(2S,2'S)-2,2'-bimorpholine | 389633-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (2S,2'S)-2,2'-bimorpholine
• 英文别名: (2S)-2-[(2S)-morpholin-2-yl]morpholine
• CAS: 389633-52-7
• 化学式: C₈H₁₆N₂O₂
• 分子量: 172.227
• InChiKey: UQIXYRYDDGPJRI-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  42.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,2'S)-2,2'-bimorpholine 在 盐酸 、 tris-(dibenzylideneacetone)dipalladium(0) 、 水 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 7,7'-((2S,2'S)-[2,2'-bimorpholine]-4,4'-diyl)bis(1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid)
  参考文献：
  名称：

  Amination of quinolones with morpholine derivatives

  摘要：

  The aromatic nucleophilic substitution reaction of 7-chloroquinolone carboxylic acid and its ethyl ester with cyclic amines under microwave irradiation conditions was investigated H-1 NMR spectroscopy was used to monitor the progress of the substitution reaction. The reaction proceeded in high yield with simple cyclic amines and was less efficient for sterically more demanding bimorpholine derivatives. A Pd-catalyzed amination of quinolone carboxylic acid ethyl ester with bimorpholine derivatives provided new C-7 bimorpholino-substituted quinolone derivatives. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.082
• 作为产物：
  描述：

  (4R,5R)-N,N'-bis(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxamide 在 palladium on activated charcoal 盐酸 、 lithium aluminium tetrahydride 、 ammonium formate 、 sodium hydride 、 potassium carbonate 、 1-对甲基苯磺酰咪唑 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 59.0h， 生成 (2S,2'S)-2,2'-bimorpholine
  参考文献：
  名称：

  Synthesis of (2S,2′S)-bimorpholine N,N′-quaternary salts as chiral phase transfer catalysts

  摘要：

  (2S,2'S)-二吗啉从(R,R)- tartaric酸酯乙缩醛出发，经过六步反应，总产率为50%。关键步骤包括：氰化物催化的酰胺化和邻甲苯基乙酰亚胺一步环化。N,N-二苯基二吗啉的衍生物提供了四元二吗啉盐，用作手性相转移烷基化催化剂。© 2007 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.tetasy.2007.01.004

文献信息

• Asymmetric synthesis of novel C2-symmetric bimorpholines
  作者：Tõnis Kanger、Kadri Kriis、Tõnis Pehk、Aleksander-Mati Müürisepp、Margus Lopp

  DOI：10.1016/s0957-4166(02)00188-x

  日期：2002.5

  Novel heterocycles-(2S,2'S)-bimorpholine 1 and (3S,3'S)-bimorpholine 2-were synthesised in >98% e.e. starting from tartaric acid ester. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Amination of quinolones with morpholine derivatives
  作者：Kristin Lippur、Tõnis Tiirik、Marina Kudrjashova、Ivar Järving、Margus Lopp、Tõnis Kanger

  DOI：10.1016/j.tet.2012.09.082

  日期：2012.11

  The aromatic nucleophilic substitution reaction of 7-chloroquinolone carboxylic acid and its ethyl ester with cyclic amines under microwave irradiation conditions was investigated H-1 NMR spectroscopy was used to monitor the progress of the substitution reaction. The reaction proceeded in high yield with simple cyclic amines and was less efficient for sterically more demanding bimorpholine derivatives. A Pd-catalyzed amination of quinolone carboxylic acid ethyl ester with bimorpholine derivatives provided new C-7 bimorpholino-substituted quinolone derivatives. (c) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of (2S,2′S)-bimorpholine N,N′-quaternary salts as chiral phase transfer catalysts
  作者：Kristin Lippur、Tõnis Kanger、Kadri Kriis、Tiiu Kailas、Aleksander-Mati Müürisepp、Tõnis Pehk、Margus Lopp

  DOI：10.1016/j.tetasy.2007.01.004

  日期：2007.1

  (2S,2'S)-Bimorpholine was synthesized starting from (R,R)-tartaric acid ester acetal in six steps in 50% of the total yield. Key steps include: cyanide catalyzed amidation and one-step cyclization with p-toluenesulfonyl imidazole. Derivatization of N,N-dibenzyl bimorpholine afforded quaternary bimorpholinium salts, which were used as chiral phase transfer alkylation catalysts. (c) 2007 Elsevier Ltd. All rights reserved.

  (2S,2'S)-二吗啉从(R,R)- tartaric酸酯乙缩醛出发，经过六步反应，总产率为50%。关键步骤包括：氰化物催化的酰胺化和邻甲苯基乙酰亚胺一步环化。N,N-二苯基二吗啉的衍生物提供了四元二吗啉盐，用作手性相转移烷基化催化剂。© 2007 Elsevier Ltd. 保留所有权利。