(S)-5-Phenylsulfanyl-pentan-2-ol | 162661-38-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (S)-5-Phenylsulfanyl-pentan-2-ol
• 英文别名: (s)-(+)-5-(Phenylthio)-2-pentanol；(2S)-5-phenylsulfanylpentan-2-ol
• CAS: 162661-38-3
• 化学式: C₁₁H₁₆OS
• 分子量: 196.313
• InChiKey: CYWJNXOXFOZDAD-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-5-Phenylsulfanyl-pentan-2-ol 生成 (2S,6R,8S)-(-)-2,8-dimethyl-1,7-dioxaspiro<5.5>undecane
  参考文献：
  名称：

  Applications of highly enantioenriched alcohols bearing a phenylthio group in the preparation of ring compounds. The two-pot synthesis of an enantiopure spiroacetal pheromone bearing three chiral centers

  摘要：

  The new chiron (S)-6-phenylthio-2-hexanol (3) was prepared in high enantiomeric excess by baker's yeast reduction of the corresponding ketone. Enantioenriched alcohols 1, 2 and 3, prepared previously by a similar procedure, or their racemic counterparts, were transformed into ring closed compounds 5-methyl-2-(phenylthio)tetrahydrofuran (9), 6-methyl-2-(phenylthio)tetrahydropyran (10), 2-methyl-1-phenylsulfonyl cyclopropane (14), cyclobutane (15), cyclopentane (16), and a bee pheromone, (2S,6R,8S)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane (20). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00635-2
• 作为产物：
  描述：

  5-(phenylthio)pentan-2-one 在 RuBr₂{(R)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl} 氢气 作用下， 以 甲醇 为溶剂， 80.0 ℃ 、11.5 MPa 条件下， 反应 70.0h， 生成 (S)-5-Phenylsulfanyl-pentan-2-ol 、 (R)-5-(Phenylthio)-2-pentanol
  参考文献：
  名称：

  手性Ru（II）催化剂对苯硫基酮的不对称加氢反应

  摘要：

  据报道，使用手性Ru（II）催化剂可对苯硫基酮进行不对称氢化。获得完全转化和对映体过量高达98％。©1997由Elsevier Science Ltd发布。

  DOI：

  10.1016/s0040-4039(97)00530-3

文献信息

• S-(+)-5-(Phenylthio)-2-pentanol and S-(+)-4-(Phenylthio)-2-butanol: Readily Prepared, Useful Additions to the Chirality Pool. Highly Enantioselective Syntheses of Naturally Occurring Spiroketal Pheromones
  作者：Hong Liu、Theodore Cohen

  DOI：10.1021/jo00112a025

  日期：1995.4

  The new chirons (S)-4-(phenylthio)-2-butanol (4) and (S)-5-(phenylthio)-2-pentanol (3) have been prepared efficiently in high enantiomeric excess by enzymatic reduction of the corresponding readily available ketones. Using the latter as a chiral building block, the highly optically enriched insect pheromonal components (5S,7S)-7-methyl-1,6-dioxaspiro[4.5]decane (7), (2S,6R)-2-methyl-1,7-dioxaspiro[5.5]undecane (8), and (2S,6R)-2-methyl-1,7-dioxaspiro[5.6]dodecane (9) have been synthesized in one pot by sequential deprotonation, reductive lithiation, transmetalation with cerium(III) chloride, treatment with lactones, and acidification.