(1S,9S)-9-[(naphthalen-2-ylmethylene)-amino]-6,10-dioxo-octahydro-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid tert-butyl ester | 625415-54-5

• 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: (1S,9S)-9-[(naphthalen-2-ylmethylene)-amino]-6,10-dioxo-octahydro-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S,7S)-7-(naphthalen-2-ylmethylideneamino)-6,10-dioxo-2,3,4,7,8,9-hexahydro-1H-pyridazino[1,2-a]diazepine-4-carboxylate
• CAS: 625415-54-5
• 化学式: C₂₅H₂₉N₃O₄
• 分子量: 435.523
• InChiKey: SAATYSUTTFSGRP-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5R)-(L-menthyloxy)-2(5H)-furanone 、 (1S,9S)-9-[(naphthalen-2-ylmethylene)-amino]-6,10-dioxo-octahydro-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid tert-butyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以81%的产率得到tert-butyl (1'R,3'aR,4S,4'S,6'aS,7R)-1'-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-4'-naphthalen-2-yl-3',6,10-trioxospiro[1,2,3,4,8,9-hexahydropyridazino[1,2-a]diazepine-7,6'-3a,4,5,6a-tetrahydro-1H-furo[3,4-c]pyrrole]-4-carboxylate
  参考文献：
  名称：

  X=Y=ZH Systems as potential 1,3-dipoles. Part 58: Cycloaddition route to chiral conformationally constrained (R)-pro-(S)-pro peptidomimetics

  摘要：

  Imines of (1S,9S)-t-butyl-9-amino-octahydro-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate undergo thermal (toluene, 110degreesC) or LiBr-DBU catalysed (MeCN, room temperature) regio- and stereo-specific cycloaddition to a range of chiral dipolarophiles giving enantiopure spiro-cycloadducts in excellent yield. The reactions proceed via intermediate NH azomethine ylides and litho azomethine ylides, respectively and results in the multiplication of chiral centres from 2 (one of which is lost in the process) to 5. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.032
• 作为产物：
  描述：

  (1S,9S)-9-(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)八氢-6,10-二氧代-6H-哒嗪并[1,2-a][1,2]二氮杂卓-1-羧酸叔丁酯 在 4 A molecular sieve 、 一水合肼 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,9S)-9-[(naphthalen-2-ylmethylene)-amino]-6,10-dioxo-octahydro-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  X=Y=ZH Systems as potential 1,3-dipoles. Part 58: Cycloaddition route to chiral conformationally constrained (R)-pro-(S)-pro peptidomimetics

  摘要：

  Imines of (1S,9S)-t-butyl-9-amino-octahydro-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate undergo thermal (toluene, 110degreesC) or LiBr-DBU catalysed (MeCN, room temperature) regio- and stereo-specific cycloaddition to a range of chiral dipolarophiles giving enantiopure spiro-cycloadducts in excellent yield. The reactions proceed via intermediate NH azomethine ylides and litho azomethine ylides, respectively and results in the multiplication of chiral centres from 2 (one of which is lost in the process) to 5. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.032