ethyl 1-oxa-spiro[4,5]decan-3-one-2-carboxylate | 341491-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: ethyl 1-oxa-spiro[4,5]decan-3-one-2-carboxylate
• 英文别名: Ethyl 3-oxo-1-oxaspiro[4.5]decane-2-carboxylate
• CAS: 341491-03-0
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: XHDIDRRUHORAPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-oxa-spiro[4,5]decan-3-one-2-carboxylate 在 sodium hydroxide 、 硫酸 作用下， 反应 12.0h， 生成 1-oxaspiro<4.5>decan-3-one
  参考文献：
  名称：

  A short protocol for the synthesis of spirocyclic tetrahydrofurans via intramolecular O–H insertion

  摘要：

  The conversion of cyclic ketones to functionalised spirocyclic tetrahydrofurans via a three-step sequence of acetoacetate ester dianion-aldol reaction, diazo-transfer and carbene O-H insertion is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00097-7
• 作为产物：
  描述：

  ethyl 4-(1-hydroxycyclohexyl)-3-oxobutanoate 在 dirhodium tetraacetate 、 对甲苯磺酰叠氮 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 10.0h， 生成 ethyl 1-oxa-spiro[4,5]decan-3-one-2-carboxylate
  参考文献：
  名称：

  A short protocol for the synthesis of spirocyclic tetrahydrofurans via intramolecular O–H insertion

  摘要：

  The conversion of cyclic ketones to functionalised spirocyclic tetrahydrofurans via a three-step sequence of acetoacetate ester dianion-aldol reaction, diazo-transfer and carbene O-H insertion is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00097-7

文献信息

• Synthesis of oxygen-containing heterocyclic compounds based on the intramolecular O–H insertion and Wolff rearrangement of α-diazocarbonyl compounds
  作者：Mingyi Liao、Suwei Dong、Guisheng Deng、Jianbo Wang

  DOI：10.1016/j.tetlet.2006.05.007

  日期：2006.7

  from β-keto α-diazo carbonyl compound to ketones or α,β-unsaturated compounds were subjected to Rh2(OAc)4-catalyzed and photo-induced diazo decomposition. The Rh2(OAc)4-catalyzed reaction afforded intramolecular O–H insertion products, while the photo-induced reaction gave Wolff rearrangement/intramolecular nucleophilic addition products. The transformations represent new approaches to tetrahydrofuran

  将由β-酮α-重氮羰基化合物衍生的钛（IV）-烯酸酯与酮或α，β-不饱和化合物的加成产物进行Rh 2（OAc）4催化和光诱导的重氮分解。Rh 2（OAc）4催化的反应提供了分子内O–H插入产物，而光诱导的反应产生了Wolff重排/分子内亲核加成产物。该转化代表了四氢呋喃和γ-丁内酯衍生物的新方法。
• A short protocol for the synthesis of spirocyclic tetrahydrofurans via intramolecular O–H insertion
  作者：Keith Jones、Teymour Toutounji

  DOI：10.1016/s0040-4020(01)00097-7

  日期：2001.3

  The conversion of cyclic ketones to functionalised spirocyclic tetrahydrofurans via a three-step sequence of acetoacetate ester dianion-aldol reaction, diazo-transfer and carbene O-H insertion is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

表征谱图