S-tert-butyl-N-methyl-S-phenylsulfoximine | 200135-59-7

• 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: S-tert-butyl-N-methyl-S-phenylsulfoximine
• 英文别名: (+/-)-S-(tert-butyl)-N-methyl-S-phenylsulfoximine；Tert-butyl-methylimino-oxo-phenyl-lambda6-sulfane；tert-butyl-methylimino-oxo-phenyl-λ6-sulfane
• CAS: 200135-59-7
• 化学式: C₁₁H₁₇NOS
• 分子量: 211.328
• InChiKey: FQCYRYGAUJIDEU-UHFFFAOYSA-N

物化性质

• 沸点：
  305.0±25.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-tert-butyl-N-methyl-S-phenylsulfoximine 在 正丁基锂 、 碘 、 magnesium(II) perchlorate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 26.17h， 以80%的产率得到S-(2-iodophenyl)-N-methylbenzenesulfinamide
  参考文献：
  名称：

  ortho-Lithiation of S-tert-butyl-S-phenylsulfoximines. New route to enantiopure sulfinamides via a de-tert-butylation reaction

  摘要：

  The sulfoximine group proved to be an excellent ortho-directing group in lithiation reactions. Several electrophiles were used to afford the corresponding ortho-functionalized aryl sulfoximines in good yields. The use of prochiral electrophiles lead to modest to good diastereoselectivities up to 95%. During this study, we observed a side reaction due to a S-de-tert-butylation. After optimization of this S-de-tert-butylation reaction, the corresponding enantiopure sulfinamides could be obtained in good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.047
• 作为产物：
  描述：

  S-(tert-butyl)-S-phenylsulfoximine 、 碘甲烷 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 13.0h， 以86%的产率得到S-tert-butyl-N-methyl-S-phenylsulfoximine
  参考文献：
  名称：

  ortho-Lithiation of S-tert-butyl-S-phenylsulfoximines. New route to enantiopure sulfinamides via a de-tert-butylation reaction

  摘要：

  The sulfoximine group proved to be an excellent ortho-directing group in lithiation reactions. Several electrophiles were used to afford the corresponding ortho-functionalized aryl sulfoximines in good yields. The use of prochiral electrophiles lead to modest to good diastereoselectivities up to 95%. During this study, we observed a side reaction due to a S-de-tert-butylation. After optimization of this S-de-tert-butylation reaction, the corresponding enantiopure sulfinamides could be obtained in good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.047

文献信息

• Structure and reactivity of a sulfoximine-stabilized chiral dilithiocarbanion
  作者：Jürgen F. K. Müller、Markus Neuburger、Margareta Zehnder

  DOI：10.1002/hlca.19970800717

  日期：1997.11.3

  mixed tetrameric mono- and dilithio salt. Unexpectedly, a separation of the enantiomers in mono-and dilithiated antipodes with respect to the chirality center on the S-atom is observed. Dilithiation of S-ethyl-N-methyl-S-phenylsulfoximine (1) affords a chiral dinucleophile which undergoes highly regie- and stereoselective alkylation reactions with bis-electrophiles.

  提出了以N，N，N'，N'-四甲基乙烷-1,2-二胺（TMEDA）为配位溶剂的外消旋二锂化S-乙基-N-甲基-S-苯基亚砜肟簇2的合成及X射线分析。锂络合物2由混合的四聚单和二硫代盐组成。出乎意料的是，观察到相对于S原子上的手性中心，在单和双锂化对映体中对映体的分离。S-乙基-N-甲基-S-苯基亚砜亚胺的二甲酸酯化（1）得到手性二亲核试剂，其与双亲电子试剂进行高度的反应和立体选择性烷基化反应。