(S)-(-)-ethyl-α-(para-tolylsufinyl) acetate | 150334-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(-)-ethyl-α-(para-tolylsufinyl) acetate
• 英文别名: ethyl 2-[(S)-(4-methylphenyl)sulfinyl]acetate
• CAS: 150334-46-6
• 化学式: C₁₁H₁₄O₃S
• 分子量: 226.296
• InChiKey: HMJPGZAQKXEQCN-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-2,2-二甲基-1,3-二氧戊环-4-乙醛 、 (S)-(-)-ethyl-α-(para-tolylsufinyl) acetate 在 叔丁基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Bakers' yeast oxidation of methyl para-tolylsuifide: Synthesis of a chiral intermediate in the preparation of the mevinic acid-type hypocholestemic agents

  摘要：

  The use of (R)-methyl para-tolylsulfoxide as a chiral auxiliary in a novel synthesis of a key intermediate en route to mevinic acid-type hypocholestemic agents is described. The synthesis is short and simple consisting of eight steps to yield enantiomerically pure beta-silyloxy-delta-lactone. The chiral sulfoxide used in the synthesis was obtained via a straightforward biooxidation of methyl paratolylsulfide using bakers' yeast (Saccharomyces cerevisiae NCYC 73). The biotransformation involves the use of whole cells and affords the sulfoxide in good yield and with high stereoselectivity.

  DOI：

  10.1016/0040-4020(95)00819-t
• 作为产物：
  描述：

  (S)-(-)-甲基对甲苯亚砜 、 氯甲酸乙酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 以95%的产率得到(S)-(-)-ethyl-α-(para-tolylsufinyl) acetate
  参考文献：
  名称：

  Bakers' yeast oxidation of methyl para-tolylsuifide: Synthesis of a chiral intermediate in the preparation of the mevinic acid-type hypocholestemic agents

  摘要：

  The use of (R)-methyl para-tolylsulfoxide as a chiral auxiliary in a novel synthesis of a key intermediate en route to mevinic acid-type hypocholestemic agents is described. The synthesis is short and simple consisting of eight steps to yield enantiomerically pure beta-silyloxy-delta-lactone. The chiral sulfoxide used in the synthesis was obtained via a straightforward biooxidation of methyl paratolylsulfide using bakers' yeast (Saccharomyces cerevisiae NCYC 73). The biotransformation involves the use of whole cells and affords the sulfoxide in good yield and with high stereoselectivity.

  DOI：

  10.1016/0040-4020(95)00819-t

文献信息

• The first highly asymmetric pummerer-type reaction in chiral acyclic sulfoxides: Chemistry of O-silylated ketene acetals
  作者：Yasuyuki Kita、Norio Shibata、Naoki Yoshida

  DOI：10.1016/s0040-4039(00)60616-0

  日期：1993.6

  The chiral sulfoxides (4) were reacted with O-silylated ketene acetal (2) in acetonitrile to give the corresponding α-siloxysulfides (5) in high degree of stereochemistry and high yields.

  使手性亚砜（4）与O-甲硅烷基化的乙烯酮缩醛（2）在乙腈中反应，以高立体化学度和高收率得到相应的α-甲硅烷氧基硫化物（5）。
• Kita, Yasuyuki; Shibata, Norio; Yoshida, Naoki, Journal of the Chemical Society. Perkin transactions I, 1994, # 22, p. 3335 - 3342
  作者：Kita, Yasuyuki、Shibata, Norio、Yoshida, Naoki、Fujita, Shigekazu

  DOI：——

  日期：——