(S)-2-methyl-N-(pyridin-3-ylmethylene)propane-2-sulfinamide | 1272676-08-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-2-methyl-N-(pyridin-3-ylmethylene)propane-2-sulfinamide
• 英文别名: (S)-2-methyl-N-(pyridin-3-ylmethylidene)propane-2-sulfinamide
• CAS: 1272676-08-0
• 化学式: C₁₀H₁₄N₂OS
• 分子量: 210.3
• InChiKey: BMQNAHRVOYMEED-AWEZNQCLSA-N

物化性质

• 沸点：
  359.6±34.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-methyl-N-(pyridin-3-ylmethylene)propane-2-sulfinamide 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 0.5h， 以80%的产率得到(S)-2-methyl-N-(pyridin-3-ylmethyl)propane-2-sulfinamide
  参考文献：
  名称：

  2-Pyridylsulfinamides as effective catalysts in the asymmetric alkylation of aldehydes with diethylzinc

  摘要：

  Chiral 2-pyridylsulfinamides were shown to be effective catalysts in the alkylation of aryl and alkyl aldehydes with diethylzinc providing the corresponding alcohols in excellent enantioselectivity. Sulfinamide catalysts possessing solitary chirality at the sulfur center produced the product phenethyl alcohol in good enantioselectivity. Diastereomeric sulfinamides possessing chirality at the carbon-bearing nitrogen and at the sulfur of the sulfinamide increased the enantioselectivity of the product alcohols up to >99%. However, there is no effect of the match-mismatch pair of sulfinamide diastereomers on the outcome of the chiral induction of the product phenethyl alcohols. It was conclusively proved that chirality at the sulfur center is mandatory for obtaining good enantioselectivity in the reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.061
• 作为产物：
  描述：

  3-吡啶甲醛 、 S-叔丁基亚磺酰胺 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以94%的产率得到(S)-2-methyl-N-(pyridin-3-ylmethylene)propane-2-sulfinamide
  参考文献：
  名称：

  1,8-二氮杂双环[5.4.0]undec-7-ene介导的N-亚磺酰亚胺形成

  摘要：

  开发了一种使用 1,8-二氮杂双环 [5.4.0] undec-7-ene 制备各种芳基、杂芳基和烷基 N-亚磺酰基亚胺的简便有效的方法。除叔丁烷亚磺酰胺外，缩合对甲苯亚磺酰胺也有效。该反应在室温下进行，并在不存在酸、金属和添加剂的情况下以极好的收率产生相应的 N-亚磺酰基亚胺。该方法也可用于以克规模制备 N-亚磺酰基亚胺。使用芳基和杂芳基醇与叔丁烷亚磺酰胺和对甲苯亚磺酰胺在室温下进行一锅合成，得到相应的 N-亚磺酰亚胺，收率良好。

  DOI：

  10.1177/1747519819884146

文献信息

• Asymmetric synthesis of 2-chloroaziridines via a diastereoselective nucleophilic dichloromethylation and N-alkylation in one pot
  作者：Yuxuan Zhang、Hongchang Tian、Zhengshan Luo、Xiongtong Liu、Yinjiao Zhao、Wen Chen、Hongbin Zhang

  DOI：10.1016/j.tetlet.2018.07.056

  日期：2018.9

  A diastereoselective nucleophilic dichloromethylation between the N-tert-butanesulfinyl imines and dichloromethyllithium was developed. A series of 2-chloroaziridines with excellent yields and dr values were obtained via this nucleophilic addition and N-alkylation in one pot. On the basis of X-ray crystallography experiment, the predicting model for this diastereoselective transformation was provided

  的之间的非对映选择性亲核dichloromethylation ñ -叔-butanesulfinyl亚胺和dichloromethyllithium被开发。通过这种亲核加成和在一个罐中进行N-烷基化，获得了一系列具有优异产率和dr值的2-氯氮丙啶。在X射线晶体学实验的基础上，提供了该非对映选择性转变的预测模型。
• Cyclopent-2-enylaluminium as allylzinc precursor for the diastereoselective allylmetallation of non-racemic imines: applications to the synthesis of enantiomerically enriched heterocycles
  作者：Michaël Coffinet、Samantha Lamy、Florian Jaroschik、Jean-Luc Vasse

  DOI：10.1039/c5ob02184g

  日期：——

  A sequential titanium-catalyzed/hydroalumination/transmetallation/allylation of non-racemic imines which provides tunable homoallylamines for heterocyclic synthesis is presented.

  一种顺序进行的钛催化/氢化铝/金属转移/烯丙基化反应，用于合成杂环化合物中可调节的同烯丙基胺。
• Diastereoselective synthesis of N-sulfinyl α-aminophosphine sulfides and phosphines
  作者：Wei Zhang、Scott R. Gilbertson

  DOI：10.1016/j.tetlet.2017.03.067

  日期：2017.6

  The diastereoselective synthesis of N-sulfinyl α-aminophosphine sulfides and phosphines is reported. These molecules are synthesized by formation of sulfinyl imine followed by diastereoselective addition of a diphenylphosphine sulfide. The product N-sulfinyl α-aminophosphine sulfides can be converted to phosphines through removal of the sulfur by reaction with Raney nickel. Hydrolysis of the sulfinyl

  报道了N-亚磺酰基α-氨基膦硫化物和膦的非对映选择性合成。这些分子是通过形成亚磺酰基亚胺，然后非对映选择性地加入二苯基膦硫化物来合成的。通过与阮内镍反应除去硫，可以将产物N-亚磺酰基α-氨基膦硫化物转化为膦。亚磺酰基的水解提供了胺，该胺然后可以连接至其他配体或结构支架。
• Indium-Promoted Diastereoselective Addition of Fluorinated Haloallylic Derivatives to Imines
  作者：Gérald Lemonnier、Nathalie Van Hijfte、Thomas Poisson、Samuel Couve-Bonnaire、Xavier Pannecoucke

  DOI：10.1021/jo402810s

  日期：2014.4.4

  We report herein the first general access to fluorinated homoallylic amines by means of an addition of fluorinated organoindium reagent. The corresponding amines were obtained in good to excellent yield with excellent diastereoisomeric ratio. A plausible mechanism is proposed to explain the stereochemical outcome of the reaction based on the X-ray structure of the products.

  我们在此报告了通过添加氟化有机铟试剂而首次获得氟化均烯丙基胺。以良好至优异的产率和优异的非对映异构体比率获得相应的胺。根据产物的X射线结构，提出了一种合理的机理来解释反应的立体化学结果。
• Highly diastereoselective addition of chiral H-phosphonate to tert-butylsulfinyl aldimines: a convenient approach to (R)-α-aminophosphonic acids
  作者：Tomasz K. Olszewski、Mateusz Majewski

  DOI：10.1016/j.tetasy.2015.06.008

  日期：2015.8

  A highly diastereoselective nucleophilic addition of chiral H-phosphonate, derived from a readily available TADDOL auxiliary, to (S)-N-tert-butylsulfinyl aldimines is reported. The reaction proceeds at room temperature in the presence of potassium carbonate and yields the corresponding aliphatic, aromatic and heteroaromatic alpha-aminophosphonates with dr >95:5. Subsequent simultaneous removal of both chiral auxiliaries leads to the desired alpha-aminophosphonic acids in very good yields with an (R)-configuration at the stereogenic alpha carbon. (C) 2015 Elsevier Ltd. All rights reserved.