(+)-(R)-n-butyl tert-butyl sulfoxide | 126494-92-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: (+)-(R)-n-butyl tert-butyl sulfoxide
• 英文别名: (R)-tert-butyl butylsulfoxide；1-[(R)-tert-butylsulfinyl]butane
• CAS: 126494-92-6
• 化学式: C₈H₁₈OS
• 分子量: 162.296
• InChiKey: DGBVQXCCEZOOKY-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  正丁基锂 、 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以99%的产率得到(+)-(R)-n-butyl tert-butyl sulfoxide
  参考文献：
  名称：

  一种手性叔丁基亚砜的有效途径

  摘要：

  通过与各种有机金属反应，（S）-1,1-二苯基丙烷-1,2-二醇1的环状亚硫酸盐2得到具有高区域选择性和立体选择性的手性亚磺酸盐3或4。然后通过加入第二种有机金属试剂，以几乎定量的产率将手性亚磺酸盐转化为对映体纯的亚砜。

  DOI：

  10.1016/s0040-4039(01)80475-5

文献信息

• Stereoselective synthesis of isoindolinones and tert -butyl sulfoxides
  作者：Robert Kawęcki、Wojciech Stańczyk、Agnieszka Jaglińska

  DOI：10.1016/j.tet.2017.12.035

  日期：2018.2

  A reaction of Grignard reagents with an optically pure N-sulfinylimine derived from methyl 2-formylbenzoate yields enantioenriched isoindolinones and tert-butyl sulfoxides. The products are formed by the addition of the nucleophile to N-sulfinylimine followed by cyclization to form N-tert-butylsulfinylisoindolinone, which readily undergoes substitution with a second equivalent of Grignard reagent.

  格氏试剂与衍生自2-甲酰基苯甲酸甲酯的光学纯的N-亚磺酰亚胺反应，得到对映体富集的异吲哚啉酮和叔丁基亚砜。该产品通过加入亲核试剂，以形成Ñ -sulfinylimine随后环化，以形成ñ -叔-butylsulfinylisoindolinone，这容易经历取代与格氏试剂的第二等效。该反应可以在二氯甲烷中在室温或升高的温度下进行，而没有任何立体选择性的损失。还研究了格氏试剂以外的亲核试剂的使用。
• A general route to enantiomerically pure sulfoxides from a chiral sulfite
  作者：F. Rebiere、O. Samuel、L. Ricard、H. B. Kagan

  DOI：10.1021/jo00021a008

  日期：1991.10

  Enantiomerically pure cyclic chiral sulfite (S)-7 (trans stereochemistry) has been easily obtained in two steps from (S)-ethyl lactate. This compound was found to react cleanly with many organometallics to give crystalline sulfinates with high regioselectivity (> 90:10). Addition of a second organometallic transforms the purified sulfinate in excellent yield into a chiral sulfoxide (100% ee) of predictable absolute configuration. The mechanism and scope of this approach are discussed. This method completes the various other methods of preparation of chiral sulfoxides and is especially convenient for the preparation of tert-butyl sulfoxides. Examples for the synthesis of many chiral tert-butyl sulfoxides are given. The case of chiral sulfites derived from a C2 diol or of a chiral monoalcohol is also proposed as a route to chiral sulfinates, and some promising preliminary results have been obtained. The general main routes to obtain chiral sulfoxides from sulfites are also discussed.
• REBIERE, F.;KAGAN, H. B., TETRAHEDRON LETT., 30,(1989) N8, C. 3659-3662
  作者：REBIERE, F.、KAGAN, H. B.

  DOI：——

  日期：——