(R)-methyl 2-phenylsulfenylacetate | 98639-89-5

• 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 2-phenylsulfenylacetate
• 英文别名: methyl 2-[(R)-phenylsulfinyl]acetate
• CAS: 98639-89-5
• 化学式: C₉H₁₀O₃S
• 分子量: 198.243
• InChiKey: JPPXZUDQIXZLIL-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-phenylsulfenylacetate 在 N-氯代丁二酰亚胺 、 caesium carbonate 作用下， 生成 methyl (S)-2,2-dichloro-2-(phenylsulfinyl)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：

  2-苯基亚硫酰基乙酸甲酯 在 Corinebacterium equi 作用下， 反应 24.0h， 以43%的产率得到(R)-methyl 2-phenylsulfenylacetate
  参考文献：
  名称：

  ENZYME MEDIATED SYNTHESIS OF OPTICALLY ACTIVE ω-ARENESULFINYLALKANOIC ESTERS

  摘要：

  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。

  DOI：

  10.1246/cl.1986.217

文献信息

• Chemistry of oxaziridines. 17. N-(Phenylsulfonyl)(3,3-dichlorocamphoryl)oxaziridine: a highly efficient reagent for the asymmetric oxidation of sulfides to sulfoxides
  作者：Franklin A. Davis、R. Thimma Reddy、Wei Han、Patrick J. Carroll

  DOI：10.1021/ja00030a045

  日期：1992.2

  The synthesis, structure, and enantioselective oxidations of a new chiral N-sulfonyloxaziridine 12c [3,3-dichloro- 1,7,7-trimethyl-2'-(phenylsulfonyl)spiro[bicyclo[2.2.1]heptane-2,3'-oxaziridine]] are reported. This oxidant, which exhibits remarkably high and predictable ee's for the enantioselective oxidation of prochiral sulfides to sulfoxides, is prepared in three steps from (+)- or (-)-camphor

  一种新型手性 N-磺酰氧氮丙啶 12c [3,3-二氯-1,7,7-三甲基-2'-(苯基磺酰基)螺[双环[2.2.1]庚烷-2,3]的合成、结构和对映选择性氧化'-oxaziridine]] 报道。这种氧化剂在将前手性硫化物对映选择性氧化成亚砜方面表现出非常高且可预测的 ee，它是由 (+)- 或 (-)-樟脑以 50% 的总产率通过三个步骤制备的
• A facile route to homochiral sulfoxides
  作者：Kevin Burgess、Ian Henderson

  DOI：10.1016/s0040-4039(01)80467-6

  日期：1989.1

  Biocatalytic resolutions of methyl sulfinylacetates fford sulfoxides (R)-(1) - (6) in very high optical yields; the products have been used in a systematic study of the “SPAC” reaction, an asymmetric synthesis of γ-hydroxy-α,β-unsaturated esters.

  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。
• Electrochemical enzymatic deoxygenation of chiral sulfoxides utilizing DMSO reductase
  作者：Mitsuru Abo、Makiko Dejima、Fumioki Asano、Akira Okubo、Sunao Yamazaki

  DOI：10.1016/s0957-4166(00)00004-5

  日期：2000.2

  Preparation of enantiomerically enriched sulfoxides by an electrochemical enzymatic system utilizing DMSO reductase was studied. This system consists of a glassy carbon electrode as the working electrode, methyl viologen as the mediator and DMSO reductase from Rhodobacter sphaeroides f. sp. denitrificans as the catalyst. The (R)-enantiomers of chiral sulfoxides in the presence of a variety of functional

  研究了利用DMSO还原酶的电化学酶系统制备对映体富集的亚砜的方法。该系统由玻璃状碳电极作为工作电极，甲基紫精作为介体和球形红球菌f的DMSO还原酶组成。sp。脱硝酶作为催化剂。通过该系统以高ee（＞ 97％）获得在多种官能团存在下的手性亚砜的（R）-对映异构体。
• (-)-.alpha.,.alpha.-Dichlorocamphorsulfonyloxaziridine: a superior reagent for the asymmetric oxidation of sulfides to sulfoxides
  作者：Franklin A. Davis、R. ThimmaReddy、Michael C. Weismiller

  DOI：10.1021/ja00197a080

  日期：1989.7
• 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).