butyl-(1-methylene-but-3-enyl)-ether | 99182-51-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: butyl-(1-methylene-but-3-enyl)-ether
• 英文别名: Butyl-(1-methylen-but-3-enyl)-aether；2-Butoxy-penta-1,4-dien；2-Butoxypenta-1,4-diene
• CAS: 99182-51-1
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: ZBYHULGVKNMBDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  butyl-(1-methylene-but-3-enyl)-ether 在 四氯化锡 、 碳酸氢钠 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 24.5h， 生成 (1R*,6R*,7S*,8S*)-3-aza-1-butoxy-7-methyl-2,4-dioxa-8-phenyltricyclo[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
• 作为产物：
  描述：

  1,2-dibromo-1-butoxyethane 在 氢氧化钾 、 乙醚 作用下， 生成 butyl-(1-methylene-but-3-enyl)-ether
  参考文献：
  名称：

  Schostakowskii; Mamedow, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 3922,3924;engl.Ausg.S.3880,3882

  摘要：

  DOI：

文献信息

• Tandem Inter [4 + 2]/Intra [3 + 2] Cycloadditions. 6. The Bridged Mode
  作者：Scott E. Denmark、Andreas Stolle、Julie A. Dixon、Vito Guagnano

  DOI：10.1021/ja00112a027

  日期：1995.2
• 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：——
• Tandem Inter [4 + 2]/Intra [3 + 2] Cycloadditions of Nitroalkenes. 15. The Bridged Mode (α-Tether)
  作者：Scott E. Denmark、Vito Guagnano、Julie A. Dixon、Andreas Stolle

  DOI：10.1021/jo970686m

  日期：1997.7.1

  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.
• Schostakowskii; Mamedow, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 3922,3924;engl.Ausg.S.3880,3882
  作者：Schostakowskii、Mamedow

  DOI：——

  日期：——