3-[2-(carboxymethyl)ethyl]-3-methyl-1,5-dihydro-3H-2,4-benzodioxepin | 190585-49-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-[2-(carboxymethyl)ethyl]-3-methyl-1,5-dihydro-3H-2,4-benzodioxepin
• 英文别名: Methyl 3-(3-methyl-1,5-dihydro-2,4-benzodioxepin-3-yl)propanoate
• CAS: 190585-49-0
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: QVJVGMYCAIQKAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[2-(carboxymethyl)ethyl]-3-methyl-1,5-dihydro-3H-2,4-benzodioxepin 在 氢氧化钾 、 六氟乙酰丙酮化铜的水合物 、 4-羧基苯磺叠氮 、 对甲苯磺酸 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 乙腈 为溶剂， 反应 42.5h， 生成
  参考文献：
  名称：

  Study of the Rearrangements of Oxonium Ylides Generated from Ketals

  摘要：

  Intramolecular exposure of cyclic ketals to metal carbenoids generates a proposed oxonium ylide intermediate that subsequently rearranges to one of three general products. The product resulting from a 1,2-shift to the ketal carbon is favored by larger ketals that lack radical stabilizing groups. A bridged bicyclic structure is formed by competitive 1,2-shift to the exocyclic carbon of the ketal and is favored by smaller ketal ring sizes that possess radical-stabilizing groups. An alternative beta-elimination pathway can also operate when neither of the 1,2-shift pathways are favored. The enol ether that is formed in this latter pathway rearranges easily to an isomeric dioxene.

  DOI：

  10.1021/jo961896m
• 作为产物：
  描述：

  乙酰丙酸甲酯 、 邻苯二甲醇 在 对甲苯磺酸 、 原甲酸三甲酯 作用下， 以 苯 为溶剂， 反应 12.0h， 以51%的产率得到3-[2-(carboxymethyl)ethyl]-3-methyl-1,5-dihydro-3H-2,4-benzodioxepin
  参考文献：
  名称：

  Study of the Rearrangements of Oxonium Ylides Generated from Ketals

  摘要：

  Intramolecular exposure of cyclic ketals to metal carbenoids generates a proposed oxonium ylide intermediate that subsequently rearranges to one of three general products. The product resulting from a 1,2-shift to the ketal carbon is favored by larger ketals that lack radical stabilizing groups. A bridged bicyclic structure is formed by competitive 1,2-shift to the exocyclic carbon of the ketal and is favored by smaller ketal ring sizes that possess radical-stabilizing groups. An alternative beta-elimination pathway can also operate when neither of the 1,2-shift pathways are favored. The enol ether that is formed in this latter pathway rearranges easily to an isomeric dioxene.

  DOI：

  10.1021/jo961896m

文献信息

• Study of the Rearrangements of Oxonium Ylides Generated from Ketals
  作者：John B. Brogan、Charles K. Zercher、Cary B. Bauer、Robin D. Rogers

  DOI：10.1021/jo961896m

  日期：1997.6.13

  Intramolecular exposure of cyclic ketals to metal carbenoids generates a proposed oxonium ylide intermediate that subsequently rearranges to one of three general products. The product resulting from a 1,2-shift to the ketal carbon is favored by larger ketals that lack radical stabilizing groups. A bridged bicyclic structure is formed by competitive 1,2-shift to the exocyclic carbon of the ketal and is favored by smaller ketal ring sizes that possess radical-stabilizing groups. An alternative beta-elimination pathway can also operate when neither of the 1,2-shift pathways are favored. The enol ether that is formed in this latter pathway rearranges easily to an isomeric dioxene.