2-[(phenylsulfanyl)methyl]decanal and 2-[(phenylsulfanyl)methyl]dodecanal and Me2Zn in the presence of TiCl4. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.005
• 作为产物：
  描述：

  十二醛 在 聚合甲醛 、 二乙胺盐酸盐 、 三乙胺 作用下， 以 水 为溶剂， 反应 12.0h， 生成 2-[(phenylsulfanyl)methyl]dodecanal
  参考文献：
  名称：

  Diastereoselective addition of organozinc reagents to 2-alkyl-3-(arylsulfanyl)propanals

  摘要：

  The preparation of compounds incorporating the 3-hydroxy-2-methyl-1-alkyl moiety of high diastereomeric purity is described. Such compounds can serve as potential building blocks for the preparation of several kinds of natural products. Diastereoselective synthesis of two potential pine sawfly pheromone components, one the pure racemic threo-isomer of 3-methylpentadecan-2-ol and the other the racemic erythro-isomer of 3-methyltridecan-2-ol are described. The diastereoselective addition of R2Zn (R = Me, Et and n-Bu) to several 2-alkyl-3-(arylsulfanyl)propanals in the presence of a Lewis acid and CH2Cl2 as solvent was studied. An excellent diastereomeric ratio (95/5 anti-Cram/Cram) was obtained with 2-[(phenylsulfanyl)methyl]pentanal, 2-[(phenylsulfanyl)methyl]decanal and 2-[(phenylsulfanyl)methyl]dodecanal and Me2Zn in the presence of TiCl4. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.005

文献信息

• Diastereoselective addition of organozinc reagents to 2-alkyl-3-(arylsulfanyl)propanals
  作者：Michael Larsson、Elodie Galandrin、Hans-Erik Högberg

  DOI：10.1016/j.tet.2004.09.005

  日期：2004.11

  The preparation of compounds incorporating the 3-hydroxy-2-methyl-1-alkyl moiety of high diastereomeric purity is described. Such compounds can serve as potential building blocks for the preparation of several kinds of natural products. Diastereoselective synthesis of two potential pine sawfly pheromone components, one the pure racemic threo-isomer of 3-methylpentadecan-2-ol and the other the racemic erythro-isomer of 3-methyltridecan-2-ol are described. The diastereoselective addition of R2Zn (R = Me, Et and n-Bu) to several 2-alkyl-3-(arylsulfanyl)propanals in the presence of a Lewis acid and CH2Cl2 as solvent was studied. An excellent diastereomeric ratio (95/5 anti-Cram/Cram) was obtained with 2-[(phenylsulfanyl)methyl]pentanal, 2-[(phenylsulfanyl)methyl]decanal and 2-[(phenylsulfanyl)methyl]dodecanal and Me2Zn in the presence of TiCl4. (C) 2004 Elsevier Ltd. All rights reserved.