(+)-(R)-Ethyl p-Methoxyphenyl Sulfoxide | 128092-50-2

• 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)-Ethyl p-Methoxyphenyl Sulfoxide
• 英文别名: ethyl (4-methoxyphenyl) sulfoxide；1-[(R)-ethylsulfinyl]-4-methoxybenzene
• CAS: 128092-50-2
• 化学式: C₉H₁₂O₂S
• 分子量: 184.259
• InChiKey: ZXOCKOZUJSEXPX-GFCCVEGCSA-N

物化性质

• 沸点：
  324.3±25.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+)-(S)-Ethyl(p-methoxyphenyl)methylsulfonium Perchlorate 在 过苯甲酸钠 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 (+)-(R)-Ethyl p-Methoxyphenyl Sulfoxide
  参考文献：
  名称：

  Takeuchi, Hiroyuki; Minato, Hiroshi; Kobayashi, Michio, Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 47, # 1 + 2, p. 165 - 172

  摘要：

  DOI：

文献信息

• Asymmetric Sulfinylations of<i>N</i>-Methylephedrine-Modified Tri- or Tetraalkyl Zincates by Symmetric Diaryl Sulfoxides
  作者：Simon Ruppenthal、Reinhard Brückner

  DOI：10.1002/ejoc.201701603

  日期：2018.6.7

  Diethylzinc was treated with 1 or 2 equiv. of AlkMgCl or PhMgBr (preferably) or with 1 equiv. of nBuLi (less efficiently) for forming species – plausibly zincates – which were sulfinylated by diaryl sulfoxides to give racemic alkyl aryl sulfoxides in yields reaching 100 %. Dialkylzinc reagents were also activated by treatments with 1 or 2 equiv. of an enantiomerically pure alkylmagnesium β‐aminoalkoxide

  二乙基锌用1或2当量处理。最好是AlkMgCl或PhMgBr或1当量的AlkMgCl或PhMgBr。的Ñ振振有词锌酸盐- -丁基锂（效率较低），用于形成物种这是由二芳基sulfinylated亚砜，得到外消旋烷基芳基亚砜中的产率达到100％。二烷基锌试剂也可以通过用1或2当量的处理来活化。对映体纯的烷基镁β-氨基醇盐。当醇盐来自二烷基镁试剂和等摩尔量的N-甲基-（-）-麻黄碱时，这种方法最有效。该第二活化模式允许用二芳基亚砜将本来是二烷基锌试剂的亚磺酰基化。这样生成对映体比例高达93：7的烷基芳基亚砜，产率高达100％。
• A General and Expeditious One-Pot Synthesis of Sulfoxides in High Optical Purity from Norephedrine-Derived Sulfamidites
  作者：José L. García Ruano、Carlos Alemparte、M. Teresa Aranda、María M. Zarzuelo

  DOI：10.1021/ol027232i

  日期：2003.1.1

  A general and simple procedure for preparing any kind of enantiomerically enriched sulfoxide starting from norephedrine-derived N-benzyloxycarbonylsulfamidite 3a is reported. After one-pot reaction of 3a with RMgX, HBF(4), and R'MgX, a variety of sulfoxides 6 are obtained in ee usually higher than 93% and isolated yields ranging between 50 and 78%. The obtained configuration is tunable by simply electing

  报道了一种从降麻黄碱衍生的N-苄氧基羰基亚磺酰胺3a开始制备任何种类的对映体富集的亚砜的通用且简单的方法。3a与RMgX，HBF（4）和R'MgX进行一锅反应后，在ee中获得的多种亚砜6通常高于93％，分离出的产率在50％至78％之间。通过简单地选择试剂的添加顺序就可以调整获得的配置。[反应-见文字]
• Symmetric Diarylsulfoxides as Asymmetric Sulfinylating Reagents for Dialkylmagnesium Compounds
  作者：Simon Ruppenthal、Reinhard Brückner

  DOI：10.1021/jo502417j

  日期：2015.1.16

  dilithium salt of (S)-BINOL was added as a promotor. Alkyl aryl sulfoxides resulted in up to quantitative yield and with up to 97% ee. This demonstrates the feasibility of asymmetric sulfinylations by achiral sulfinylating agents (from the perspective of Alkyl2Mg) as well as the feasibility of asymmetric sulfoxide–magnesium exchanges (from the perspective of Ar2SO).

  在-78°C下，当添加1.5当量的（S）-BINOL二锂盐作为促进剂时，伯二烷基镁化合物与二芳基亚砜反应。烷基芳基亚砜导致定量产率最高，ee高达97％。这证明了通过非手性亚磺化剂进行不对称亚磺酰基化的可行性（从烷基2 Mg的角度来看），以及不对称亚砜与镁交换的可行性（从Ar 2 SO角度来看）。
• Hydrogenative Kinetic Resolution of Vinyl Sulfoxides
  作者：Joan R. Lao、Héctor Fernández-Pérez、Anton Vidal-Ferran

  DOI：10.1021/acs.orglett.5b02139

  日期：2015.8.21

  Enantiopure sulfoxides are valuable precursors of organosulfur compounds with broad application in organic and pharmaceutical chemistry. An unprecedented strategy for obtaining highly enantioenriched sulfoxides based on a hydrogenative kinetic resolution using Rh-complexes of phosphine-phosphite ligands as catalysts is reported. After optimization, highly efficient conditions for the kinetic resolution of racemic sulfoxides have been identified. This methodology has been applied to a set of racemic aralkyl or aryl vinyl sulfoxides and allowed the isolation of both recovered and reduced products in excellent yields and enantioselectivities (up to 99% and 97% ee, respectively; 16 examples).