(R)-(methylsulfanylmethyl)phenyl sulfoxide | 670271-24-6

• 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)-(methylsulfanylmethyl)phenyl sulfoxide
• 英文别名: [(R)-(Methylsulfanyl)methanesulfinyl]benzene；[(R)-methylsulfanylmethylsulfinyl]benzene
• CAS: 670271-24-6
• 化学式: C₈H₁₀OS₂
• 分子量: 186.299
• InChiKey: NRNZRQYQJQUCHA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-benzodithiole 1-oxide 在 [ReOCl₃(PPh₃)₂] sodium periodate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 (R)-(methylsulfanylmethyl)phenyl sulfoxide
  参考文献：
  名称：

  Dioxygenase-catalysed sulfoxidation of bicyclic alkylaryl sulfides and chemoenzymatic synthesis of acyclic disulfoxides

  摘要：

  Toluene- and naphthalene-dioxygenase-catalysed oxidation of six bicyclic disulfide substrates, using whole cells of Pseudomonas putida, gave the corresponding monosulfoxides with high ee values and enantiocomplementarity, in most cases. Two alcohol-sulfoxide diastereoisomers, formed from the reaction of the (R)-1,3-benzodithiole-1-oxide metabolite with n-butyllithium and benzaldehyde, were separated and stereochemically assigned. Treatment, of enantiopure (1R,3R)-benzo-1,3-dithiole-1,3-dioxide, obtained by chemoenzymatic synthesis, with alkyllithium reagents, resulted in a novel ring-opening reaction which proceeded with inversion of configuration to yield a series of acyclic disulfoxides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.107

文献信息

• Sulfoxides of high enantiopurity from bacterial dioxygenase-catalysed oxidation
  作者：Christopher C. R. Alien、Derek R. Boyd、Howard Dalton、Narain D. Sharma、Simon A. Haughey、R. Austin S. McMordie、Brian T. McMurray、Gary N. Sheldrake、Kenneth Sproule

  DOI：10.1039/c39950000119

  日期：——

  to effect dioxygenase-catalysed asymmetric cis-dihydroxylation of alkenes) have been found to yield chiral sulfoxides from the corresponding sulfides with a strong preference for the (R)- or (S)-configurations but without evidence of sulfone formation; similar results obtained using an Escherichia coli clone (pKST11, containing the Tod C1 C2 B and A genes encoding toluene dioxygenase from P. putida

  已发现恶臭假单胞菌的选定菌株（先前显示可实现烯烃的双加氧酶催化的不对称顺式-二羟基化反应）可从相应的硫化物中产生手性亚砜，强烈偏爱（R）-或（S）-构型，但没有砜形成的迹象；使用大肠杆菌克隆（pKST11，包含来自恶臭假单胞菌NCIMB 11767的编码甲苯双加氧酶的Tod C1 C2 B和A基因）获得的相似结果再次与立体选择性双加氧酶催化的硫氧化反应一致。