3-<(Dibenzylmethyl)thio>propan-1-ol | 133885-07-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-<(Dibenzylmethyl)thio>propan-1-ol
• 英文别名: 3-(1,3-Diphenylpropan-2-ylsulfanyl)propan-1-ol
• CAS: 133885-07-1
• 化学式: C₁₈H₂₂OS
• 分子量: 286.438
• InChiKey: SGQXYBVCMHBBON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2-Dibenzyl-1,3-thioxane 在 三氟甲磺酸三甲基硅酯 、 dimethyl sulfide borane 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到3-<(Dibenzylmethyl)thio>propan-1-ol
  参考文献：
  名称：

  Reduction of activated ketals with borane-dimethyl sulphide

  摘要：

  Borane-Dimethyl sulphide reduces ketals activated with TMSOTf at -78-degrees-C in dichloromethane. The scope and selectivity of the reagent has been investigated.

  DOI：

  10.1016/s0040-4039(00)74497-2

文献信息

• Reduction of activated ketals with borane-dimethyl sulphide
  作者：Roger Hunter、Birgit Bartels、Joseph P. Michael

  DOI：10.1016/s0040-4039(00)74497-2

  日期：1991.2

  Borane-Dimethyl sulphide reduces ketals activated with TMSOTf at -78-degrees-C in dichloromethane. The scope and selectivity of the reagent has been investigated.
• Bartels Birgit, Hunter Roger, J. Org. Chem, 58 (1993) N 24, S 6756-6765
  作者：Bartels Birgit, Hunter Roger

  DOI：——

  日期：——
• A selectivity study of activated ketal reduction with borane dimethyl sulfide
  作者：Birgit Bartels、Roger Hunter

  DOI：10.1021/jo00076a041

  日期：1993.11

  A chemo- and regioselectivity study of the reagent combination BH3.SMe2/TMSOTf for ketal reduction has been undertaken. It has revealed that simple 1,3-dioxanes reduce cleanly at low temperature in CH2Cl2 while simple 1,3-dioxolanes may give complete ring cleavage and dimerization products. A study of reduction of 4-substituted 1,3-dioxolanes has revealed a solvent-directed regioselectivity which in THF favors the secondary protected derivative. A mechanism is postulated to account for the selectivities based on recent thinking on acetal substitution reactions.