(S)-S-phenyl-2-<(E)-2-phenylethenyl>-N-<(p-tolyl)sulfonyl>sulfoximid | 102817-12-9

• 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)-S-phenyl-2-<(E)-2-phenylethenyl>-N-<(p-tolyl)sulfonyl>sulfoximid
• 英文别名: (S)-S-phenyl-2-((E)-2-phenylethenyl)-N-[(p-tolyl)sulfonyl]sulfoximid；4-methyl-N-[oxo-phenyl-[(E)-2-phenylethenyl]-λ6-sulfanylidene]benzenesulfonamide
• CAS: 102817-12-9
• 化学式: C₂₁H₁₉NO₃S₂
• 分子量: 397.519
• InChiKey: OOEQECUIQKXHKV-ZOGILVBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  63.57
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-S-phenyl-2-<(E)-2-phenylethenyl>-N-<(p-tolyl)sulfonyl>sulfoximid 、 二苯基膦 在 potassium tert-butylate 、 三氟化硼四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 生成 、
  参考文献：
  名称：

  Synthesis of 1,5-P,N-phosphino-sulfoximines through phospha-Michael reaction of alkenyl sulfoximines and their evaluation as ligands in palladium-catalyzed allylic alkylation

  摘要：

  We describe a modular synthesis of cyclic and acyclic 1,5-P,N-phosphino-sulfoximines by using a phospha-Michael reaction of the corresponding alkenyl sulfoximines with HPPh2/KOtBu as key step, which proceeds with medium diastereoselectivity. The palladium-catalyzed allylic alkylation of racemic 1,3-diphenyl allyl acetate with malonate in the presence of a SSRCRC-configured N-benzyl-substituted cyclic phosphino-sulfoximine gave the corresponding alkene with 97% ee in 98% yield. A comparative study of N-substituted phosphino-sulfoximines showed the selectivity of the Pd(0)-catalyst to be dependent not only on the chiral backbone of the ligand but also on the N-substituent and configuration of the sulfoximine group. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.006
• 作为产物：
  描述：

  在 1,2-diazabicyclo[5.4.0]undec-7-ene 作用下， 生成 (S)-S-phenyl-2-<(E)-2-phenylethenyl>-N-<(p-tolyl)sulfonyl>sulfoximid
  参考文献：
  名称：

  Synthesis of 1,5-P,N-phosphino-sulfoximines through phospha-Michael reaction of alkenyl sulfoximines and their evaluation as ligands in palladium-catalyzed allylic alkylation

  摘要：

  We describe a modular synthesis of cyclic and acyclic 1,5-P,N-phosphino-sulfoximines by using a phospha-Michael reaction of the corresponding alkenyl sulfoximines with HPPh2/KOtBu as key step, which proceeds with medium diastereoselectivity. The palladium-catalyzed allylic alkylation of racemic 1,3-diphenyl allyl acetate with malonate in the presence of a SSRCRC-configured N-benzyl-substituted cyclic phosphino-sulfoximine gave the corresponding alkene with 97% ee in 98% yield. A comparative study of N-substituted phosphino-sulfoximines showed the selectivity of the Pd(0)-catalyst to be dependent not only on the chiral backbone of the ligand but also on the N-substituent and configuration of the sulfoximine group. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.006

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。
• Strukturaufklärung ungewöhnlicher Umlagerungsprodukte von<i>S</i>-(1-Alkenyl)sulfoximiden mit Hilfe der Stossaktivierungsmassenspektrometrie (CAD-MS)
  作者：Hans-Jürgen Veith、Hans-Joachim Gais、Irene Erdelmeier

  DOI：10.1002/hlca.19870700416

  日期：1987.7.8

  Structure Determination of Unusual Rearrangement Products of S-(1-Alkenyl)sulfoximides by Collisionally Activated Dissoication Mass Spectrometry (CAD-MS)

  碰撞活化解离质谱法（CAD-MS）确定S-（1-烯基）亚磺酰亚胺的异常重排产物的结构
• ERDELMEIER, I.;GAIS, H. -J., TETRAHEDRON LETT., 1985, 26, N 36, 4359-4362
  作者：ERDELMEIER, I.、GAIS, H. -J.

  DOI：——

  日期：——
• Synthesis of 1,5-P,N-phosphino-sulfoximines through phospha-Michael reaction of alkenyl sulfoximines and their evaluation as ligands in palladium-catalyzed allylic alkylation
  作者：Fabien Lemasson、Hans-Joachim Gais、Gerhardt Raabe

  DOI：10.1016/j.tetlet.2007.10.006

  日期：2007.12

  We describe a modular synthesis of cyclic and acyclic 1,5-P,N-phosphino-sulfoximines by using a phospha-Michael reaction of the corresponding alkenyl sulfoximines with HPPh2/KOtBu as key step, which proceeds with medium diastereoselectivity. The palladium-catalyzed allylic alkylation of racemic 1,3-diphenyl allyl acetate with malonate in the presence of a SSRCRC-configured N-benzyl-substituted cyclic phosphino-sulfoximine gave the corresponding alkene with 97% ee in 98% yield. A comparative study of N-substituted phosphino-sulfoximines showed the selectivity of the Pd(0)-catalyst to be dependent not only on the chiral backbone of the ligand but also on the N-substituent and configuration of the sulfoximine group. (c) 2007 Elsevier Ltd. All rights reserved.