2-benzylsulfanyl-propionyl chloride | 6182-84-9

• 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: 2-benzylsulfanyl-propionyl chloride
• 英文别名: 2-Benzylmercapto-propionylchlorid；2-Benzylsulfanylpropanoyl chloride
• CAS: 6182-84-9
• 化学式: C₁₀H₁₁ClOS
• 分子量: 214.716
• InChiKey: IYLZTRHFBLRIJC-UHFFFAOYSA-N

物化性质

• 沸点：
  138-139 °C(Press: 7-8 Torr)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-benzylsulfanyl-propionyl chloride 在 Trichosporon beigelli esterase 作用下， 以 phosphate buffer 、 二氯甲烷 为溶剂， 反应 12.17h， 生成 (R)-2-(benzylthio)propanoic acid
  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
• 作为产物：
  描述：

  2-（苄硫基）丙酸| 在 氯化亚砜 作用下， 生成 2-benzylsulfanyl-propionyl chloride
  参考文献：
  名称：

  羰基和一个α硫原子之间的相互作用。第一部分。一些α-（烷硫基）硫酯的红外和紫外光谱

  摘要：

  与未取代的硫代酯相比，某些α-（烷硫基）硫代酯表现出羰基拉伸频率向较低频率的偏移，并且在约500nm处具有强大的紫外线吸收最大值。285nm，未取代的硫代酯的光谱中没有。讨论了α-（烷硫基）-酮和-酯的光谱数据的相似性。

  DOI：

  10.1039/j29710000565

文献信息

• Thiol compounds. II. Synthesis and antihypertensive activity of mercaptoacylamino acids.
  作者：MASAYUKI OYA、JUNZOH MATSUMOTO、HIDEO TAKASHINA、TOSHIO WATANABE、JUNICHI IWAO

  DOI：10.1248/cpb.29.940

  日期：——

  The synthesis and structure-activity relationship of a series of mercaptoacylamino acids are described. These compounds were tested for antihypertensive activity. When the compounds were screened as angiotensin I-converting enzyme inhibitors in vitro, N-(2-mercaptopropanoyl)-L-cysteine-a (7a) and N2-(2-mercaptopropanoyl)-L-tryptophan-a (20a) were found to be 10 and 20 times more active than tiopronin, respectively.

  本文描述了一系列巯基氨基酸的合成和结构-活性关系。对这些化合物进行了抗高血压活性测试。在将这些化合物作为血管紧张素 I 转换酶抑制剂进行体外筛选时，发现 N-（2-巯基丙酰基）-L-半胱氨酸-a（7a）和 N2-（2-巯基丙酰基）-L-色氨酸-a（20a）的活性分别是硫普罗宁的 10 倍和 20 倍。
• Interaction between the carbonyl group and an α-sulphur atom. Part I. Infrared and ultraviolet spectra of some α-(alkylthio)thioesters
  作者：B. Wladislaw、H. Viertler、E. Berthold Demant

  DOI：10.1039/j29710000565

  日期：——

  Some α-(alkylthio)thioesters exhibit a shift of the carbonyl stretching frequency to lower frequencies in comparison with the unsubstituted thioesters, and a strong u.v. absorption maximum at ca. 285 nm, which is absent from the spectra of the unsubstituted thioesters. The similarity of the spectroscopic data for the α-(alkylthio)-ketones and -esters is discussed.

  与未取代的硫代酯相比，某些α-（烷硫基）硫代酯表现出羰基拉伸频率向较低频率的偏移，并且在约500nm处具有强大的紫外线吸收最大值。285nm，未取代的硫代酯的光谱中没有。讨论了α-（烷硫基）-酮和-酯的光谱数据的相似性。
• Mori, Yuji; Fujiwara, Shigeru; Miyachi, Toshiko, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 5, p. 1505 - 1517
  作者：Mori, Yuji、Fujiwara, Shigeru、Miyachi, Toshiko、Kitanishi, Hiroyuki、Oya, Masayuki、et al.

  DOI：——

  日期：——
• Cagniant; Cagniant, Bulletin de la Societe Chimique de France, 1959, p. 1998,2009
  作者：Cagniant、Cagniant

  DOI：——

  日期：——
• Dynamic Enzymatic Resolution of Thioesters
  作者：Pil-Je Um、Dale G. Drueckhammer

  DOI：10.1021/ja980445b

  日期：1998.6.1

  A detailed investigation of several issues related to the enzymatic resolution of thioesters under conditions of continuous racemization of substrate was conducted. The kinetic acidity of the alpha-protons of a series of alpha-substituted propionate thioesters was studied. It was found that the rate of alpha-proton exchange could be enhanced as much as 20-fold by variation of the thiol moiety, increasing the range of compounds to which enzymatic dynamic resolution may be applied. The relative rates of hydrolysis of ethyl butyrate and ethyl thiobutyrate by several enzymes commonly used in enzymatic resolution were determined. All of the enzymes studied exhibited similar rates of thioester and oxoester hydrolysis except for the esterase from pig liver, which showed very low activity in thioester hydrolysis. Dynamic resolution of the propargyl and trifluoroethyl thioesters of alpha-phenylpropionate was conducted using subtilisin Carlsberg as a catalyst. These examples demonstrated that enzymatic dynamic resolution can be applied even when the rate of alpha-proton exchange and the enantioselectivity of the enzyme are fairly low. A dynamic enzymatic transesterification procedure was demonstrated in the resolution of the trifluoroethyl thioester of alpha-(2,4-dichlorophenoxy)propionate, and product was obtained in 93% ee. This work helps expand and define the scope of enzymatic dynamic resolution of thioesters.