Dimethyl 2,5,8,14,17,20-hexaoxatricyclo[19.3.1.19,13]hexacosa-1(25),9(26),10,12,21,23-hexaene-11,23-dicarboxylate | 148134-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Dimethyl 2,5,8,14,17,20-hexaoxatricyclo[19.3.1.19,13]hexacosa-1(25),9(26),10,12,21,23-hexaene-11,23-dicarboxylate
• CAS: 148134-12-7
• 化学式: C₂₄H₂₈O₁₀
• 分子量: 476.48
• InChiKey: FICCVUZORMUTJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Dimethyl 2,5,8,14,17,20-hexaoxatricyclo[19.3.1.19,13]hexacosa-1(25),9(26),10,12,21,23-hexaene-11,23-dicarboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以93%的产率得到bis(5-hydroxymethyl-1,3-phenylene)-20-crown-6
  参考文献：
  名称：

  通过分子内的Cannizzaro反应 使二取代的芳族冠醚不对称化†

  摘要：

  我们报道了一种高产率的金属模板化Cannizzaro反应，可将70 [98-98]各种类型的对称芳族冠醚二醛[二苯并和双（间亚苯基）]和大小（20-32原子环）转化为酸-醇官能化的冠醚％产率。

  DOI：

  10.1039/c9nj04679h
• 作为产物：
  描述：

  3,5-二羟基苯甲酸甲酯 在 四丁基碘化铵 、 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 122.0h， 生成 Dimethyl 2,5,8,14,17,20-hexaoxatricyclo[19.3.1.19,13]hexacosa-1(25),9(26),10,12,21,23-hexaene-11,23-dicarboxylate
  参考文献：
  名称：

  IMPROVED SYNTHESES OF 20- AND 26-MEMBEREDbis(5-CARBOMETHOXY-1,3-PHENYLENE) CROWN ETHERS

  摘要：

  DOI：

  10.1080/00304949709355194

文献信息

• Syntheses, X-ray Structures, Complexation and Thermal Stability Studies of Bis(5-carbomethoxy-1,3-phenylene)-(3x + 2)-crown-x Compounds
  作者：Yadollah Delaviz、Joseph S. Merola、Michael A. G. Berg、Harry W. Gibson

  DOI：10.1021/jo00108a009

  日期：1995.2

  Bis(5-carbomethoxy-1,3-phenylene)-(3x + 2)-crown-x compounds [x = 6 (3a), x = 8 (3b), and x = 10 (3c)] have been synthesized in one step by reaction of methyl 3,5-dihydroxybenzoate oxybenzoate (1) and the corresponding oligo(ethylene glycol) dichlorides (2a, 2b, and 2c) in the presence of NaH or KH in N,N-dimethylformamide (DMF). The smaller monoester, 5-carbomethoxy-1,3-phenylene-16-crown-5 (4c), was also isolated along with 3c. The X-ray crystal structures of these macrocycles (3b, 3c, and 4c) have been determined. Macrocycle 3b crystallizes in the triclinic space group P-1 with unit cell parameters of a = 8.632(2) Angstrom, b = 10.006(2) Angstrom, c = 11.527(2) Angstrom, alpha = 78.30(3)degrees, beta = 71.98(3)degrees, gamma = 65.00(3)degrees. Macrocycle 3c crystallizes in the triclinic space group P-1 with unit cell parameters of a = 8.911(2) Angstrom, b = 9.497(2) Angstrom, c = 10.140(2) Angstrom, alpha = 93.66(2)degrees, beta = 94.03(1)degrees, gamma = 105.95(1)degrees. Macrocycle 4c crystallizes in the triclinic space group with unit cell parameters of a = 8.748(2) Angstrom, b = 9.163(2) Angstrom, c = 12.025(3) Angstrom, alpha = 74.90(2)degrees, beta = 86.81(2)degrees, gamma = 61.73(2)degrees. The thermal stabilities of these macrocycles and the complexation abilities of the bis(m-phenylene)-32-crown-10 derivatives with methyl viologen bis(hexafluorophosphate) (8) have been examined by H-1 NMR spectroscopy.
• Polyrotaxanes by in situ self threading during polymerization of functional macrocycles. Part 2: Poly(ester crown ether)s
  作者：Harry W Gibson、Devdatt S Nagvekar、Jason Powell、Caiguo Gong、William S Bryant

  DOI：10.1016/s0040-4020(97)00957-5

  日期：1997.11

  Poly(ester crown ether)s were synthesized by direct condensation of bis(5-carboxy-m-phenylene)-(3x + 2)-crown-x, x = 6, 8 and 10 (1a, 1b and 1c) with bisphenols via the Higashi method. The formation of higher molecular weight poly(ester crown ether) 5 from the 32-membered crown ether 1c and bisphenol-A (2a) as compared to polyester 3 from 20-membered crown ether 1a and bisphenol-A, polyester 4 made from the 26-membered crown ether 1b and bisphenol-A (2a) and polyester 6 derived from 32-membered 1c and bis(p-t-butylphenyl)-bis(p-hydroxyphenyl)methane (2b) under identical conditions is believed to be the result of threading (rotaxane formation) in 5 but no or less threading in 3, 4 or 6; indeed polyester 3 provides a control because its macrocyclic component (1a) too small to be threaded, even by a polymethylene chain. Threading in 5 was undetectable through NOESY experiments. However, melt polymerization of bis(5-hydroxymethyl-m-phenylene)-32-crown-10 (7) with sebacoyl chloride (8) gave an insoluble, but swellable elastomeric material 9, a polyrotaxane network, as a result of more extensive in situ threading brought about by hydrogen bonding of the crown ether with the alcohol moieties in the more concentrated medium. (C) 1997 Elsevier Science Ltd.
• IMPROVED SYNTHESES OF 20- AND 26-MEMBERED<i>bis</i>(5-CARBOMETHOXY-1,3-PHENYLENE) CROWN ETHERS
  作者：Devdatt S. Nagvekar、Harry W. Gibson

  DOI：10.1080/00304949709355194

  日期：1997.4
• Desymmetrization of disubstituted aromatic crown ethers<i>via</i>intramolecular Cannizzaro reactions
  作者：Mason A. Rouser、Harry W. Gibson

  DOI：10.1039/c9nj04679h

  日期：——

  We report a high-yielding metal templated Cannizzaro reaction for converting symmetrical aromatic crown ether dialdehydes of various types [dibenzo and bis(meta-phenylene)] and sizes (20–32 atom rings) to acid–alcohol functionalized crown ethers in 70–98% yields.

  我们报道了一种高产率的金属模板化Cannizzaro反应，可将70 [98-98]各种类型的对称芳族冠醚二醛[二苯并和双（间亚苯基）]和大小（20-32原子环）转化为酸-醇官能化的冠醚％产率。