(S)-tert-butyl isobutyl sulfoxide | 13153-08-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: (S)-tert-butyl isobutyl sulfoxide
• 英文别名: (S)-1-(tert-Butylsulfinyl)-2-methylpropane；1-[(S)-tert-butylsulfinyl]-2-methylpropane
• CAS: 13153-08-7
• 化学式: C₈H₁₈OS
• 分子量: 162.296
• InChiKey: LPQJEAYNFGXMRS-JTQLQIEISA-N

物化性质

• 沸点：
  256.8±9.0 °C(Predicted)
• 密度：
  0.951±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl isobutyl sulfoxide 、 苯乙酮 在 lithium diisopropyl amide 作用下， 生成 (2R,3S)-4-Methyl-3-((S)-2-methyl-propane-2-sulfinyl)-2-phenyl-pentan-2-ol 、 (2S,3S)-4-Methyl-3-((S)-2-methyl-propane-2-sulfinyl)-2-phenyl-pentan-2-ol
  参考文献：
  名称：

  Stereoselective additions of sulphoxides carbonyl compounds

  摘要：

  The addition of the anions of primary alkyl p-tolyl sulphoxides to aldehydes gave mixtures of all four diastereoisomeric products with low selectivity under a variety of conditions. In contrast, additions of the corresponding t-butyl derivatives afforded just two isomers, with variable stereoselectivity.

  DOI：

  10.1016/s0040-4039(00)77693-3
• 作为产物：
  描述：

  quinine (R_S)-tert-butanesulfinate 、 Isobutylmagnesium chloride 以 四氢呋喃 、 乙醚 为溶剂， 以95%的产率得到(S)-tert-butyl isobutyl sulfoxide
  参考文献：
  名称：

  New General Sulfinylating Process for Asymmetric Synthesis of Enantiopure Sulfinates and Sulfoxides

  摘要：

  [GRAPHICS]A general process for the efficient synthesis of sulfinyl transfer agents has been developed using cinchona alkaloids quinine and quinidine as chiral auxiliaries. The importance of these new and unique sulfinyl transfer agents is exemplified by the expedient synthesis of several sulfoxides in excellent enantiopurities and high yields.

  DOI：

  10.1021/ol0501020

文献信息

• アミン立体異性体の製造方法
  申请人：アプシンターム・リミテッド・ライアビリティ・カンパニー

  公开号：JP2005522525A

  公开（公告）日：2005-07-28

  According to the present invention, a sulfinyl imine having an alcohol, thiol or amine residue on a sulfinyl group is stereoselectively reduced, or a sulfinyl imine stereoisomer having an alcohol, thiol or amine residue on a sulfinyl group is nucleophilic. Reacting with an atomic source to provide a sulfinylamine stereoisomer, and then contacting the sulfinylamine stereoisomer with a reagent suitable for cleavage of a sulfur-nitrogen bond to provide the amine stereoisomer. A method for producing amine stereoisomers is provided. The present invention also provides methods for using some of the above intermediates in the preparation of novel intermediates, sulfoxide and sulfinylamine stereoisomers useful in the above methods.

  根据本发明，对具有醇基、硫醇基或胺基残基的亚砜亚胺进行立体选择性还原，或者对具有醇基、硫醇基或胺基残基的亚砜亚胺立体异构体进行亲核反应。与原子源反应，提供亚砜胺立体异构体，然后将亚砜胺立体异构体与适用于裂解硫-氮键的试剂接触，以提供胺立体异构体。提供一种生产胺立体异构体的方法。本发明还提供了使用上述一些中间体在制备新型中间体、对上述方法有用的亚砜和亚砜胺立体异构体的方法。
• Practical and highly stereoselective technology for preparation of enantiopure sulfoxides and sulfinamides utilizing activated and functionally differentiated N-sulfonyl-1,2,3-oxathiazolidine-2-oxide derivatives
  作者：Zhengxu Han、Dhileepkumar Krishnamurthy、Paul Grover、Q. Kevin Fang、Xiping Su、H. Scott Wilkinson、Zhi-Hui Lu、Daniel Magiera、Chris H. Senanayake

  DOI：10.1016/j.tet.2005.03.122

  日期：2005.6

  A simple, general, and practical technology to prepare enantiopure 1,2,3-oxathiazolidine-2-oxide derivatives using chiral aryl N-sulfonyl aminoalcohol derivatives and thionyl chloride is reported. The versatility of these novel chiral building blocks (MIOO and TMPOO), was exemplified by the expedient production of a variety of unique chiral sulfoxides and valuable chiral sulfinamides in excellent yields

  报道了一种使用手性芳基N-磺酰基氨基醇衍生物和亚硫酰氯制备对映体纯的1,2,3-氧杂噻唑烷-2-氧化物衍生物的简单，通用和实用的技术。这些新颖的手性结构单元（MIOO和TMPOO）的多功能性，以简便的方法以优异的收率和对映体纯度生产了各种独特的手性亚砜和有价值的手性亚磺酰胺类产品。
• Methods of preparing sulfinamides and sulfoxides
  申请人：Senanayake Hugh Chris

  公开号：US20060128767A1

  公开（公告）日：2006-06-15

  This invention encompasses novel methods of preparing sulfinamides and sulfoxides, particularly stereomerically pure sulfinamides and sulfoxides. The invention further encompasses novel compounds from which sulfinamides and sulfoxides can be prepared.

  这项发明涵盖了制备磺酰胺和磺氧化物的新方法，特别是立体异构纯的磺酰胺和磺氧化物。该发明还涵盖了可以制备磺酰胺和磺氧化物的新化合物。
• Methods of Preparing Sulfinamides and Sulfoxides
  申请人：Senanayake Hugh Chris

  公开号：US20070293682A1

  公开（公告）日：2007-12-20

  This invention encompasses novel methods of preparing sulfinamides and sulfoxides, particularly stereomerically pure sulfinamides and sulfoxides. The invention further encompasses novel compounds from which sulfinamides and sulfoxides can be prepared.

  本发明涵盖了制备磺酰胺和磺醇的新方法，特别是立体异构纯的磺酰胺和磺醇。该发明还涵盖了可以制备磺酰胺和磺醇的新化合物。
• A Highly Selective and Practical Method for Enantiopure Sulfoxides Utilizing Activated and Functionally Differentiated N-Sulfonyl-1,2,3-oxathiazolidine-2-oxide Derivatives
  作者：Zhengxu Han、Dhileepkumar Krishnamurthy、Paul Grover、H. Scott Wilkinson、Q. Kevin Fang、Xiping Su、Zhi-Hui Lu、Daniel Magiera、Chris H. Senanayake

  DOI：10.1002/anie.200250644

  日期：2003.5.9