(2S,3S)-N,N'-dibenzyl-2,3-diamino-1,4-butanediol | 335162-29-3

• 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: (2S,3S)-N,N'-dibenzyl-2,3-diamino-1,4-butanediol
• 英文别名: (2S,3S)-2,3-dibenzylaminobutane-1,4-diol；(2S,3S)-2,3-bis(benzylamino)butane-1,4-diol
• CAS: 335162-29-3
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: TXMQWPOKFMKNFY-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-N,N'-dibenzyl-2,3-diamino-1,4-butanediol 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 1.5h， 生成 (1S,6S)-2,7-di(N-benzyl)aza-4,9-dioxabicyclo[4.4.0]decane
  参考文献：
  名称：

  Synthesis of New Chiral Mixedcis-Tetraheterodecalines by Highly Selective Cyclization ofN,N′-Bisalkyl 2,3-Diaminobutanediols

  摘要：

  从 l-酒石酸中高效地制备出了二氨基丁二醇手性仲烷基二胺。通过对它们进行选择性环化，得到了具有 (1S,6S)-2,7- 二氮杂-4,9-二氧杂[4.4.0]癸烷核心系统的顺式四庚烷。

  DOI：

  10.1055/s-2006-926389
• 作为产物：
  描述：

  (5S,5'S)-N,N-dibenzyl-5,5'-bis(oxazolidin-2-one) 在 lithium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 以81%的产率得到(2S,3S)-N,N'-dibenzyl-2,3-diamino-1,4-butanediol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)00446-8

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 New Chiral Mixed<i>cis</i>-Tetraheterodecalines by Highly Selective Cyclization of<i>N</i>,<i>N</i>′-Bisalkyl 2,3-Diaminobutanediols
  作者：Jean-Louis Gras、Eric Taulier

  DOI：10.1055/s-2006-926389

  日期：——

  Chiral secondary vic-diamines of diaminobutanediols have been efficiently prepared from l-tartaric acid. Their selective cyclization led to cis-tetraheterodecalines having a (1S,6S)-2,7-di­aza-4,9-dioxa[4.4.0]decane core system.

  从 l-酒石酸中高效地制备出了二氨基丁二醇手性仲烷基二胺。通过对它们进行选择性环化，得到了具有 (1S,6S)-2,7- 二氮杂-4,9-二氧杂[4.4.0]癸烷核心系统的顺式四庚烷。