(R,cR)-5,11,17,23-tetra(tert-butyl)-25,26-dihydroxy-28-methoxy-27-N-(1'-phenylethyl-)-aminocarbonylmethoxycalix[4]arene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R,cR)-5,11,17,23-tetra(tert-butyl)-25,26-dihydroxy-28-methoxy-27-N-(1'-phenylethyl-)-aminocarbonylmethoxycalix[4]arene
• 英文别名: N-[(1R)-1-phenylethyl]-2-[(5,11,17,23-tetratert-butyl-26,27-dihydroxy-28-methoxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl)oxy]acetamide
• 化学式: C₅₅H₆₉NO₅
• 分子量: 824.157
• InChiKey: ZMMKNRDHCJARGW-MGBGTMOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.8
• 重原子数：
  61
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R,cR)-5,11,17,23-tetra(tert-butyl)-25,26-dihydroxy-28-methoxy-27-N-(1'-phenylethyl-)-aminocarbonylmethoxycalix[4]arene 在 硫酸 、 sodium hydroxide 、 barium(II) hydroxide 作用下， 以 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 142.0h， 生成 (cR)-5,11,17,23-tetra(tert-butyl)-27-butoxy-26-methoxy-28-propoxy-25-methoxycarbonylmethylenoxycalix[4]arene
  参考文献：
  名称：

  Stereoselective synthesis of six stereoisomers of inherently chiral methoxy-propoxy-butoxy-methoxycarbonylmethoxy-tert-butylcalix[4]arene

  摘要：

  All six possible stereoisomers of calix[4]arenes with four different substituents on the lower rim of the macrocycle have been synthesized by stepwise alkylation of the hydroxyl groups of tert-butylcalix[4]arene using (R)- or (S)-1-phenylethylamide groups as chiral auxiliaries. They form three enantiomeric pairs, as confirmed by the values of their specific rotation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.06.055
• 作为产物：
  描述：

  N-(1-phenylethyl)-2-[(5,11,17,23-tetratert-butyl-26,27-dihydroxy-28-methoxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl)oxy]acetamide 在 N,N'-二环己基碳二亚胺 、 barium(II) hydroxide 作用下， 以 二甲基亚砜 、 乙酸乙酯 、 正丁醇 为溶剂， 反应 34.0h， 生成 (R,cR)-5,11,17,23-tetra(tert-butyl)-25,26-dihydroxy-28-methoxy-27-N-(1'-phenylethyl-)-aminocarbonylmethoxycalix[4]arene
  参考文献：
  名称：

  Stereoselective synthesis of six stereoisomers of inherently chiral methoxy-propoxy-butoxy-methoxycarbonylmethoxy-tert-butylcalix[4]arene

  摘要：

  All six possible stereoisomers of calix[4]arenes with four different substituents on the lower rim of the macrocycle have been synthesized by stepwise alkylation of the hydroxyl groups of tert-butylcalix[4]arene using (R)- or (S)-1-phenylethylamide groups as chiral auxiliaries. They form three enantiomeric pairs, as confirmed by the values of their specific rotation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.06.055

文献信息

• Stereoselective synthesis of six stereoisomers of inherently chiral methoxy-propoxy-butoxy-methoxycarbonylmethoxy-tert-butylcalix[4]arene
  作者：Kirill A. Polischuk、Oleksandr A. Yesypenko、Alexander B. Rozhenko、Vladimir V. Pirozhenko、Yuriy A. Salimov、Valentina V. Ischenko、Vyacheslav I. Boyko、Volodymyr P. Khilya、Vitaly I. Kalchenko

  DOI：10.1016/j.tetlet.2015.06.055

  日期：2015.8

  All six possible stereoisomers of calix[4]arenes with four different substituents on the lower rim of the macrocycle have been synthesized by stepwise alkylation of the hydroxyl groups of tert-butylcalix[4]arene using (R)- or (S)-1-phenylethylamide groups as chiral auxiliaries. They form three enantiomeric pairs, as confirmed by the values of their specific rotation. (C) 2015 Elsevier Ltd. All rights reserved.