N-Acetyl-N-(phenylmethyl)-6-(3,5-dimethyl-4-hydroxyphenyl)hex-1-enamine | 149777-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-Acetyl-N-(phenylmethyl)-6-(3,5-dimethyl-4-hydroxyphenyl)hex-1-enamine
• 英文别名: N-benzyl-N-[(E)-6-(4-hydroxy-3,5-dimethylphenyl)hex-1-enyl]acetamide
• CAS: 149777-43-5
• 化学式: C₂₃H₂₉NO₂
• 分子量: 351.489
• InChiKey: AQMUBYDRRFELAS-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Acetyl-N-(phenylmethyl)-6-(3,5-dimethyl-4-hydroxyphenyl)hex-1-enamine 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 silver(l) oxide 作用下， 以 乙醚 、 二氯甲烷 、 二氯甲烷-D2 为溶剂， 反应 3.59h， 生成 (+/-)-(3aR^*,8S^*,8aR^*)-5,7-Dimethyl-8--6-hydroxy-1,2,3,3a,8,8a-hexahydrocyclopentindene
  参考文献：
  名称：

  Intramolecular formal [3 + 2] cycloaddition of alkenes and benzylic cations. Stereoselective synthesis of 1,2,3,4,4a,9a-hexahydrofluorenes

  摘要：

  The Lewis acid-promoted intramolecular formal [3 + 2]-atom 'cycloaddition' of alkenes with benzylic cations derived from benzylic alcohols and quinone methides affords products in good yield and with remarkable stereoselectivity. Benzylic alcohol 20 affords hexahydrofluorene 36 with three new stereogenic centers in 73% yield as a 10:1 mixture of diastereomers. The scope and limitations of these reactions were explored by varying the substitution pattern on the benzylic cation, the cyclization initiators, and the alkene terminators.

  DOI：

  10.1021/jo00071a024
• 作为产物：
  描述：

  6-<4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethylphenyl>hexanal 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 magnesium sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 4.08h， 生成 N-Acetyl-N-(phenylmethyl)-6-(3,5-dimethyl-4-hydroxyphenyl)hex-1-enamine
  参考文献：
  名称：

  Intramolecular formal [3 + 2] cycloaddition of alkenes and benzylic cations. Stereoselective synthesis of 1,2,3,4,4a,9a-hexahydrofluorenes

  摘要：

  The Lewis acid-promoted intramolecular formal [3 + 2]-atom 'cycloaddition' of alkenes with benzylic cations derived from benzylic alcohols and quinone methides affords products in good yield and with remarkable stereoselectivity. Benzylic alcohol 20 affords hexahydrofluorene 36 with three new stereogenic centers in 73% yield as a 10:1 mixture of diastereomers. The scope and limitations of these reactions were explored by varying the substitution pattern on the benzylic cation, the cyclization initiators, and the alkene terminators.

  DOI：

  10.1021/jo00071a024

文献信息

• Cyclization reactions terminated by enamides and enecarbamates
  作者：Steven R. Angle、Rogelio P. Frutos

  DOI：10.1039/c39930000171

  日期：——

  The formation of five- and six-membered rings using cyclization reactions terminated by enamides and enecarbamates is described.

  介绍了利用以烯酰胺和烯碳酰胺酸盐为末端的环化反应形成五元和六元环的过程。
• Intramolecular formal [3 + 2] cycloaddition of alkenes and benzylic cations. Stereoselective synthesis of 1,2,3,4,4a,9a-hexahydrofluorenes
  作者：Steven R. Angle、Rogelio P. Frutos

  DOI：10.1021/jo00071a024

  日期：1993.9

  The Lewis acid-promoted intramolecular formal [3 + 2]-atom 'cycloaddition' of alkenes with benzylic cations derived from benzylic alcohols and quinone methides affords products in good yield and with remarkable stereoselectivity. Benzylic alcohol 20 affords hexahydrofluorene 36 with three new stereogenic centers in 73% yield as a 10:1 mixture of diastereomers. The scope and limitations of these reactions were explored by varying the substitution pattern on the benzylic cation, the cyclization initiators, and the alkene terminators.