N-benzyloxycarbonyl-3α-hydroxy-6-aza-7-oxabicyclo[3.2.2]non-8-ene

• 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: N-benzyloxycarbonyl-3α-hydroxy-6-aza-7-oxabicyclo[3.2.2]non-8-ene
• 英文别名: benzyl (1S,3S,5R)-3-hydroxy-6-oxa-7-azabicyclo[3.2.2]non-8-ene-7-carboxylate
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: RCPMMSMCAFRYKZ-RDBSUJKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-3α-hydroxy-6-aza-7-oxabicyclo[3.2.2]non-8-ene 在 咪唑 、 lithium aluminium tetrahydride 、 正丁基锂 、 sodium amalgam 、 tetramethylammonium metaperiodate 、 四丁基氟化铵 、 sodium hydride 、 间氯过氧苯甲酸 、 sodium phosphate 、 lithium chloride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醚 、 二甲基亚砜 为溶剂， 反应 26.17h， 生成 Scopine
  参考文献：
  名称：

  Total synthesis of scopine, pseudoscopine, and nor- derivatives

  摘要：

  Scopine and pseudoscopine have been synthesised from cyclohepta-3.5-dienol: the initial 1,4-fuctionalisation of the diene is based on a nitroso-cycloaddition. The use of the N-benzyloxycarbonyl group throughout the scheme allows ultimate reductive deprotection to yield N-methyl or novel NH (nor-) derivatives without damage to the exo-epoxide of the title compounds. Preliminary investigation of nitroso- cycloaddition to 5,6-epoxycyclohepta-1.3-diene is described. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0040-4020(96)00693-x
• 作为产物：
  描述：

  Tropilidenoxid 在 lithium aluminium tetrahydride 、 tetramethylammonium metaperiodate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-benzyloxycarbonyl-3α-hydroxy-6-aza-7-oxabicyclo[3.2.2]non-8-ene
  参考文献：
  名称：

  Total synthesis of scopine, pseudoscopine, and nor- derivatives

  摘要：

  Scopine and pseudoscopine have been synthesised from cyclohepta-3.5-dienol: the initial 1,4-fuctionalisation of the diene is based on a nitroso-cycloaddition. The use of the N-benzyloxycarbonyl group throughout the scheme allows ultimate reductive deprotection to yield N-methyl or novel NH (nor-) derivatives without damage to the exo-epoxide of the title compounds. Preliminary investigation of nitroso- cycloaddition to 5,6-epoxycyclohepta-1.3-diene is described. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0040-4020(96)00693-x

文献信息

• Total synthesis of 1-hydroxytropacocaine and analogues
  作者：John R. Malpass、Anna L. Wallis

  DOI：10.1016/s0040-4020(98)00095-7

  日期：1998.4

  The first synthesis of the title alkaloid (1) (+/- 3-beta-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octan-1-ol) is described from cyclohepta-3,5-dienol. The approach is extended to novel variants including the unknown nor-analogue (3) and a derivative of the 6,7-dehydro-system. Detailed NMR data are presented. VT NMR studies show that (1) is effectively bicyclic, although there is evidence confirming the occurrence of tautomerism involving the monocyclic amino-ketone; in contrast, N-benzyloxycarbonyl derivatives are monocyclic. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Total synthesis of scopine, pseudoscopine, and nor- derivatives
  作者：David E. Justice、John R. Malpass

  DOI：10.1016/0040-4020(96)00693-x

  日期：1996.9

  Scopine and pseudoscopine have been synthesised from cyclohepta-3.5-dienol: the initial 1,4-fuctionalisation of the diene is based on a nitroso-cycloaddition. The use of the N-benzyloxycarbonyl group throughout the scheme allows ultimate reductive deprotection to yield N-methyl or novel NH (nor-) derivatives without damage to the exo-epoxide of the title compounds. Preliminary investigation of nitroso- cycloaddition to 5,6-epoxycyclohepta-1.3-diene is described. Copyright (C) 1996 Elsevier Science Ltd.