5,11,17,23-tetratert-butyl-28-hydrazinylidenepentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),4,9,11,13(27),15(26),16,18,21(25),22-decaene-25,26,27-triol | 147226-42-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,11,17,23-tetratert-butyl-28-hydrazinylidenepentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),4,9,11,13(27),15(26),16,18,21(25),22-decaene-25,26,27-triol
• CAS: 147226-42-4
• 化学式: C₄₄H₆₀N₂O₃
• 分子量: 664.972
• InChiKey: ULHYSHATQOQHAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  49
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  99.1
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetratert-butyl-28-hydrazinylidenepentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),4,9,11,13(27),15(26),16,18,21(25),22-decaene-25,26,27-triol 在 palladium on activated charcoal 作用下， 以 甲苯 为溶剂， 以44%的产率得到monoamino-trihydroxy-p-tert-butylcalix<4>arene
  参考文献：
  名称：

  Spirodienone route for aminodehydroxylation: monoaminotrihydroxy-p-tert-butylcalix[4]arene

  摘要：

  The replacement of one OH group of p-tert-butyl calixarene by an amino group is accomplished via a monospirodienone intermediate.

  DOI：

  10.1021/jo00060a005
• 作为产物：
  描述：

  5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetrahydroxycalix[4]arene monospirodienon 在 sodium hydroxide 、 盐酸肼 作用下， 以 甲醇 为溶剂， 以20%的产率得到5,11,17,23-tetratert-butyl-28-hydrazinylidenepentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),4,9,11,13(27),15(26),16,18,21(25),22-decaene-25,26,27-triol
  参考文献：
  名称：

  Spirodienone route for aminodehydroxylation: monoaminotrihydroxy-p-tert-butylcalix[4]arene

  摘要：

  The replacement of one OH group of p-tert-butyl calixarene by an amino group is accomplished via a monospirodienone intermediate.

  DOI：

  10.1021/jo00060a005

文献信息

• Selective hydroxyl replacement in calixarenes: amino-, azo-, and xanthenocalixarene derivatives.
  作者：Oleg Aleksiuk、Shmuel Cohen、Silvio E. Biali

  DOI：10.1021/ja00143a005

  日期：1995.9

  The synthesis of monoamino-, azo-, and xanthenocalixarenes and dehydroxylated calixarenes via condensation, reduction, or rearrangement of monospirodienone calixarene derivatives is described. Mild oxidation of p-tert-butylcalix[5]arene and p-tert-butylcalix[6]arene yielded their corresponding monospirodienone derivatives 4b and 4c. Monospirodienone 4b was characterized by X-ray crystallography. Reaction of 4b with (2,4-dinitrophenyl)hydrazine gave a (dinitrophenyl)azo derivative (8), which by reaction with HI gave the monoaminotetrahydroxycalix[5]arene 10. Reaction of 4b with hydrazine/base yielded in a Wolff-Kishner-type reaction, the monodehydroxylated calix[5]arene 8. Reaction of 4b with a methanolic solution of hydrazine at room temperature yielded a derivative characterized by X-ray crystallography as a system with an azo bridge (15). Spirodienone 4b rearranges in MeOH/H+, yielding the xanthene derivative 16 as the main product, together with the linear pentamer 17. The larger spirodienone 4c rearranges by treatment with MeOH/H+, yielding the xanthenocalix[6]arene 18. X-ray diffraction of a crystal of 18 grown in MeCN shows that in the crystal the molecules form intermolecular hydrogen-bonded dimers in which the two molecules mutually include each other; i.e., one of the protuberances of each molecule is located in the V-shaped cavity of its neighboring molecule. Molecules 16 and 18 represent the first examples of calixarene systems incorporating a xanthene moiety.