(S)-2-(tert-butylsulfonyl)-propyl acetate | 179612-14-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: (S)-2-(tert-butylsulfonyl)-propyl acetate
• 英文别名: [(2S)-2-tert-butylsulfonylpropyl] acetate
• CAS: 179612-14-7
• 化学式: C₉H₁₈O₄S
• 分子量: 222.306
• InChiKey: IUADDGCKAVQBIS-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(tert-butylsulfonyl)-propyl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (2S)-2-tert-butylsulfonylpropan-1-ol
  参考文献：
  名称：

  Preparation of enantiomerically pure α-hydroxymethyl S-tert-Butyl sulfones by Candida antarctica lipase catalyzed resolution

  摘要：

  Candida antarctica lipase (CAL; Novozym 435) catalyzed acylation of racemic methyl and benzyl substituted hydroxy sulfones rac-3a and rac-3d, respectively, with vinyl acetate either neat or in ether solvents proceeded with E-values of 18 and 49. For the CAI, catalyzed hydrolysis of methyl substituted acetoxy sulfone rac-4a in an emulsion of phosphate buffer and methyl tert-butyl ether at pH 7.0 an E-value of 22 was found. Acetate (+)-emt-4a as well as alcohols (-)-3a and (-)-(S)-3d were obtained with ee-values of 99% on a gram scale. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00135-8
• 作为产物：
  描述：

  (+/-)-2-(tert-butylsulfonyl)-propyl acetate 生成 (S)-2-(tert-butylsulfonyl)-propyl acetate
  参考文献：
  名称：

  Preparation of enantiomerically pure α-hydroxymethyl S-tert-Butyl sulfones by Candida antarctica lipase catalyzed resolution

  摘要：

  Candida antarctica lipase (CAL; Novozym 435) catalyzed acylation of racemic methyl and benzyl substituted hydroxy sulfones rac-3a and rac-3d, respectively, with vinyl acetate either neat or in ether solvents proceeded with E-values of 18 and 49. For the CAI, catalyzed hydrolysis of methyl substituted acetoxy sulfone rac-4a in an emulsion of phosphate buffer and methyl tert-butyl ether at pH 7.0 an E-value of 22 was found. Acetate (+)-emt-4a as well as alcohols (-)-3a and (-)-(S)-3d were obtained with ee-values of 99% on a gram scale. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00135-8

文献信息

• Lipase catalyzed resolution of α-hydroxymethyl sulfones. Determination of absolute configuration by semiempirical calculation of CD spectra and verification by X-ray structure analysis
  作者：Hans-Joachim Gais、Ingo von der Weiden、Jörg Fleischhauer、Josef Esser、Gerhard Raabe

  DOI：10.1016/s0957-4166(97)00377-7

  日期：1997.9

  esterification of the methyl substituted alcohol and the benzyl substituted alcohol . The absolute configuration of and 1b was determined by measurement of their circular dichroism and the calculation of the CD spectra of 1a and 1b by semiempirical methods. The configurational assignment was verified by X-ray structure analysis of 1b and .

  的南极假丝酵母脂肪酶催化的羟甲基砜的酯化和导致的分离（92％ee）和图1b（≥99％ee）的，分别。该酰氧甲基砜（ee≥99％）是由南极假丝酵母脂肪酶催化水解得到的。在甲基取代的醇和苄基取代的醇的酯化反应中，不仅南极念珠菌脂肪酶，洋葱假单胞菌脂肪酶也显示出相反的对映体分化。和1b的绝对配置通过测量它们的圆二色性和通过半经验方法计算1a和1b的CD光谱来确定。通过1b和的X射线结构分析验证了构型分配。