(R)-chloromethyl phenyl sulfoxide

• 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)-chloromethyl phenyl sulfoxide
• 英文别名: [(R)-chloromethylsulfinyl]benzene
• 化学式: C₇H₇ClOS
• 分子量: 174.651
• InChiKey: WCUSVVDFUIMPKY-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (-)-(R)-dichloromethyl phenyl sulfoxide 以84%的产率得到
  参考文献：
  名称：

  RAO, K. RAMA;BHANUMATHI, N.;SAMPATHKUMAR, H. M.;SATTUR, P. B., INDIAN J. CHEM. B, 29,(1990) N, C. 487

  摘要：

  DOI：

文献信息

• REACTION OF ALKYL ARYL SULFOXIDE WITH METHYL PHENYL<i>N</i>-CHLOROSULFOXIMIDE. DIRECT SYNTHESIS OF OPTICALLY ACTIVE α-CHLORO SULFOXIDE WITH OPTICALLY ACTIVE<i>N</i>-CHLOROSULFOXIMIDE
  作者：Hiroyuki Morita、Hideaki Itoh、Naomichi Furukawa、Shigeru Oae

  DOI：10.1246/cl.1978.817

  日期：1978.8.5

  Treatment of a few alkyl aryl sulfoxides with methyl phenyl N-chlorosulfoximide resulted in the quantitative formation of α-chloro sulfoxides. When the optically active methyl phenyl N-chlorosulfoximide was used, the α-chloro sulfoxides having optical activity on the sulfinyl sulfur were obtained from the corresponding sulfoxides.

  用甲基苯基 N-氯亚砜处理一些烷基芳基亚砜导致定量形成 α-氯亚砜。当使用旋光甲基苯基N-氯亚砜时，由相应的亚砜得到对亚磺酰硫具有旋光活性的α-氯亚砜。
• 4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB as an oxidative biocatalyst in the synthesis of optically active sulfoxides
  作者：Gonzalo de Gonzalo、Daniel E. Torres Pazmiño、Gianluca Ottolina、Marco W. Fraaije、Giacomo Carrea

  DOI：10.1016/j.tetasy.2005.11.024

  日期：2006.1

  sulfoxidation reactions on a set of aromatic sulfides. With a few exceptions, excellent enantioselectivities in the synthesis of chiral phenyl and benzyl sulfoxides were achieved. The bacterial Baeyer–Villiger monooxygenase was also shown to accept racemic sulfoxides, a prochiral diketone and an organoboron compound as substrates. This study demonstrates the great biocatalytic potential of this novel oxidative

  来自荧光假单胞菌ACB的重组4-羟基苯乙酮单加氧酶（HAPMO）已作为一组芳族硫化物的硫氧化反应的催化剂进行了测试。除少数例外，在手性苯基和苄基亚砜的合成中获得了极好的对映选择性。细菌Baeyer-Villiger单加氧酶也被证明可以接受外消旋亚砜，前手性二酮和有机硼化合物作为底物。这项研究证明了这种新型氧化酶的巨大生物催化潜力。
• Enzymatic Resolution and Decarboxylative Functionalization of α‐Sulfinyl Esters
  作者：Suraksha Gahalawat、Yesu Addepalli、Stephen P. Fink、Lakshmi Kasturi、Sanford D. Markowitz、Joseph M. Ready

  DOI：10.1002/chem.202302996

  日期：2024.2

  Enzymatic resolution of α-sulfinyl esters gives recovered ester and α-sulfinyl acid in high enantiomeric purity. Decarboxylative functionalization provides access to a wide range of optically active sulfoxides in both enantiomeric forms.

  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。
• On the nature of the chain-extending species in organolithium initiated stereospecific reagent-controlled homologation reactions using α-chloroalkyl aryl sulfoxides
  作者：Amanda L. Hoyt、Paul R. Blakemore

  DOI：10.1016/j.tetlet.2014.08.123

  日期：2015.6

  The reaction of an organolithium with an alpha-chloroalkyl aryl sulfoxide ostensibly generates an alpha-chloroalkyllithium by sulfoxide lithium exchange, but the actual identity of the chain-extending species in chlorosulfoxide-based StReCH reactions is not certain. To explore this issue, racemic 2-cyclohexyl (4R*, 5R*)-4,5-diphenyl-1,3,2-dioxaborolane was homologated by treatment with scalemic (S)-chloromethyl phenyl sulfoxide and n-BuLi (THF, -78 degrees C). The reaction proceeded without a detectable level of kinetic resolution, a finding consistent with chloromethyllithium being the active chain-extending species rather than a chiral sulfurane intermediate. (C) 2014 Elsevier Ltd. All rights reserved.
• MORITA H.; ITOH H.; FURUKAWA N.; OAE S., CHEM. LETT., 1978, NO 8, 817-820
  作者：MORITA H.、 ITOH H.、 FURUKAWA N.、 OAE S.

  DOI：——

  日期：——