Octadeca-(hydroxymethyl)-30-crown-12-polyacetal | 308790-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: Octadeca-(hydroxymethyl)-30-crown-12-polyacetal
• CAS: 308790-00-3
• 化学式: C₃₆H₇₂O₃₀
• 分子量: 984.95
• InChiKey: KGUOBBLZYKVAGK-FUXDQRKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11.56
• 重原子数：
  66.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  474.9
• 氢给体数：
  18.0
• 氢受体数：
  30.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Octadeca-(hydroxymethyl)-30-crown-12-polyacetal 生成 Octadeca-(acetoxymethyl)-30-crown-12-polyacetal
  参考文献：
  名称：

  Hydroxymethyl-substituted crown acetals with 35-C-14 and 40-C-16 skeletal backbones: synthesis and molecular geometries

  摘要：

  An oxidation/reduction sequence readily converts beta- and gamma -cyclodextrin into hydroxymethyl-substituted crown acetals with 35-C-14 and 40-C-16 skeletal cores. X-Ray analysis of their well crystallizing peracetates reveals the 40-membered ring of the gamma -CD derived octaacetal to mould into an undulated four-loop structure with alternating gauche and anti-conformations of the eight meso-butanetetrol units, the overall shape resembling a four-leaf clover. In the beta -CD derived, 35-membered crown heptaacetal, six of the seven glycolaldehyde/butanetetrol segments are lined up in alternating gauche/anti arrangements with the seventh, uneven unit inserted in gauche orientation. In solution, however, the macrocycles are highly flexible as evidenced by their H-1 and C-13 NMR spectra, which at 300 K show only one set of signals for the respective -CHR-CHR-O-CHR-O- units (R=CH2OH or CH2OAc). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00469-4
• 作为产物：
  描述：

  Octadeca-(acetoxymethyl)-30-crown-12-polyacetal 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以84%的产率得到Octadeca-(hydroxymethyl)-30-crown-12-polyacetal
  参考文献：
  名称：

  Synthesis and Molecular Geometry of an Achiral 30-Crown-12 Polyacetal fromα-Cyclodextrin

  摘要：

  Periodate oxidation of alpha-cyclodestrin followed by borohydride reduction readily provided an octadecahydroxymethyl-substituted 30-crown-12 polyacetal 1, its 30-membered macrocycle being composed of six meso-butanetetrol/glycolaldehyde acetal units, which is, consequently, optically inactive, Its solid-state molecular geometry emerged from the X-ray structural analysis of the well-crystallizing octadeca-acetate 2, which revealed the undulated macrocycle to be molded into three loops with a unique order of succession of the -CHR-CHR-O-CHR-O- units: alternating gauche- and anti-conformations of the meso-butanetetrol portions and consecutive disposition of the glycolaldehyde-acetoxymethyl groups above and below the mean-plane of the macrocycle. In solution, however, as evidenced by H-1- and C-13-NMR spectra, the macrocycle is highly flexible at ambient and higher temperatures, its mobility becoming distinctly restricted only below - 20 degrees C.

  DOI：

  10.1002/1521-3765(20000915)6:18<3366::aid-chem3366>3.0.co;2-9