(1α,3β,6α)-3-(Benzyloxy)-7-(ethoxycarbonyl)-7-azabicyclo<4.1.0>heptane

• 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,3β,6α)-3-(Benzyloxy)-7-(ethoxycarbonyl)-7-azabicyclo<4.1.0>heptane
• 英文别名: ethyl (1R,3S,6S)-3-phenylmethoxy-7-azabicyclo[4.1.0]heptane-7-carboxylate
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: HSJBGMWERBSUSB-VVDCQGDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1α,3β,6α)-3-(Benzyloxy)-7-(ethoxycarbonyl)-7-azabicyclo<4.1.0>heptane 在 sodium azide 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 c-4-(Benzyloxy)-t-2-<(ethoxycarbonyl)amino>-r-1-azidocyclohexane
  参考文献：
  名称：

  Regiochemical Control of the Ring Opening of Aziridines by Means of Chelating Processes. Synthesis and Ring-Opening Reactions of cis- and trans-Aziridines Derived from 4-(Benzyloxy)cyclohexene

  摘要：

  The regiochemical outcome of the ring opening of aziridines bearing a polar remote functionality was verified in a conformationally semirigid bicyclic system in which the polar functionality (OBn) is in an homoallylic relationship to the aziridine ring. The couples of diastereoisomeric unactivated cis-3 and trans-4 and activated aziridines cis-5 and -7 and trans-6 and -8 derived from 4-(benzyloxy)-cyclohexene were prepared, and some of their opening reactions were studied. The regioselectivity observed in the opening reactions of the cis derivatives turned out to depend largely on the opening (standard, strongly acidic, or metal-assisted) reaction conditions, thus providing a nice regioalternating process. The results obtained are rationalized by admitting the incursion of chelate bidentate intermediate structures in which the proton or the metal is actively involved.

  DOI：

  10.1021/jo00113a035
• 作为产物：
  描述：

  氯甲酸乙酯 、 (1α,3β,6α)-3-(Benzyloxy)-7-azabicyclo<4.1.0>heptane 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以95%的产率得到(1α,3β,6α)-3-(Benzyloxy)-7-(ethoxycarbonyl)-7-azabicyclo<4.1.0>heptane
  参考文献：
  名称：

  Regiochemical Control of the Ring Opening of Aziridines by Means of Chelating Processes. Synthesis and Ring-Opening Reactions of cis- and trans-Aziridines Derived from 4-(Benzyloxy)cyclohexene

  摘要：

  The regiochemical outcome of the ring opening of aziridines bearing a polar remote functionality was verified in a conformationally semirigid bicyclic system in which the polar functionality (OBn) is in an homoallylic relationship to the aziridine ring. The couples of diastereoisomeric unactivated cis-3 and trans-4 and activated aziridines cis-5 and -7 and trans-6 and -8 derived from 4-(benzyloxy)-cyclohexene were prepared, and some of their opening reactions were studied. The regioselectivity observed in the opening reactions of the cis derivatives turned out to depend largely on the opening (standard, strongly acidic, or metal-assisted) reaction conditions, thus providing a nice regioalternating process. The results obtained are rationalized by admitting the incursion of chelate bidentate intermediate structures in which the proton or the metal is actively involved.

  DOI：

  10.1021/jo00113a035

文献信息

• Regiochemical control of the ring opening of aziridines by means of chelating processes. Part 3: Regioselectivity of the opening reactions with methanol of remote O-substituted regio- and diastereoisomeric activated aziridines under condensed- and gas-phase operating conditions
  作者：Paolo Crotti、Valeria Di Bussolo、Lucilla Favero、Franco Macchia、Gabriele Renzi、Graziella Roselli

  DOI：10.1016/s0040-4020(02)00726-3

  日期：2002.8

  acid methanolysis in the condensed phase (cd-phase) and in the reaction with MeOH in the gas-phase using a gaseous acid (D3+) as the promoting agent. The results obtained in the opening process of the cis diastereoisomers indicate the constant incursion in the gas phase of D+(corresponding to H+)-mediated chelated bidentate species able to modify the regiochemical result found in the methanolysis in

  该非对映异构对活化的氮丙啶的区域化学行为1 - 8从环己烷衍生系统，轴承远程Ó -Functionality，在冷凝相（CD-相）酸甲醇分解被确定并且在该气体中，用MeOH将反应气态酸（D 3 +）作为促进剂的液相。在顺式非对映异构体的打开过程中获得的结果表明，D +（对应于H +）介导的螯合二齿物种在气相中的恒定侵入能够改变cd相在甲醇分解中发现的区域化学结果。