(S,E)-N-(4-bromobenzylidene)-4-methylbenzenesulfinamide | 479692-22-3

• 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,E)-N-(4-bromobenzylidene)-4-methylbenzenesulfinamide
• 英文别名: (S)-(+)-N-(4-bromobenzylidene)-p-toluenesulfinamide；(S)-(+)-N-(p-bromobenzylidene)-p-toluenesulfinamide；(NE,S)-N-[(4-bromophenyl)methylidene]-4-methylbenzenesulfinamide
• CAS: 479692-22-3
• 化学式: C₁₄H₁₂BrNOS
• 分子量: 322.225
• InChiKey: BRNBYBUSFPBCDT-BXBHGGAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,E)-N-(4-bromobenzylidene)-4-methylbenzenesulfinamide 在 盐酸 、 溶剂黄146 、 naphthalen-1-yl-lithium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.5h， 生成 (S)-N-phthaloyl-1-amino-1-(p-bromophenyl)methylphosphonic acid
  参考文献：
  名称：

  A new efficient procedure for asymmetric synthesis of α-aminophosphonic acids via addition of lithiated bis(diethylamino)phosphine borane complex to enantiopure sulfinimines

  摘要：

  The addition of lithiated bis(diethylamino)phosphine borane complex to enantiopure p-toluenesulfinimines is highly diastereoselective, affording the corresponding addition products with high efficiency (yields from 72 to 100%). The addition products were readily converted into alpha-amino-alpha-arylmethylphosphonic acids with high enantiomeric purities (from 72 to >98%). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00684-5
• 作为产物：
  描述：

  对溴苯甲醛 、 (S)-(+)-对甲基苯亚磺酰胺 在 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (S,E)-N-(4-bromobenzylidene)-4-methylbenzenesulfinamide
  参考文献：
  名称：

  使用 Cs2CO3 作为活化和脱水试剂，通过亚磺酰胺与醛的直接缩合合成亚磺亚胺

  摘要：

  在作为胺活化和脱水试剂的碳酸铯存在下，在 CH 2 Cl 2 中，由手性亚磺酰胺和醛制备手性亚磺亚胺。

  DOI：

  10.1055/s-2004-815409

文献信息

• Triisopropyl borate mediated N -sulfinyl imine formation
  作者：Michael D. Visco、Jonathan T. Reeves、Maurice A. Marsini、Ivan Volchkov、Carl A. Busacca、Anita E. Mattson、Chris H. Senanayake

  DOI：10.1016/j.tetlet.2016.03.063

  日期：2016.4

  Triisopropyl borate effects the condensation of aldehydes with sulfinamides to give N-sulfinyl imines. The reaction is amenable to 1°, 2°, and 3° alkyl aldehydes, as well as aryl, heteroaryl, and α,β-unsaturated aldehydes. In addition to tert-butanesulfinamide, the condensation is also effective with 4-toluenesulfinamide and 2,4,6-triisopropylphenylsulfinamide. This protocol proceeds under homogeneous

  硼酸三异丙酯使醛与亚磺酰胺缩合，生成N-亚磺酰基亚胺。该反应适合于1°，2°和3°烷基醛，以及芳基，杂芳基和α，β-不饱和醛。除叔丁烷亚磺酰胺外，缩合反应还与4-甲苯亚磺酰胺和2,4,6-三异丙基苯基亚磺酰胺有效。该方案在均相反应条件下进行，不需要不溶试剂或副产物的反应后过滤。
• Diastereoselective Trifluoromethylation of Chiral<i>N</i>-(Tolylsulfinyl)imines in the Presence of Lewis Bases
  作者：Yoshikazu Kawano、Teruaki Mukaiyama

  DOI：10.1246/cl.2005.894

  日期：2005.7

  A diastereoselctive trifluoromethylation of chiral N-(tolylsulfinyl)imines with (trifluoromethyl)trimethylsilane in the presence of Lewis bases such as tetrabutylammonium acetate or phenoxide proceeded smoothly to afford the corresponding trifluoromethylated adducts in good yields.

  一种在路易斯碱（如四丁基铵乙酸盐或酚氧基）存在下，利用(trifluoromethyl)trimethylsilane对手性N-(托烯基亚磺酰)亚胺进行的非对映体选择性三氟甲基化反应顺利进行，产物获得了良好的产率。
• Lewis Base-catalyzed Diastereoselective Mannich-type Reaction between Ketene Silyl Acetals and Chiral Sulfinimines
  作者：Eiki Takahashi、Hidehiko Fujisawa、Toshiharu Yanai、Teruaki Mukaiyama

  DOI：10.1246/cl.2005.468

  日期：2005.4

  Lewis base-catalyzed diastreoselective Mannich-type reaction between ketene silyl acetals and chiral sulfinimines proceeded smoothly to afford the corresponding β-amino carbonyl compounds in good to high yields with high selectivities.

  Lewis碱催化的二面体选择性Mannich反应在酮烯硅醇酯和手性亚磺酰胺之间顺利进行，得到了相应的β-氨基酮羧化合物，产率良好到很高，选择性高。
• A General Method for Imine Formation Using B(OCH₂CF₃)₃
  作者：Jonathan T. Reeves、Michael D. Visco、Maurice A. Marsini、Nelu Grinberg、Carl A. Busacca、Anita E. Mattson、Chris H. Senanayake

  DOI：10.1021/acs.orglett.5b00949

  日期：2015.5.15

  Tris(2,2,2-trifluoroethyl)borate [B(OCH2CF3)(3)] was found to be a mild and general reagent for the formation of a variety of imines by condensation of amides or amines with carbonyl compounds. N-Sulfinyl, N-toluenesulfonyl, N-(dimethylamino)sulfamoyl, N-diphenylphosphinoyl, N-(alpha-methylbenzyl), and N-(4-methoxyphenyl) aldimines are all accessible using this reagent at room temperature. The reactions are operationally simple, and the products are obtained without special workup or isolation procedures.
• A Highly Diastereoselective MgI₂-Mediated Ring Expansion of Methylenecyclopropanes
  作者：Mark E. Scott、Wooseok Han、Mark Lautens

  DOI：10.1021/ol048769u

  日期：2004.9.1

  A highly diastereoselective MgI2-mediated ring expansion of methylenecyclopropane amides to functionalized pyrrolidines has been developed using chiral aromatic sulfinimines. The 2,3,4-trisubstituted pyrrolidines were isolated in generally good to excellent yields and in excellent diastereoselectivities for aromatic and heterocyclic sulfinimines.