(S)-N-tosyl-S-phenyl-S-(1-cyclohex-1-enylmethyl)sulfoximine | 102817-19-6

• 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: (S)-N-tosyl-S-phenyl-S-(1-cyclohex-1-enylmethyl)sulfoximine
• 英文别名: N-(cyclohexen-1-ylmethyl-oxo-phenyl-lambda6-sulfanylidene)-4-methylbenzenesulfonamide；N-(cyclohexen-1-ylmethyl-oxo-phenyl-λ6-sulfanylidene)-4-methylbenzenesulfonamide
• CAS: 102817-19-6
• 化学式: C₂₀H₂₃NO₃S₂
• 分子量: 389.54
• InChiKey: ABYLAULLSBECFF-VWLOTQADSA-N

物化性质

• 沸点：
  548.4±53.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-N-tosyl-S-phenyl-S-(1-cyclohex-1-enylmethyl)sulfoximine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 N-((S)-1-Cyclohex-1-enyl-ethyl)-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  手性烯丙基亚砜亚胺的非对映选择性反应和重排

  摘要：

  摘要：描述了手性烯丙基亚磺胺及其烷基亚砜亚胺对应物的亲核和亲电化学，包括高度官能化的环丙烷衍生物的合成。还描述了通过钯 (0) 催化的烯丙基亚砜亚胺重排为烯丙基亚磺酰胺的伯和仲 N-甲苯磺酰基烯丙基胺的合成。

  DOI：

  10.1080/10426509708545524
• 作为产物：
  描述：

  (+)-(S_S)-S-methyl-S-phenyl-N-(p-tolylsulphonyl)sulphoximine 在 正丁基锂 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 反应 3.67h， 生成 (S)-N-tosyl-S-phenyl-S-(1-cyclohex-1-enylmethyl)sulfoximine
  参考文献：
  名称：

  Palladium-Catalyzed Rearrangement of Allylic Sulfoximines:  Application to the Asymmetric Synthesis of Chiral Allylic Amines

  摘要：

  The palladium(0)-catalyzed reactions of the primary and secondary allylic sulfoximines 7, 9, 11, 13, 15, 17, and 19 gives allylic sulfinamides without 1,3-allylic rearrangement. These compounds were not isolated but were converted to their corresponding N-tosyl allylic amines, primary and secondary 8, 10, 12, 14, 16, 18, and 20, respectively. In the case of the optically active secondary allylic sulfoximines 17 and 19, chiral N-tosyl allylic secondary amines were formed in high enantiomeric purities.

  DOI：

  10.1021/jo9605105

文献信息

• Stereoselective synthesis of enantiomerically pure 1-(E)-alkenylsulfoximines
  作者：Irene Erdelmeier、Hans-Joachim Gais

  DOI：10.1016/s0040-4039(00)98734-3

  日期：1985.1

  Optically active (E)-N-tosyl-S-(1-alkenyl)-S-phenylsulfoximines 4 are synthesized stereoselectively in a one pot sequence from readily available 1 via C-silylation, metallation and reaction of the corresponding lithiosulfoximine 3 with various carbonyl compounds. The El-MS spectra of the so prepared alkenylsulfoximines 4 show unexpected fragmentations, pointing to a new, unusual S-O-migration of the

  旋光性（E）-N-甲苯磺酰基-S-（1-链烯基）-S-苯基亚磺酰亚胺亚胺4通过C-硅烷化，金属化和相应的硫代亚砜亚胺3与各种羰基的反应，从一个容易获得的1立体立体合成一锅顺序合成。化合物。如此制备的烯基亚砜肟基4的El-MS光谱显示出意想不到的断裂，表明1-烯基部分的新的，不寻常的SO-迁移。
• ERDELMEIER, I.;GAIS, H. -J., TETRAHEDRON LETT., 1985, 26, N 36, 4359-4362
  作者：ERDELMEIER, I.、GAIS, H. -J.

  DOI：——

  日期：——
• Palladium-Catalyzed Rearrangement of Allylic Sulfoximines:  Application to the Asymmetric Synthesis of Chiral Allylic Amines
  作者：Stephen G. Pyne、Zemin Dong

  DOI：10.1021/jo9605105

  日期：1996.1.1

  The palladium(0)-catalyzed reactions of the primary and secondary allylic sulfoximines 7, 9, 11, 13, 15, 17, and 19 gives allylic sulfinamides without 1,3-allylic rearrangement. These compounds were not isolated but were converted to their corresponding N-tosyl allylic amines, primary and secondary 8, 10, 12, 14, 16, 18, and 20, respectively. In the case of the optically active secondary allylic sulfoximines 17 and 19, chiral N-tosyl allylic secondary amines were formed in high enantiomeric purities.
• Diastereoselective Reactions and Rearrangements of Chiral Allylic Sulfoximines
  作者：Stephen G. Pyne、Z. Dong、D. M. David、G. W. O'Meara

  DOI：10.1080/10426509708545524

  日期：1997.1.1

  nucleophilic and electrophilic chemistry of chiral allylic sulfominines and their alkyl sulfoximine counterparts are described including the synthesis of highly functionalised cyclopropanes derivatives. The synthesis of primary and secondary N-tosyl allylic amines via the palladium(0) catalysed rearrangement of allylic sulfoximines to allylic sulfinamides is also described.

  摘要：描述了手性烯丙基亚磺胺及其烷基亚砜亚胺对应物的亲核和亲电化学，包括高度官能化的环丙烷衍生物的合成。还描述了通过钯 (0) 催化的烯丙基亚砜亚胺重排为烯丙基亚磺酰胺的伯和仲 N-甲苯磺酰基烯丙基胺的合成。