1α-chloro-2β,3β-epoxy-4β-<(benzyloxycarbonyl)amino>-6α-<(t-butyldimethylsilyl)oxy>cycloheptane

• 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: 1α-chloro-2β,3β-epoxy-4β-<(benzyloxycarbonyl)amino>-6α-<(t-butyldimethylsilyl)oxy>cycloheptane
• 化学式: C₂₁H₃₂ClNO₄Si
• 分子量: 426.028
• InChiKey: MHWBYAVKWAMLLX-BRIYLRKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60.09
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1α-chloro-2β,3β-epoxy-4β-<(benzyloxycarbonyl)amino>-6α-<(t-butyldimethylsilyl)oxy>cycloheptane 在 lithium aluminium tetrahydride 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醚 为溶剂， 反应 23.0h， 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：

  环庚-3,5-二烯-1-醇 在 咪唑 、 正丁基锂 、 sodium amalgam 、 tetramethylammonium metaperiodate 、 间氯过氧苯甲酸 、 sodium phosphate 、 lithium chloride 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.17h， 生成 1α-chloro-2β,3β-epoxy-4β-<(benzyloxycarbonyl)amino>-6α-<(t-butyldimethylsilyl)oxy>cycloheptane
  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

• Exo- and endo-6-hydroxy- and 6,7-epoxytropanes; Total synthesis of scopine, pseudoscopine, and nor-derivatives
  作者：David E Justice、John R Malpass

  DOI：10.1016/0040-4039(95)00836-2

  日期：1995.6

  Novel endo- 6,7-epoxy-8-azabicyclo[3.2.1]octane derivatives and the corresponding exo-analogues have been synthesized and show substantially different reactivity; the resistance of the exo-epoxides to ring opening during hydride reduction and catalytic hydrogenolysis is exploited in a total synthesis of scopine, pseudoscopine, and nor -derivatives.

  已经合成了新型的内-6,7-环氧-8-氮杂双环[3.2.1]辛烷衍生物和相应的外-类似物，并显示出显着不同的反应性。在碱，假pseudo碱和正-衍生物的全合成中，利用了外环氧化合物在氢化物还原和催化氢解过程中对开环的抗性。
• 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.