2,6-Dioxo-3,7-diaza-bicyclo[3.3.1]nonane-1,5-dicarboxylic acid diethyl ester | 244096-11-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,6-Dioxo-3,7-diaza-bicyclo[3.3.1]nonane-1,5-dicarboxylic acid diethyl ester
• 英文别名: diethyl 2,6-dioxo-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarboxylate
• CAS: 244096-11-5
• 化学式: C₁₃H₁₈N₂O₆
• mdl: MFCD03016985
• 分子量: 298.296
• InChiKey: HGDSPYPCTVZIRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-Dioxo-3,7-diaza-bicyclo[3.3.1]nonane-1,5-dicarboxylic acid diethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 336000.0h， 以98%的产率得到3,7-diazabicyclo[3.3.1]nonane-2,6-dione-1,5-dicarboxamide
  参考文献：
  名称：

  Competitive H-bonding in bicyclic bis-lactams: self-assembly in nanotubes or in unbalanced chiral threefold interpenetrated diamondoid network

  摘要：

  The first example of an H-bonded diamondoid network formed by a chiral molecule is reported. Diamondoid networks in the crystal structure of the described bicyclic bis-lactam are homochiral and threefold interpenetrated, two of them being of one chirality and the third of the other. Thus, unbalanced chiral packing (sp. gr. 141, z = 12) and spontaneous resolution with ee 33% is observed. A slight change in the structural formula leads to an entirely different crystal structure with nanosize channels. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00744-9
• 作为产物：
  描述：

  3,7-Bis-(4-methoxy-benzyl)-2,6-dioxo-3,7-diaza-bicyclo[3.3.1]nonane-1,5-dicarboxylic acid diethyl ester 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以52.3%的产率得到2,6-Dioxo-3,7-diaza-bicyclo[3.3.1]nonane-1,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Directed synthesis of compounds capable to spontaneous resolution

  摘要：

  A qualitative conception for constructing conglomerates has been proposed; bis-lactam 1 has been synthesised by two methods, and it exhibited a priori predicted properties like formation in the optically active form under conditions of a routine crystallization.

  DOI：

  10.1070/mc2002v012n01abeh001516

文献信息

• Directed synthesis of compounds capable to spontaneous resolution
  作者：Remir G. Kostyanovsky、Irina A. Bronzova、Konstantin A. Lyssenko

  DOI：10.1070/mc2002v012n01abeh001516

  日期：2002.1

  A qualitative conception for constructing conglomerates has been proposed; bis-lactam 1 has been synthesised by two methods, and it exhibited a priori predicted properties like formation in the optically active form under conditions of a routine crystallization.
• Competitive H-bonding in bicyclic bis-lactams: self-assembly in nanotubes or in unbalanced chiral threefold interpenetrated diamondoid network
  作者：Remir G. Kostyanovsky、Konstantin A. Lyssenko、Denis A. Lenev、Irina A. Bronzova

  DOI：10.1016/s0957-4166(02)00744-9

  日期：2002.12

  The first example of an H-bonded diamondoid network formed by a chiral molecule is reported. Diamondoid networks in the crystal structure of the described bicyclic bis-lactam are homochiral and threefold interpenetrated, two of them being of one chirality and the third of the other. Thus, unbalanced chiral packing (sp. gr. 141, z = 12) and spontaneous resolution with ee 33% is observed. A slight change in the structural formula leads to an entirely different crystal structure with nanosize channels. (C) 2002 Elsevier Science Ltd. All rights reserved.