6-氯-2,5-二甲基-3,4-二氢-2H-吡喃-2-甲酰氯 | 97424-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 6-氯-2,5-二甲基-3,4-二氢-2H-吡喃-2-甲酰氯
• 英文名称: 6-chloro-3,4-dihydro-2,5-dimethyl-2H-pyran-2-carbonyl chloride
• 英文别名: 6-chloro-2,5-dimethyl-3,4-dihydro-2H-pyran-2-carbonyl chloride；6-chloro-2,5-dimethyl-3,4-dihydropyran-2-carbonyl chloride
• CAS: 97424-78-7
• 化学式: C₈H₁₀Cl₂O₂
• 分子量: 209.072
• InChiKey: ASPQYZAUAABCLE-UHFFFAOYSA-N

物化性质

• 沸点：
  258.8±40.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-氯-2,5-二甲基-3,4-二氢-2H-吡喃-2-甲酰氯 以 氘代甲苯 为溶剂， 反应 4.0h， 生成 甲基丙烯酰氯
  参考文献：
  名称：

  Methacryloyl chloride dimers: from structure elucidation to a manifold of chemical transformations

  摘要：

  We report the isolation and elucidation of structure, formation mechanisms, and reactivity of elusive methacryloyl chloride dimers. Upon standing of a sample of methacryloyl chloride (1) for prolonged periods of time dimer 3 forms via oxa-Diels-Alder reaction even at low temperatures. If traces of a Lewis acid are present, dimer 3 isomerizes into a mixture of 2-oxo-cyclopentanecarbonyl chlorides 4, 14, and traces of 5, with a relative ratio that depends on the nature of the Lewis acid and reaction time. Dimer 3 can also be separated and isolated by vacuum distillation and selectively converted into derivatives of 2,5-dimethyl-2-hydroxyadipic acid, as well as into the compound 14 by treating with a catalytic amount of titanium tetrachloride. Additionally, based on the study, suggestions on purification and handling of methacryloyl chloride are proposed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.07.019
• 作为产物：
  描述：

  甲基丙烯酰氯 以 neat (no solvent) 为溶剂， 反应 1461.0h， 以50%的产率得到6-氯-2,5-二甲基-3,4-二氢-2H-吡喃-2-甲酰氯
  参考文献：
  名称：

  Methacryloyl chloride dimers: from structure elucidation to a manifold of chemical transformations

  摘要：

  We report the isolation and elucidation of structure, formation mechanisms, and reactivity of elusive methacryloyl chloride dimers. Upon standing of a sample of methacryloyl chloride (1) for prolonged periods of time dimer 3 forms via oxa-Diels-Alder reaction even at low temperatures. If traces of a Lewis acid are present, dimer 3 isomerizes into a mixture of 2-oxo-cyclopentanecarbonyl chlorides 4, 14, and traces of 5, with a relative ratio that depends on the nature of the Lewis acid and reaction time. Dimer 3 can also be separated and isolated by vacuum distillation and selectively converted into derivatives of 2,5-dimethyl-2-hydroxyadipic acid, as well as into the compound 14 by treating with a catalytic amount of titanium tetrachloride. Additionally, based on the study, suggestions on purification and handling of methacryloyl chloride are proposed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.07.019

文献信息

• FISCHER, W.;BELLUS, D.;ALDER, A.;FRANCOTTE, E.;ROLOFF, A., CHIMIA, 1985, 39, N 1, 19-20
  作者：FISCHER, W.、BELLUS, D.、ALDER, A.、FRANCOTTE, E.、ROLOFF, A.

  DOI：——

  日期：——
• Methacryloyl chloride dimers: from structure elucidation to a manifold of chemical transformations
  作者：Jonas Warneke、Ziyan Wang、Matthias Zeller、Dieter Leibfritz、Markus Plaumann、Vladimir A. Azov

  DOI：10.1016/j.tet.2014.07.019

  日期：2014.9

  We report the isolation and elucidation of structure, formation mechanisms, and reactivity of elusive methacryloyl chloride dimers. Upon standing of a sample of methacryloyl chloride (1) for prolonged periods of time dimer 3 forms via oxa-Diels-Alder reaction even at low temperatures. If traces of a Lewis acid are present, dimer 3 isomerizes into a mixture of 2-oxo-cyclopentanecarbonyl chlorides 4, 14, and traces of 5, with a relative ratio that depends on the nature of the Lewis acid and reaction time. Dimer 3 can also be separated and isolated by vacuum distillation and selectively converted into derivatives of 2,5-dimethyl-2-hydroxyadipic acid, as well as into the compound 14 by treating with a catalytic amount of titanium tetrachloride. Additionally, based on the study, suggestions on purification and handling of methacryloyl chloride are proposed. (C) 2014 Elsevier Ltd. All rights reserved.

表征谱图