(2S)-phenyltetrahydro-2H-thiopyran | 1438891-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: (2S)-phenyltetrahydro-2H-thiopyran
• 英文别名: (2S)-2-phenylthiane
• CAS: 1438891-81-6
• 化学式: C₁₁H₁₄S
• mdl: MFCD00602701
• 分子量: 178.298
• InChiKey: CFZICUUBJLRTPM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-苯甲酰基丁酸甲酯 在 硼烷四氢呋喃络合物 、 sodiumsulfide nonahydrate 、 硼酸三甲酯 、 (S)-(+)-alpha,alpha-二苯基脯氨醇 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 38.0h， 生成 (2S)-phenyltetrahydro-2H-thiopyran 、 (2R)-phenyltetrahydro-2H-thiopyran
  参考文献：
  名称：

  Methods for the synthesis of chiral sulfur heterocycles and their application in the asymmetric Baylis–Hillman reactions

  摘要：

  Enantiomerically pure (2S,6S)-2,6-diphenyltetrahydro-2H-thiopyran, (2S)-2-phenyltetrahydro thiophene, and (2S)-2-phenyltetrahydro-2H-thiopyran were prepared in 70-72% yields and with 86-99% ee via cyclization of the corresponding dimesylate in an S(N)2 cyclization reaction using sodium sulfide nonahydrate. The results on the application of various chiral sulfides in asymmetric Baylis-Hillman reactions are also described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.021

文献信息

• Methods for the synthesis of chiral sulfur heterocycles and their application in the asymmetric Baylis–Hillman reactions
  作者：Mariappan Periasamy、Ramani Gurubrahamam、Gopal P. Muthukumaragopal

  DOI：10.1016/j.tetasy.2013.03.021

  日期：2013.5

  Enantiomerically pure (2S,6S)-2,6-diphenyltetrahydro-2H-thiopyran, (2S)-2-phenyltetrahydro thiophene, and (2S)-2-phenyltetrahydro-2H-thiopyran were prepared in 70-72% yields and with 86-99% ee via cyclization of the corresponding dimesylate in an S(N)2 cyclization reaction using sodium sulfide nonahydrate. The results on the application of various chiral sulfides in asymmetric Baylis-Hillman reactions are also described. (C) 2013 Elsevier Ltd. All rights reserved.