(1R,6R,7S,8S)-3-aza-7-methyl-2,4-dioxa-8-phenyl-1-[(1S,2R)-(2-phenylcyclohexyl)oxy]tricyclo[4.3.1.0^3,7]decane | 191937-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (1R,6R,7S,8S)-3-aza-7-methyl-2,4-dioxa-8-phenyl-1-[(1S,2R)-(2-phenylcyclohexyl)oxy]tricyclo[4.3.1.0^3,7]decane
• 英文别名: (1R,6R,7S,8S)-7-methyl-8-phenyl-1-[(1S,2R)-2-phenylcyclohexyl]oxy-2,4-dioxa-3-azatricyclo[4.3.1.03,7]decane
• CAS: 191937-78-7
• 化学式: C₂₆H₃₁NO₃
• 分子量: 405.537
• InChiKey: HMPBUTSCELTSCK-NPSPJNBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,6R,7S,8S)-3-aza-7-methyl-2,4-dioxa-8-phenyl-1-[(1S,2R)-(2-phenylcyclohexyl)oxy]tricyclo[4.3.1.0^3,7]decane 在 镍 吡啶 、 氢气 、 potassium carbonate 作用下， 生成 rel-(1R,2S,3S)-2-acetylamino-2-methyl-5-oxo-3-phenylcyclohexanemethyl acetate
  参考文献：
  名称：

  Tandem Inter [4 + 2]/Intra [3 + 2] Cycloadditions of Nitroalkenes. 15. The Bridged Mode (α-Tether)

  摘要：

  A new variant of the tandem inter [4 + 2]/intra [3 + 2] cycloaddition of nitroalkenes is described in detail. The scope and limitations of the bridged mode tandem cycloaddition in which the diene and dienophile are part of the same molecule are documented. Simple 1,4-pentadienes as well as 2-alkoxy-1,4-pentadienes can function effectively as dienophile and dipolarophile combinations with excellent chemical selectivity and regio- and diastereoselectivities. Hydrogenation of the bridged nitroso acetals produces aminocyclohexanemethanol derivatives in high diastereo- and enantioselectivities. Further, insights into the mechanistic aspects of the Raney nickel promoted hydrogenation are reported. An intriguing influence of the nitro olefin alpha-substituent on the diastereoselectivity in the [4 + 2] cycloaddition has been documented. The reactivity of the alpha-chlorosubstituted nitroalkene 26 as the heterodiene in the Diels-Alder reaction is assayed, and the use of the chlorine atom as a hydrogen surrogate is described.

  DOI：

  10.1021/jo970686m
• 作为产物：
  描述：

  苯,(2-硝基-1-丙烯基)-,(E)- 在 四氯化锡 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 26.17h， 生成 (1R,6R,7S,8S)-3-aza-7-methyl-2,4-dioxa-8-phenyl-1-[(1S,2R)-(2-phenylcyclohexyl)oxy]tricyclo[4.3.1.0^3,7]decane
  参考文献：
  名称：

  Tandem Inter [4 + 2]/Intra [3 + 2] Cycloadditions of Nitroalkenes. 15. The Bridged Mode (α-Tether)

  摘要：

  A new variant of the tandem inter [4 + 2]/intra [3 + 2] cycloaddition of nitroalkenes is described in detail. The scope and limitations of the bridged mode tandem cycloaddition in which the diene and dienophile are part of the same molecule are documented. Simple 1,4-pentadienes as well as 2-alkoxy-1,4-pentadienes can function effectively as dienophile and dipolarophile combinations with excellent chemical selectivity and regio- and diastereoselectivities. Hydrogenation of the bridged nitroso acetals produces aminocyclohexanemethanol derivatives in high diastereo- and enantioselectivities. Further, insights into the mechanistic aspects of the Raney nickel promoted hydrogenation are reported. An intriguing influence of the nitro olefin alpha-substituent on the diastereoselectivity in the [4 + 2] cycloaddition has been documented. The reactivity of the alpha-chlorosubstituted nitroalkene 26 as the heterodiene in the Diels-Alder reaction is assayed, and the use of the chlorine atom as a hydrogen surrogate is described.

  DOI：

  10.1021/jo970686m

文献信息

• Denmark Scott E., Stolle Andreas, Dixon Julie A., Guagnano Vito, J. Amer. Chem. Soc., 117 (1995) N 7, S 2100-2101
  作者：Denmark Scott E., Stolle Andreas, Dixon Julie A., Guagnano Vito

  DOI：——

  日期：——