(5S,5'S)-N,N-dibenzyl-5,5'-bis(oxazolidin-2-one) | 285979-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (5S,5'S)-N,N-dibenzyl-5,5'-bis(oxazolidin-2-one)
• 英文别名: (4S)-3-benzyl-4-[(4S)-3-benzyl-2-oxo-1,3-oxazolidin-4-yl]-1,3-oxazolidin-2-one
• CAS: 285979-96-6
• 化学式: C₂₀H₂₀N₂O₄
• 分子量: 352.39
• InChiKey: FNZOLJATRTWHSY-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,5'S)-N,N-dibenzyl-5,5'-bis(oxazolidin-2-one) 在 氨 、 sodium 作用下， 以72%的产率得到(4S)-4-[(4S)-2-oxo-1,3-oxazolidin-4-yl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of the first water-soluble C 2 -symmetric bis(oxazolidinone) as a potential bifunctional chiral auxiliary

  摘要：

  The first water-soluble C-2-symmetric bis(oxazolidinone) 1, a potential bifunctional chiral auxiliary, has been synthesized via regioselective intramolecular cyclization of a biscarbamate. The sodium enolate derived from N,N'-di(phenylacetyl)bis(oxazolidinone) 7 reacts with methyl iodide with high facial selectivity (95:5). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00086-0
• 作为产物：
  描述：

  (2S,3S)-2,3-di(methanesulfonyloxy)-1,4-di(N,N'-dibenzylaminocarbonyloxy)butane 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(5S,5'S)-N,N-dibenzyl-5,5'-bis(oxazolidin-2-one)
  参考文献：
  名称：

  Synthesis of the first water-soluble C 2 -symmetric bis(oxazolidinone) as a potential bifunctional chiral auxiliary

  摘要：

  The first water-soluble C-2-symmetric bis(oxazolidinone) 1, a potential bifunctional chiral auxiliary, has been synthesized via regioselective intramolecular cyclization of a biscarbamate. The sodium enolate derived from N,N'-di(phenylacetyl)bis(oxazolidinone) 7 reacts with methyl iodide with high facial selectivity (95:5). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00086-0

文献信息

• One-pot synthesis of C2-symmetric N,N′-diaryl bis(oxazolidin-2-ones) as precursors for N,N′-diaryl 2,3-diamino-1,4-butanediols
  作者：Sang-gi Lee、Chung Woo Lim、Jae Kyun Lee、Ok-Sang Jung、Young-A Lee

  DOI：10.1016/s0957-4166(00)00446-8

  日期：2000.12

  A new and general one-pot synthetic method for C-2-symmetric N,N'-aryl-disubstituted bis(oxazolidin-2-ones) has been developed. Highly regioselective intramolecular cyclization reactions of 2,3-di(methanesulfonyloxy)-1,4-dihydroxybutane with arylisocyanates in the presence of sodium hydride afforded the corresponding C-2-symmetric N,N'-aryl-disubstituted bis(oxazolidin-2-ones) in 82-92% yields. Hydrolytic ring opening of the bis(oxazolidin-2-ones) provided a convenient synthetic route for optically pure C-2-symmetric N,N'-aryl-disubstituted 2,3-diamino-1,4-butanediols (58-86% yields). (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of the first water-soluble C 2 -symmetric bis(oxazolidinone) as a potential bifunctional chiral auxiliary
  作者：Sang-gi Lee、Chung Woo Lim、Dong Chan Kim、Jae Kyun Lee

  DOI：10.1016/s0957-4166(00)00086-0

  日期：2000.4

  The first water-soluble C-2-symmetric bis(oxazolidinone) 1, a potential bifunctional chiral auxiliary, has been synthesized via regioselective intramolecular cyclization of a biscarbamate. The sodium enolate derived from N,N'-di(phenylacetyl)bis(oxazolidinone) 7 reacts with methyl iodide with high facial selectivity (95:5). (C) 2000 Elsevier Science Ltd. All rights reserved.