6,28-Dimethyl-8,16,18,26-tetraoxa-6,28-diazaheptacyclo[17.12.0.02,15.03,12.04,9.022,31.025,30]hentriaconta-1(19),2(15),3(12),4(9),10,13,20,22(31),23,25(30)-decaene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 6,28-Dimethyl-8,16,18,26-tetraoxa-6,28-diazaheptacyclo[17.12.0.02,15.03,12.04,9.022,31.025,30]hentriaconta-1(19),2(15),3(12),4(9),10,13,20,22(31),23,25(30)-decaene
• 英文别名: 6,28-dimethyl-8,16,18,26-tetraoxa-6,28-diazaheptacyclo[17.12.0.02,15.03,12.04,9.022,31.025,30]hentriaconta-1(19),2(15),3(12),4(9),10,13,20,22(31),23,25(30)-decaene
• 化学式: C₂₇H₂₄N₂O₄
• 分子量: 440.499
• InChiKey: WLTXDOWKWRVNNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  33.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  43.4
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  [1,1'-binaphthalene]-2,2',7,7'-tetraol 在 caesium carbonate 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 101.5h， 生成 6,28-Dimethyl-8,16,18,26-tetraoxa-6,28-diazaheptacyclo[17.12.0.02,15.03,12.04,9.022,31.025,30]hentriaconta-1(19),2(15),3(12),4(9),10,13,20,22(31),23,25(30)-decaene
  参考文献：
  名称：

  Synthesis of enantiomerically pure helicene like bis-oxazines from atropisomeric 7,7′-dihydroxy BINOL: preliminary measurements of the circularly polarized luminescence

  摘要：

  A racemic sample of 2,2',7,7'-tetrahydroxy-1,1'-binaphthyl was resolved with (S)-proline and the separated enantiomers were independently converted to atropisomeric bis-oxazines by aromatic Mannich reaction. These chirally pure oxazines were then converted to the helicene like cyclic ethers. The circularly polarized luminescence (CPL) profile was consistent with the isolation of the targeted helical-like molecules in optically pure form, prepared from the achiral primary amines. The compounds of interest displayed active and opposite CPL activities for each set of the helicene like isomers (P)-/(M)-3 and (P)-/(M)-5. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.108

文献信息

• Synthesis of Chiral Helical 1,3-Oxazines
  作者：Harish R. Talele、Sibaprasad Sahoo、Ashutosh V. Bedekar

  DOI：10.1021/ol301267r

  日期：2012.6.15

  A series of novel 1,3-oxazines were prepared to construct a helical framework. The 1,3-oxazine attached to the phenanthrene unit showed a small bite angle theta (similar to 12 degrees), while the units attached to [4]helicene showed a larger theta (similar to 35 degrees) and exhibited helical isomers at ambient conditions. The diastereomers of the third type of helicene-like bis-oxazine attached to binaphthyl were easily separable and showed good thermal stability. All four diastereomers of bis-helicene were synthesized, and their absolute configuration was established.
• Synthesis of enantiomerically pure helicene like bis-oxazines from atropisomeric 7,7′-dihydroxy BINOL: preliminary measurements of the circularly polarized luminescence
  作者：M. Shyam Sundar、Harish R. Talele、Hemant M. Mande、Ashutosh V. Bedekar、Roberto C. Tovar、Gilles Muller

  DOI：10.1016/j.tetlet.2014.01.108

  日期：2014.3

  A racemic sample of 2,2',7,7'-tetrahydroxy-1,1'-binaphthyl was resolved with (S)-proline and the separated enantiomers were independently converted to atropisomeric bis-oxazines by aromatic Mannich reaction. These chirally pure oxazines were then converted to the helicene like cyclic ethers. The circularly polarized luminescence (CPL) profile was consistent with the isolation of the targeted helical-like molecules in optically pure form, prepared from the achiral primary amines. The compounds of interest displayed active and opposite CPL activities for each set of the helicene like isomers (P)-/(M)-3 and (P)-/(M)-5. (c) 2014 Elsevier Ltd. All rights reserved.