2-(丁硫基)丙酸甲酯 | 71032-13-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-(丁硫基)丙酸甲酯
• 英文名称: methyl 2-(butylthio)propanoate
• 英文别名: Methyl-2-(butylthio)-propionat；Methyl 2-butylsulfanylpropanoate
• CAS: 71032-13-8
• 化学式: C₈H₁₆O₂S
• mdl: MFCD16040879
• 分子量: 176.28
• InChiKey: LGYNJCKAXHSHFR-UHFFFAOYSA-N

物化性质

• 沸点：
  218.5±23.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.875
• 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：

  2-(丁硫基)丙酸甲酯 在 N-氯代丁二酰亚胺 、 zinc(II) chloride 作用下， 以 四氯化碳 、 硝基甲烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl 3-(butylthio)-2,3-dihydro-3,6-dimethyl-2-oxobenzofuran-5-propanoate
  参考文献：
  名称：

  Kennedy, Michael; McKervey, M. Anthony; Maguire, Anita R., Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 1041 - 1045

  摘要：

  DOI：
• 作为产物：
  描述：

  甲醇 、 2-(butylthio)propanoyl chloride 以 二氯甲烷 为溶剂， 反应 0.17h， 以7.2 g的产率得到2-(丁硫基)丙酸甲酯
  参考文献：
  名称：

  Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates

  摘要：

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.009

文献信息

• Investigation of the reaction of α-thioamides, α-esters and α-nitriles with N-halosuccinimides
  作者：Marie Kissane、Maureen Murphy、Denis Lynch、Alan Ford、Anita R. Maguire

  DOI：10.1016/j.tet.2008.05.026

  日期：2008.8

  Investigation of the reaction of α-thioamides, α-esters and α-nitriles with NBS and NCS is described. The scope of this stereoselective oxidative transformation to the β-haloacrylamides, β-acrylates and β-acrylonitriles has been determined. A mechanistic rationale to explain the observed differences in reactivity between the amide, ester and nitrile series is proposed.

  描述了α-硫代酰胺，α-酯和α-腈与NBS和NCS的反应的研究。已经确定了这种立体选择性氧化转化为β-卤代丙烯酰胺，β-丙烯酸酯和β-丙烯腈的范围。提出了一种机械原理来解释所观察到的酰胺，酯和腈系列之间的反应性差异。
• Conformational effects on the 2,3-sigmatropic shift of sulfur-stabilized ylides and enolates involving bicyclic transition states
  作者：Edwin Vedejs、Michael J. Arnost、James P. Hagen

  DOI：10.1021/jo01332a029

  日期：1979.8
• KENNEDY, MICHAEL;MCKERVEY, M. ANTHONY;MAGUIRE, ANITA R.;NAUGHTON, SEAN, J. CHEM. SOC. PT 1. PERKIN TRANS.,(1990) N, C. 1041-1045
  作者：KENNEDY, MICHAEL、MCKERVEY, M. ANTHONY、MAGUIRE, ANITA R.、NAUGHTON, SEAN

  DOI：——

  日期：——
• Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates
  作者：Surrinder Koul、Jawahir Lal Koul、Budh Singh、Munish Kapoor、Rajinder Parshad、Kuldeep S. Manhas、Subhash C. Taneja、Ghulam N. Qazi

  DOI：10.1016/j.tetasy.2005.07.009

  日期：2005.8

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.
• Kennedy, Michael; McKervey, M. Anthony; Maguire, Anita R., Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 1041 - 1045
  作者：Kennedy, Michael、McKervey, M. Anthony、Maguire, Anita R.、Naughton, Sean

  DOI：——

  日期：——