2-hydroxy-2-methyl-3-phenylsulfenyl-3,4,6-heptatriene | 154227-27-7

• 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-hydroxy-2-methyl-3-phenylsulfenyl-3,4,6-heptatriene
• CAS: 154227-27-7
• 化学式: C₁₄H₁₆OS
• 分子量: 232.346
• InChiKey: OEWHIHMVTWDKDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2-methyl-3-phenylsulfenyl-3,4,6-heptatriene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.33h， 以45%的产率得到2,2-dimethyl-3-phenylsulfenyl-4-bromo-5-ethenyl-2,5-dihydrofuran
  参考文献：
  名称：

  Lithiation of 1-phenylsulfenyl-4-penten-1-ynes and reactions with electrophiles

  摘要：

  1-Phenylsulfeny-4-penten-1-yne 1a, upon treatment with n-butyllithium, gave 2a that could be trapped with H2O, D2O and MeI leading regioselectively to the allene derivatives 3, 4 and 5 respectively. Also regioselective was the reaction of 2a with ketones furnishing very high yields of the allenic alcohols 6, 7 and 8. Similarly regioselective was the coupling of 2b with acetone affording allenic alcohol 18. Less regioselective were the reactions with aldehydes, leading to mixtures of allenic and propargylic alchools. Allenic alcohols 8 and 18 can be cyclized to dihydrofurans 19 and 20.

  DOI：

  10.1016/s0040-4020(01)80568-8
• 作为产物：
  描述：

  magnesium,ethynylsulfanylbenzene,bromide 在 正丁基锂 、 1,2-双(二苯基膦)乙烷氯化镍 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 生成 2-hydroxy-2-methyl-3-phenylsulfenyl-3,4,6-heptatriene
  参考文献：
  名称：

  Lithiation of 1-phenylsulfenyl-4-penten-1-ynes and reactions with electrophiles

  摘要：

  1-Phenylsulfeny-4-penten-1-yne 1a, upon treatment with n-butyllithium, gave 2a that could be trapped with H2O, D2O and MeI leading regioselectively to the allene derivatives 3, 4 and 5 respectively. Also regioselective was the reaction of 2a with ketones furnishing very high yields of the allenic alcohols 6, 7 and 8. Similarly regioselective was the coupling of 2b with acetone affording allenic alcohol 18. Less regioselective were the reactions with aldehydes, leading to mixtures of allenic and propargylic alchools. Allenic alcohols 8 and 18 can be cyclized to dihydrofurans 19 and 20.

  DOI：

  10.1016/s0040-4020(01)80568-8

文献信息

• Lithiation of 1-phenylsulfenyl-4-penten-1-ynes and reactions with electrophiles
  作者：Saverio Florio、Ludovico Ronzini、Erbana Epifani、Riccardo Sgarra

  DOI：10.1016/s0040-4020(01)80568-8

  日期：1993.1

  1-Phenylsulfeny-4-penten-1-yne 1a, upon treatment with n-butyllithium, gave 2a that could be trapped with H2O, D2O and MeI leading regioselectively to the allene derivatives 3, 4 and 5 respectively. Also regioselective was the reaction of 2a with ketones furnishing very high yields of the allenic alcohols 6, 7 and 8. Similarly regioselective was the coupling of 2b with acetone affording allenic alcohol 18. Less regioselective were the reactions with aldehydes, leading to mixtures of allenic and propargylic alchools. Allenic alcohols 8 and 18 can be cyclized to dihydrofurans 19 and 20.