(R,E)-2-methyl-N-(quinolin-8-ylmethylene)propane-2-sulfinamide | 455891-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (R,E)-2-methyl-N-(quinolin-8-ylmethylene)propane-2-sulfinamide
• 英文别名: (NE,R)-2-methyl-N-(quinolin-8-ylmethylidene)propane-2-sulfinamide
• CAS: 455891-04-0
• 化学式: C₁₄H₁₆N₂OS
• 分子量: 260.36
• InChiKey: RLINXQRVXQWYJH-GANRHZMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (R,E)-2-methyl-N-(quinolin-8-ylmethylene)propane-2-sulfinamide 、 (S)-4-benzyl-5,5-dimethyl-3-propionyloxazolidin-2-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以47%的产率得到(R)-N-((1R,2R)-3-((S)-4-benzyl-5,5-dimethyl-2-oxooxazolidin-3-yl)-2-methyl-3-oxo-1-(quinolin-8-yl)propyl)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Diastereoselective Synthesis of β-Heteroaryl syn-α-Methyl-β-Amino Acid Derivatives via a Double Chiral Auxiliary Approach

  摘要：

  The addition of the SuperQuat enolate to five- and six-membered heterocyclic tert-butyl sulfinimines led to a high syn-selectivity of up to 99:1 in good to excellent yields. The reaction Is tentatively proposed to proceed through an open-chain transition state with the presence of an alpha-heteroatom on the sulfinimine leading to high diastereoselectivities. The adducts were derivatized to beta-amino esters and amides in a facile manner.

  DOI：

  10.1021/ol3033785
• 作为产物：
  描述：

  喹啉-8-甲醛 、 (R)-(+)-叔丁基亚磺酰胺 在 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到(R,E)-2-methyl-N-(quinolin-8-ylmethylene)propane-2-sulfinamide
  参考文献：
  名称：

  Diastereoselective Synthesis of β-Heteroaryl syn-α-Methyl-β-Amino Acid Derivatives via a Double Chiral Auxiliary Approach

  摘要：

  The addition of the SuperQuat enolate to five- and six-membered heterocyclic tert-butyl sulfinimines led to a high syn-selectivity of up to 99:1 in good to excellent yields. The reaction Is tentatively proposed to proceed through an open-chain transition state with the presence of an alpha-heteroatom on the sulfinimine leading to high diastereoselectivities. The adducts were derivatized to beta-amino esters and amides in a facile manner.

  DOI：

  10.1021/ol3033785

文献信息

• Asymmetric process for the preparation of diarylethylpiperazines derivatives and novel asymmetric diarylmethylamines as intermediates
  申请人：——

  公开号：US20040077861A1

  公开（公告）日：2004-04-22

  An asymmetric synthesis of diarylmethylpiperazines is described. The synthetic route enables preparation of a variety of enatiomerically pure amines with different N-alkyl groups. The invention includes an asymmetric addition of organometallic compounds to chiral sulfinimine to give adducts in predominantly one diastereomer can subsequently be transferred into pure enantiomers of by cleavage of the chiral auxilliary which is followed by synthesis of the piperazine ring by alkylation procedures.

  本文介绍了一种二苯甲基哌嗪的不对称合成方法。该合成路线可以制备具有不同N-烷基的对映纯氨基化合物。该发明包括有机金属化合物不对称加成到手性亚磺酰胺中，形成主要一种对映异构体的加合物，随后通过手性辅助基的裂解转化为纯对映体，再通过烷基化方法合成哌嗪环。
• NEW ASYMMETRIC PROCESS FOR THE PREPARATION OF DIARYLMETHYLPIPERAZINES DERIVATIVES AND NOVEL ASYMMETRIC DIARYLMETYLAMINES AS INTERMEDIATES
  申请人：AstraZeneca AB

  公开号：EP1368325B1

  公开（公告）日：2008-08-27
• US7045625B2
  申请人：——

  公开号：US7045625B2

  公开（公告）日：2006-05-16
• US7423154B2
  申请人：——

  公开号：US7423154B2

  公开（公告）日：2008-09-09
• [EN] NEW ASYMMETRIC PROCESS FOR THE PREPARATION OF DIARYLMETHYLPIPERAZINES DERIVATIVES AND NOVEL ASYMMETRIC DIARYLMETYLAMINES AS INTERMEDIATES<br/>[FR] NOUVEAU PROCEDE ASYMETRIQUE DE PREPARATION DE DERIVES DE DIARYLMETHYLPIPERAZINES ET NOUVELLES DIARYLMETHYLAMINES ASYMETRIQUES EN TANT QU'INTERMEDIAIRES
  申请人：ASTRAZENECA AB

  公开号：WO2002070492A1

  公开（公告）日：2002-09-12

  An asymmetric synthesis of diarylmethylpiperazines is described. The synthetic route enables preparation of a variety of enatiomerically pure amines with different N-alkyl groups. The invention includes an asymmetric addition of organometallic compounds to chiral sulfinimine to give adducts in predominantly one diastereomer can subsequently be transferred into pure enantiomers of by cleavage of the chiral auxilliary which is followed by synthesis of the piperazine ring by alkylation procedures.