2-[4-(carboxymethyl)-3-oxobutyl]-2-methyl-1,3-dioxane | 190585-44-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-[4-(carboxymethyl)-3-oxobutyl]-2-methyl-1,3-dioxane
• 英文别名: Methyl 5-(2-methyl-1,3-dioxan-2-yl)-3-oxopentanoate
• CAS: 190585-44-5
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: UTUKYGIGVXRXLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[4-(carboxymethyl)-3-oxobutyl]-2-methyl-1,3-dioxane 在 六氟乙酰丙酮化铜的水合物 、 4-羧基苯磺叠氮 、 sodium acetate 、 三乙胺 作用下， 以 乙醇 、 水 、 乙腈 、 苯 为溶剂， 反应 7.0h， 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 在 氢氧化钾 、 对甲苯磺酸 、 N,N'-羰基二咪唑 、 原甲酸三甲酯 作用下， 以 苯 为溶剂， 反应 44.0h， 生成 2-[4-(carboxymethyl)-3-oxobutyl]-2-methyl-1,3-dioxane
  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.