(R)-(+)-Methyl <(4-chlorophenyl)sulfinyl>acetate | 102340-69-2

• 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: (R)-(+)-Methyl <(4-chlorophenyl)sulfinyl>acetate
• 英文别名: <((R)-4-Chlorophenyl)sulfinyl>acetate；methyl (R)-4-chlorophenylsulfinylacetate；(R)-(+)-Methyl [(4-chlorophenyl)sulfinyl]acetate；[((R)-4-Chlorophenyl)sulfinyl]acetate；methyl 2-[(R)-(4-chlorophenyl)sulfinyl]acetate
• CAS: 102340-69-2
• 化学式: C₉H₉ClO₃S
• 分子量: 232.688
• InChiKey: UTSGICRRSYOVEP-CQSZACIVSA-N

物化性质

• 熔点：
  63-65 °C(Solv: hexane (110-54-3); ethanol (64-17-5))
• 沸点：
  373.5±27.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-(+)-Methyl <(4-chlorophenyl)sulfinyl>acetate 在 N-氯代丁二酰亚胺 、 caesium carbonate 作用下， 生成 methyl (S)-2,2-dichloro-2-((4-chlorophenyl)sulfinyl)acetate
  参考文献：
  名称：

  α-亚磺酰酯的酶促分离和脱羧官能团化

  摘要：

  α-亚爷酯的酶促分离得到具有高对映体纯度的回收酯和 α-亚爷酸。脱羧官能团化提供了两种对映体形式的多种光学活性亚砜。

  DOI：

  10.1002/chem.202302996
• 作为产物：
  描述：

  环己基巯基乙酸甲酯 在 水 、 双氧水 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 96.0h， 生成 (R)-(+)-Methyl <(4-chlorophenyl)sulfinyl>acetate
  参考文献：
  名称：

  制备手性亚砜的简便方法

  摘要：

  以非常高的光学收率得到亚甲基乙酸乙酸甲酯和亚砜（R）-（1）-（6）的生物催化拆分；该产品已用于系统研究“ SPAC”反应，即不对称合成γ-羟基-α，β-不饱和酯。

  DOI：

  10.1016/s0040-4039(01)80467-6

文献信息

• ENZYME MEDIATED SYNTHESIS OF OPTICALLY ACTIVE ω-ARENESULFINYLALKANOIC ESTERS
  作者：Hiromichi Ohta、Yasuo Kato、Gen-ichi Tsuchihashi

  DOI：10.1246/cl.1986.217

  日期：1986.2.5

  Incubation of methyl arenesulfinylacetates and methyl α-benzenesulphinylpropionate with Corynebacterium equi IFO 3730 afforded the corresponding chiral sulfoxides of high optical purities in moderate to good chemical yields.

  将芳基亚磺酰基乙酸甲酯和α-苯亚磺酰基丙酸甲酯与马棒杆菌 IFO 3730 一起孵育，以中等至良好的化学产率提供了高光学纯度的相应手性亚砜。
• Asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids by Diels-Alder reaction
  作者：Carlos Cativiela、Pilar López、José A. Mayoral

  DOI：10.1016/s0957-4166(00)86334-x

  日期：1990.1
• Optically active building blocks from the SPAC reaction: a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone, a statine analog
  作者：Kevin Burgess、Juanita Cassidy、Ian Henderson

  DOI：10.1021/jo00006a017

  日期：1991.3

  Factors that govern chemical and optical yields of methyl gamma-hydroxy-alpha,beta-unsaturated esters 1 formed in reactions of optically active sulfinylacetates 2 with aldehydes (the ''SPAC'' reaction) are defined. Racemic samples of these chirons (1) can be resolved via acylations mediated by crude preparations of the lipase Pseudomonas K-10 in organic solvents. Combinations of asymmetric SPAC reactions with these biocatalytic resolutions provide routes to highly optically active esters 1 in good yields. This methodology is applied in a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone (15), a cyclic derivative of (3S,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (ACHPA).
• Continuous flow biocatalytic resolutions of methyl sulfinylacetates
  作者：Zhanxiang Liu、Kevin Burgess

  DOI：10.1016/j.tetlet.2011.09.024

  日期：2011.11

  Product inhibition was encountered for some substrates in the resolution of methyl sulfinylacetates mediated by lipase Amano AK, so an apparatus to continually extract the carboxylate product was devised. This was applied to resolve some sulfoxides with high enantiodifferentiation. (C) 2011 Published by Elsevier Ltd.
• Double diastereodifferentiation in the hydroxylative knovenagel condensation
  作者：Barry M. Trost、Sergio Mallart

  DOI：10.1016/s0040-4039(00)61441-7

  日期：1993.12

  The stereoinduction in formation of gamma-hydroxy-alpha,beta-unsaturated enoates using chiral alpha-sulfinyl esters and chiral aldehydes is a function of the absolute stereochemistry of the sulfoxide, the substituent on the sulfoxide, and the amount of base.