18,20-dimethyl-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(20),17-diene-19,21-dione | 91202-13-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: 18,20-dimethyl-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(20),17-diene-19,21-dione
• CAS: 91202-13-0
• 化学式: C₁₈H₂₆O₇
• 分子量: 354.4
• InChiKey: MOXCCFNNMJDDDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  25.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2,6-二甲基-1,4-苯二酚 在 盐酸 、 sodium hydroxide 、 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 0.75h， 生成 18,20-dimethyl-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(20),17-diene-19,21-dione
  参考文献：
  名称：

  Synthesis of 1,4-Benzoquinone Derivatives Having Two Side-Armed Polyethers and Crown Ethers, and Their Electrochemical Study in the Presence of Alkali Metal Cations (Na⁺and K⁺)

  摘要：

  制备出了几种具有可还原醌基的冠醚和两种侧臂聚醚。其中一些（7a、7b 和 7d）在电化学还原时对 Na+ 阳离子显示出高度增强的阳离子结合特性。

  DOI：

  10.1246/bcsj.61.3026

文献信息

• Redox-active crown ethers. Electrochemical and electron paramagnetic resonance studies on alkali metal complexes of quinone crown ethers
  作者：Milagros Delgado、Robert E. Wolf、JudithAnn R. Hartman、Gillian McCafferty、Rahmi Yagbasan、Simon C. Rawle、David J. Watkin、Stephen R. Cooper

  DOI：10.1021/ja00049a032

  日期：1992.11

  Structural studies on [M(NCS).(5QC-HQDME)] (M = Li, Na) as well as free 6QC-HQDME and [M(NCS). (6QC-HQDME)] (M = Na, K) (where 5QC-HQDME is 15,17-dimethyl-16,18-dimethoxy-3,6,9,12-tetraoxabicyclo[12.3.1]octadeca(1,14,16)triene, and 6QC-HQDME is 15,17-dimethyl-16,18-dimethoxy-3,6,9,12,15-pentaoxabicyclo[15.3.1]heneico(1,14,16)triene) show that in all cases the metal ion binds to the anisole oxygen atom in the 1-position. Only in the case of [K(NCS).(6QC-HQDME)] do both benzylic O atoms bind to the metal ion; in the other complexes only one of these O atoms interacts with M+. In each complex all of the non-benzylic crown O atoms coordinate. These results indicate that the benzylic O atoms contribute suboptimally to complexation. Crystallographic data are as follows: [Li(NCS). (5QC-HQDME)], monoclinic, C19H28NO6SLi, space group P2(1)/n, a = 14.103 (4) angstrom, b = 8.493 (4) angstrom, c = 19.128 (8) angstrom, beta = 108.70 (9)-degrees, Z = 4; [Na(NCS).(5QC-HQDME)], monoclinic, C19H28NO6SNa, space group P2(1)/c, a = 10.182 (4) angstrom, b = 8.601 (1) angstrom, c = 25.631 (3) angstrom, beta = 97.29 (3)-degrees, Z = 4; 6QC-HQDME, orthohombic, C20H32O7, space group P2(1)2(1)2(1), a = 8.195 (1) angstrom, b = 11.541 (1) angstrom, c = 22.449 (3) angstrom, Z = 4; [Na(NCS).(6QC-HQDME)].MeCN, monoclinic, C23H35N2O7SNa, space group P2(1)/c, a = 11.308 (1) angstrom, b = 14.521 (2) angstrom, c = 16.440 (4) angstrom, beta = 91.56 (1)-degrees, Z = 4; [K(NCS).(6QC-HQDME)], monoclinic, C21H32NO7SK, space group P2(1)/c, a = 17.377 (3) angstrom, b = 10.600 (2) angstrom, c = 27.538 (7) angstrom, beta = 102.41 (3)-degrees, Z = 8. Electrochemical and EPR studies show that redox-active crown ethers incorporating quinone groups successfully couple ion binding by the crown ether to the redox state of the quinone group. Alkali metal ions cause potential shifts that establish-differential redox-induced complexation that qualitatively and quantitatively differs from ion-pairing effects. They also perturb the EPR hyperfine splittings in the semiquinone moieties in a characteristic fashion, as well as in one case giving rise to Na-23 superhyperfine splitting.
• TOGO, HIDEO;HASHIMOTO, KIICHI;MORIHASHI, KENJI;KIKUCHI, OSAMU, BULL. CHEM. SOC. JAP., 61,(1988) N 8, C. 3026-3028
  作者：TOGO, HIDEO、HASHIMOTO, KIICHI、MORIHASHI, KENJI、KIKUCHI, OSAMU

  DOI：——

  日期：——