5,11,17-Tri-tert-butyl-26,27,28-tris(ethoxy)calix<4>-25-quinone | 146497-53-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17-Tri-tert-butyl-26,27,28-tris(ethoxy)calix<4>-25-quinone
• 英文别名: 5,11,17-Tri-tert-butyl-26,27,28-tris(ethoxy)calix[4]-25-quinone；11,17,23-Tritert-butyl-25,26,27-triethoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,6,9,11,13(27),15(26),16,18,21(25),22-undecaene-5,28-dione
• CAS: 146497-53-2；149496-31-1；149496-32-2
• 化学式: C₄₆H₅₈O₅
• 分子量: 690.964
• InChiKey: IGLPETUXJPLBGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  51
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,11,17-Tri-tert-butyl-26,27,28-tris(ethoxy)calix<4>-25-quinone 以 四氢呋喃 、 乙醇 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 5,11,17-Tri-tert-butyl-22,23-<(methylcarbonyl)oxy>-25-hydroxy-26,27,28-tris(ethoxy)calix<4>arene
  参考文献：
  名称：

  Calixarenes. 32. Reactions of calix[4]quinones

  摘要：

  Calix[4]quinones are readily accessible by direct oxidation of p-tert-butylcalix[4]arenes as mono-, di-, tri- or tetraquinones depending on the number of free phenolic rings in the calixarene. The mono- and diquinones are shown to be useful synthesis intermediates in the following processes: (a) 1,2-carbonyl additions with malononitrile in the presence of secondary amines to yield p-[1-(dialkylamino)-2,2-dicyanovinyl] calixarenes (11) or with malononitrile in the absence of amines to yield p-(1,2,2-tricyanovinyl)calixarenes (9); (b) 1,2-carbonyl addition with pyrrolidine to yield a p-pyrrolidinocalix[4]arene (14); (c) 1,4-conjugate additions with a variety of nucleophiles, including sodio diethyl malonate, acetate, thiourea, p-thiocresol, and mercaptoacetic acid to give the chiral calixarenes 16-2 1.

  DOI：

  10.1021/jo00064a009

文献信息

• Calixarenes. 32. Reactions of calix[4]quinones
  作者：P. Amruta Reddy、C. David Gutsche

  DOI：10.1021/jo00064a009

  日期：1993.6

  Calix[4]quinones are readily accessible by direct oxidation of p-tert-butylcalix[4]arenes as mono-, di-, tri- or tetraquinones depending on the number of free phenolic rings in the calixarene. The mono- and diquinones are shown to be useful synthesis intermediates in the following processes: (a) 1,2-carbonyl additions with malononitrile in the presence of secondary amines to yield p-[1-(dialkylamino)-2,2-dicyanovinyl] calixarenes (11) or with malononitrile in the absence of amines to yield p-(1,2,2-tricyanovinyl)calixarenes (9); (b) 1,2-carbonyl addition with pyrrolidine to yield a p-pyrrolidinocalix[4]arene (14); (c) 1,4-conjugate additions with a variety of nucleophiles, including sodio diethyl malonate, acetate, thiourea, p-thiocresol, and mercaptoacetic acid to give the chiral calixarenes 16-2 1.