1,2-bis(2,6-dimethylphenoxy)ethane | 26802-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2-bis(2,6-dimethylphenoxy)ethane
• 英文别名: 1,2-Di-(2,6-xylyloxy)-ethan；2-[2-(2,6-dimethylphenoxy)ethoxy]-1,3-dimethylbenzene
• CAS: 26802-57-3
• 化学式: C₁₈H₂₂O₂
• 分子量: 270.371
• InChiKey: HNDHABQSUKCTMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,2-bis(2,6-dimethylphenoxy)ethane 在 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醇 、 苯 为溶剂， 反应 15.0h， 生成 9,18-(ethylenedioxy)-2,11-dithia<3.3>metacyclophane
  参考文献：
  名称：

  Synthesis and conformational study of 9,18-(ethylenedioxy)-2,11-dithia[3.3]metacyclophane: the propelling behavior of the three bridges in a [3.4.3](1,2,3)cyclophane

  摘要：

  A general approach which involved first the introduction of the central oxy or dioxy bridge and subsequent intramolecular coupling reactions to form the two thia bridges was employed in the syntheses of the 1,2,3-triply bridged cyclophanes 2, 3, and 4. The attempted routes to potential precursors of 2 were unsuccessful while the tetrabromide 16 could be synthesized. Intramolecular cyclizations of the latter, however, failed to yield 4, possibly due to unfavorable stereochemistry of the intermediate leading to the second intramolecular coupling reaction. The tetrabromide 18, with a central bridge of an appropriate length, successfully led to the formation of 3. The conformational behavior of 3 was analyzed by dynamic H-1 NMR spectroscopy. The ethylenedioxy bridge is believed to adopt the symmetrical ''boat'' conformation. All three bridges, however, undergo unrestricted pseudorotation, represented by free conformational interconversion 3b reversible 3c, at room temperature. A relatively frozen conformation 3b (3c) was observed at the low-temperature limit. Flipping processes of the ethylenedioxy bridge and the two thia bridges are found to be interdependent, resulting in an overall propelling process with a common conformational barrier estimated at ca. 45 kJ mol-1.

  DOI：

  10.1021/jo00001a050
• 作为产物：
  描述：

  2,6-二甲基苯酚 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 1,2-bis(2,6-dimethylphenoxy)ethane
  参考文献：
  名称：

  Synthesis and conformational study of 9,18-(ethylenedioxy)-2,11-dithia[3.3]metacyclophane: the propelling behavior of the three bridges in a [3.4.3](1,2,3)cyclophane

  摘要：

  A general approach which involved first the introduction of the central oxy or dioxy bridge and subsequent intramolecular coupling reactions to form the two thia bridges was employed in the syntheses of the 1,2,3-triply bridged cyclophanes 2, 3, and 4. The attempted routes to potential precursors of 2 were unsuccessful while the tetrabromide 16 could be synthesized. Intramolecular cyclizations of the latter, however, failed to yield 4, possibly due to unfavorable stereochemistry of the intermediate leading to the second intramolecular coupling reaction. The tetrabromide 18, with a central bridge of an appropriate length, successfully led to the formation of 3. The conformational behavior of 3 was analyzed by dynamic H-1 NMR spectroscopy. The ethylenedioxy bridge is believed to adopt the symmetrical ''boat'' conformation. All three bridges, however, undergo unrestricted pseudorotation, represented by free conformational interconversion 3b reversible 3c, at room temperature. A relatively frozen conformation 3b (3c) was observed at the low-temperature limit. Flipping processes of the ethylenedioxy bridge and the two thia bridges are found to be interdependent, resulting in an overall propelling process with a common conformational barrier estimated at ca. 45 kJ mol-1.

  DOI：

  10.1021/jo00001a050

文献信息

• Phosphocholine 2, 6-xylyl ether bromide: proton-phosphorus coupling constants and preliminary pharmacological assessment
  作者：E R Clark、I E Hughes

  DOI：10.1111/j.2042-7158.1970.tb08519.x

  日期：2011.4.12

  Phosphocholine 2, 6-xylyl ether bromide [PPP-trimethyl-2-(2, 6-xylyloxy)ethylphosphonium bromide], has been synthesized by reacting 2-(2, 6-xylyloxy)ethyl bromide with a solution of trimethyl-phosphine in phenol, but ethylenebis(trimethylphosphonium bromide), 1, 2-di(2, 6-xylyloxy)ethane and 2, 6-xylenol were the only reaction products identified when ether was used as solvent. The 2JPH and 3JPH coupling constants for these phosphonium salts have been determined. Although the phosphocholine xylyl ether blocks the Finkleman preparation in concentrations of 2–3 × 10−5 g/ml, this blockade does not have all the characteristics of the adrenergic neuron blockade produced by xylocholine.

  通过将2-(2,6-二甲氧基苯氧基)乙基溴与苯酚中的三甲基膦溶液反应，合成了磷酸胆碱2,6-二甲氧基苯醚溴化物[PPP-三甲基-2-(2,6-二甲氧基苯氧基)乙基磷酸胆碱溴化物]，但当以醚作为溶剂时，乙二醇二(三甲基溴化磷)酸酯、1,2-二(2,6-二甲氧基苯氧基)乙烷和2,6-二甲苯酚是唯一确定的反应产物。已确定了这些磷酸胆碱盐的2JPH和3JPH耦合常数。虽然磷酸胆碱二甲氧基苯醚在2-3×10-5 g/ml的浓度下阻断了Finkleman制剂，但这种阻断并没有所有由xylocholine产生的肾上腺素能神经元阻断的特征。

• LAI, YEE-HING;TAN, CHIN-WEE, J. ORG. CHEM., 56,(1991) N, C. 264-267
  作者：LAI, YEE-HING、TAN, CHIN-WEE

  DOI：——

  日期：——