(1S,5S,1'S)-6,8-bis(1'-phenylethyl)-7,9-dioxo-3-methylene-6,8-diazabicyclo[3.2.2]nonane | 530125-07-6

• 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: (1S,5S,1'S)-6,8-bis(1'-phenylethyl)-7,9-dioxo-3-methylene-6,8-diazabicyclo[3.2.2]nonane
• 英文别名: (1S,5S)-3-methylidene-6,8-bis[(1S)-1-phenylethyl]-6,8-diazabicyclo[3.2.2]nonane-7,9-dione
• CAS: 530125-07-6
• 化学式: C₂₄H₂₆N₂O₂
• 分子量: 374.483
• InChiKey: JBBJLQJKUCPUQH-GPHNJDIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,5S,1'S)-6,8-bis(1'-phenylethyl)-7,9-dioxo-3-methylene-6,8-diazabicyclo[3.2.2]nonane 在 盐酸 、 氨 、 甲基锂 、 lithium 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 12.08h， 生成 (2S,6S)-2-allyl-2,6-diamino-4-methylene-1,7-heptanedioic acid dihydrochloride
  参考文献：
  名称：

  Stereocontrolled synthesis of enantiomerically pure unsaturated analogues of 2,6-DAP. Part 5

  摘要：

  An efficient new stereocontrolled synthesis of (2R,6R)-(+)- and (2S,6S)-(-)-2,6-diamino-4-methylene-1,7-heptanedioic acid 8a and 9a, respectively, has been accomplished starting from the glycine-derived chiral synthon 1. The enantiomerically pure alpha-alkyl derivatives 8b-d and 9b-d have also been synthesized. The absolute configuration of the new stereocenters was assigned on the basis of H-1 NMR spectra. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00834-0
• 作为产物：
  描述：

  3-氯-2-氯甲基丙烯 、 1,4-bis((S)-1-phenylethyl)piperazine-2,5-dione 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到(1S,5S,1'S)-6,8-bis(1'-phenylethyl)-7,9-dioxo-3-methylene-6,8-diazabicyclo[3.2.2]nonane
  参考文献：
  名称：

  Stereocontrolled synthesis of enantiomerically pure unsaturated analogues of 2,6-DAP. Part 5

  摘要：

  An efficient new stereocontrolled synthesis of (2R,6R)-(+)- and (2S,6S)-(-)-2,6-diamino-4-methylene-1,7-heptanedioic acid 8a and 9a, respectively, has been accomplished starting from the glycine-derived chiral synthon 1. The enantiomerically pure alpha-alkyl derivatives 8b-d and 9b-d have also been synthesized. The absolute configuration of the new stereocenters was assigned on the basis of H-1 NMR spectra. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00834-0

文献信息

• Stereocontrolled synthesis of enantiomerically pure unsaturated analogues of 2,6-DAP. Part 5
  作者：Fabio Piccinelli、Gianni Porzi、Monica Sandri、Sergio Sandri

  DOI：10.1016/s0957-4166(02)00834-0

  日期：2003.2

  An efficient new stereocontrolled synthesis of (2R,6R)-(+)- and (2S,6S)-(-)-2,6-diamino-4-methylene-1,7-heptanedioic acid 8a and 9a, respectively, has been accomplished starting from the glycine-derived chiral synthon 1. The enantiomerically pure alpha-alkyl derivatives 8b-d and 9b-d have also been synthesized. The absolute configuration of the new stereocenters was assigned on the basis of H-1 NMR spectra. (C) 2003 Elsevier Science Ltd. All rights reserved.