(+/-)-4,4-dimethyl-2H-tetrahydrothiopyran-2-acetic acid | 139376-95-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: (+/-)-4,4-dimethyl-2H-tetrahydrothiopyran-2-acetic acid
• 英文别名: 2-(4,4-Dimethylthian-2-yl)acetic acid
• CAS: 139376-95-7
• 化学式: C₉H₁₆O₂S
• 分子量: 188.291
• InChiKey: ODHKPLLJDFHROJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-溴-4,4-二甲基己-1-烯 在 氢氧化钾 、 二甲基硫 、 臭氧 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 36.0h， 生成 (+/-)-4,4-dimethyl-2H-tetrahydrothiopyran-2-acetic acid
  参考文献：
  名称：

  Tandem SN2-Michael reactions for the preparation of simple five- and six-membered-ring nitrogen and sulfur heterocycles

  摘要：

  A one-pot tandem S(N)2-Michael addition sequence has been developed for the preparation of five-membered- and six-membered-ring nitrogen and sulfur heterocycles from 6- or 7-halo-2-alkenoate esters. Nitrogen-containing rings are prepared by reaction of the omega-halo-2-alkenoate ester with a primary amine in the presence of triethylamine. The sulfur analogues are generated by thiourea displacement of the halide followed by base hydrolysis of the isothiouronium salt. Yields are routinely in the 60-80% range. Experiments are described which elucidate the chronology of the reaction sequences. Ring size and steric hindrance to the initial substitution reaction appear to be the only limitations of the procedure.

  DOI：

  10.1021/jo00032a025

文献信息

• Tandem SN2-Michael reactions for the preparation of simple five- and six-membered-ring nitrogen and sulfur heterocycles
  作者：Richard A. Bunce、Christopher J. Peeples、Paul B. Jones

  DOI：10.1021/jo00032a025

  日期：1992.3

  A one-pot tandem S(N)2-Michael addition sequence has been developed for the preparation of five-membered- and six-membered-ring nitrogen and sulfur heterocycles from 6- or 7-halo-2-alkenoate esters. Nitrogen-containing rings are prepared by reaction of the omega-halo-2-alkenoate ester with a primary amine in the presence of triethylamine. The sulfur analogues are generated by thiourea displacement of the halide followed by base hydrolysis of the isothiouronium salt. Yields are routinely in the 60-80% range. Experiments are described which elucidate the chronology of the reaction sequences. Ring size and steric hindrance to the initial substitution reaction appear to be the only limitations of the procedure.