β.-核-六吡喃糖,1,6-脱水-2-O-(2-氰基苯基)甲基-3-脱氧-4-O-甲基- | 140116-64-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: β.-核-六吡喃糖,1,6-脱水-2-O-(2-氰基苯基)甲基-3-脱氧-4-O-甲基-
• 英文名称: 5,5-Dimethyl-2-isopropyl-1-pyrroline N-oxide
• 英文别名: 2,2-Dimethyl-1-oxido-5-propan-2-yl-3,4-dihydropyrrol-1-ium
• CAS: 140116-64-9
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: ZPUJKMIRZKSQMR-UHFFFAOYSA-N

物化性质

• 沸点：
  229.0±23.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5,5-二甲基-1-吡咯啉-N-氧化物	5,5-Dimethyl-1-pyrroline N-oxide	3317-61-1	C6H11NO	113.159

反应信息

• 作为反应物：
  描述：

  β.-核-六吡喃糖,1,6-脱水-2-O-(2-氰基苯基)甲基-3-脱氧-4-O-甲基- 、 丙炔酸甲酯 以 乙醚 为溶剂， 反应 72.0h， 生成 5-Isopropyl-4-methoxycarbonyl-8,8-dimethyl-2-oxa-1-azabicyclo<3.3>octene-3 、 5-Isopropyl-3-methoxycarbonyl-8,8-dimethyl-2-oxa-1-azabicyclo<3.3>octene-3
  参考文献：
  名称：

  Steric effects on regioselectivity in 1.3-Dipolar cycloaddition of C,N-dialyl nitrones with acceptor-substituted alkynes

  摘要：

  The 1.3 dipolar cycloaddition of alkynes 4-6 with acyclic nitrones 1-3, 23 and 24 as well as with cyclic nitrones 27 is studied. As was found for the reaction of the aldonitrones 1-3 an increased portion of 5-regioisomers is formed with increasing steric demand of either of the two substituents, the C-alkyl substituent R2 and the N-alkyl substituent R1. Thus the conclusion is drawn that cycloaddition of 1-3 proceeds not only via transition states arising from Z-nitrones but also via transition states developing from E-nitrones, although in the ground-state the Z-isomer is favored to a considerable extent. In this context steric destabilization of the transition states is discussed qualitatively.

  DOI：

  10.1016/s0040-4020(01)88127-8
• 作为产物：
  描述：

  5,5-二甲基-1-吡咯啉-N-氧化物 在 Cu-acetate 、 氨 、 氧气 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 0.5h， 生成 β.-核-六吡喃糖,1,6-脱水-2-O-(2-氰基苯基)甲基-3-脱氧-4-O-甲基-
  参考文献：
  名称：

  Steric effects on regioselectivity in 1.3-Dipolar cycloaddition of C,N-dialyl nitrones with acceptor-substituted alkynes

  摘要：

  The 1.3 dipolar cycloaddition of alkynes 4-6 with acyclic nitrones 1-3, 23 and 24 as well as with cyclic nitrones 27 is studied. As was found for the reaction of the aldonitrones 1-3 an increased portion of 5-regioisomers is formed with increasing steric demand of either of the two substituents, the C-alkyl substituent R2 and the N-alkyl substituent R1. Thus the conclusion is drawn that cycloaddition of 1-3 proceeds not only via transition states arising from Z-nitrones but also via transition states developing from E-nitrones, although in the ground-state the Z-isomer is favored to a considerable extent. In this context steric destabilization of the transition states is discussed qualitatively.

  DOI：

  10.1016/s0040-4020(01)88127-8

文献信息

• Steric effects on regioselectivity in 1.3-Dipolar cycloaddition of C,N-dialyl nitrones with acceptor-substituted alkynes
  作者：Hans Günter Aurich、Michael Franzke、Hans Peter Kesselheim、Markus Rohr

  DOI：10.1016/s0040-4020(01)88127-8

  日期：——

  The 1.3 dipolar cycloaddition of alkynes 4-6 with acyclic nitrones 1-3, 23 and 24 as well as with cyclic nitrones 27 is studied. As was found for the reaction of the aldonitrones 1-3 an increased portion of 5-regioisomers is formed with increasing steric demand of either of the two substituents, the C-alkyl substituent R2 and the N-alkyl substituent R1. Thus the conclusion is drawn that cycloaddition of 1-3 proceeds not only via transition states arising from Z-nitrones but also via transition states developing from E-nitrones, although in the ground-state the Z-isomer is favored to a considerable extent. In this context steric destabilization of the transition states is discussed qualitatively.