(±)-1-(phenylthio)butan-2-yl acetate | 139193-51-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (±)-1-(phenylthio)butan-2-yl acetate
• 英文别名: 2-Acetoxy-1-phenylthiobutane；1-Phenylsulfanylbutan-2-yl acetate
• CAS: 139193-51-4
• 化学式: C₁₂H₁₆O₂S
• 分子量: 224.324
• InChiKey: LCEQDZILNLBSJX-UHFFFAOYSA-N

物化性质

• 沸点：
  315.9±25.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-1-(phenylthio)butan-2-yl acetate 在 N-氯代丁二酰亚胺 、 zinc dibromide 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 [(3S,4S)-7,7-dimethyl-6-oxo-4-phenylsulfanyloctan-3-yl] acetate
  参考文献：
  名称：

  甲硅烷基烯醇醚与氯硫化物反应中的高非对映选择性

  摘要：

  氯硫化物1或2在无水溴化锌的存在下与甲硅烷基烯醇醚反应，分别主要得到相应的合成产物4或6。这些反应的高顺式选择性可以通过向螯合的手性巯基离子的亲核加成来解释。

  DOI：

  10.1016/s0040-4020(01)96197-6
• 作为产物：
  描述：

  苯硫酚 在 potassium carbonate 作用下， 以 水 为溶剂， 生成 (±)-1-(phenylthio)butan-2-yl acetate
  参考文献：
  名称：

  Highly enantioselective kinetic resolution of trans-2-(phenylthio)cyclohexanol derivatives by immobilized Candida antartica B lipase

  摘要：

  Candida antartica B (immobilized CAL-B) mediated resolutions of trans-2-(phenylthio)cyclohexanol derivatives using vinyl acetate as acylating agent and MTBE as solvent provide excellent enantioselectivity (up to >99%) and high yield of both the enantiomers in short reaction time. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.06.006

文献信息

• A facile chemoenzymatic route to enantiomerically pure oxiranes: building blocks for biologically active compounds
  作者：Ulrich Goergens、Manfred P. Schneider

  DOI：10.1039/c39910001064

  日期：——

  The enantiomerically pure building blocks (R)-and (S)-1–4 were prepared both by enantioselective, enzymatic hydrolysis and by acyl transfer, and subsequently converted into the corresponding enantiomerically pure oxiranes (R)- and (S)-7 and 8.

  对映体纯积木（[R ）-和（小号） - 1 - 4通过对映体选择性，酶水解和通过酰基转移制备两者，并随后转化为相应的对映体纯的环氧乙烷（[R ） -和（小号） - 7和8。
• Cobalt(II) chloride catalyzed acylation of alcohols with acetic anhydride: scope and mechanism
  作者：Javed Iqbal、Rajiv Ranjan Srivastava

  DOI：10.1021/jo00033a020

  日期：1992.3

  Cobalt(II) chloride catalyzes the acetylation of a variety of alcohols with acetic anhydride in excellent yield. Primary hydroxyl groups can be selectively acylated in the presence of secondary and tertiary ones while the secondary hydroxyl groups can be preferentially acetylated in the presence of tertiary ones. Tertiary alcohols have been found to give ketones, acetoacetates, olefins, and diketene in addition to the acetate. The beta-hydroxy esters and ketones can be acylated under these conditions without any elimination, and this reaction has been compared with 4-(dimethylamino)pyridine (DMAP)-mediated acylations where elimination of the resulting beta-acetoxy carbonyl compound is observed. A detailed investigation of the acylation of tertiary alcohols has revealed that these reactions proceed via a tertiary alkoxy radical and ketene. A mechanism for these acylations is proposed by invoking an electron-transfer process.