2,2-dimethyl-5-(4-pentenyl)-1,3-dioxane-4,6-dione | 120875-51-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2-dimethyl-5-(4-pentenyl)-1,3-dioxane-4,6-dione
• 英文别名: 2,2-dimethyl-5-(pent-4-en-1-yl)-1,3-dioxane-4,6-dione；2,2-Dimethyl-5-pent-4-enyl-1,3-dioxane-4,6-dione
• CAS: 120875-51-6
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: AFHUWCRYLHLCGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  3-cyclohexen-1-ol 、 2,2-dimethyl-5-(4-pentenyl)-1,3-dioxane-4,6-dione 在 C₇₂H₆₀O₁₂P₄Pd 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Chain-Walking Strategy for Organic Synthesis: Catalytic Cycloisomerization of 1,n-Dienes

  摘要：

  The catalytic construction of carbon-carbon bonds in small organic molecules via chain walking is described. Catalytic cycloisomerization of 1,n-dienes via chain walking was achieved using a palladium-1,10-phenanthroline catalyst to form five-membered-ring products. By means of a cycloisomerization/hydrogenation protocol, 1,7- to 1,14-dienes were selectively converted to bicyclo[4.3.0]nonane derivatives. The use of chain walking provides a new method in organic synthesis to functionalize unreactive carbon-hydrogen bonds by letting the catalyst look for preferable bond-forming sites by moving around on the substrate.

  DOI：

  10.1021/ja308377u
• 作为产物：
  描述：

  dimethyl 2-(pent-4'-enyl)malonate 在 乙醇 、 硫酸 、 乙酸酐 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 40.0h， 生成 2,2-dimethyl-5-(4-pentenyl)-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Chain-Walking Strategy for Organic Synthesis: Catalytic Cycloisomerization of 1,n-Dienes

  摘要：

  The catalytic construction of carbon-carbon bonds in small organic molecules via chain walking is described. Catalytic cycloisomerization of 1,n-dienes via chain walking was achieved using a palladium-1,10-phenanthroline catalyst to form five-membered-ring products. By means of a cycloisomerization/hydrogenation protocol, 1,7- to 1,14-dienes were selectively converted to bicyclo[4.3.0]nonane derivatives. The use of chain walking provides a new method in organic synthesis to functionalize unreactive carbon-hydrogen bonds by letting the catalyst look for preferable bond-forming sites by moving around on the substrate.

  DOI：

  10.1021/ja308377u

文献信息

• Mn(III)-based oxidative free-radical cyclizations of alkenyl Meldrum's acids
  作者：Barry B. Snider、Rachel B. Smith

  DOI：10.1016/s0040-4020(01)01054-7

  日期：2002.1

  Oxidative cyclization of unsaturated Meldrum's acids can be carried out at temperatures as low as −30°C. The rate-determining step is cyclization of the enolate to the alkene (11 to 14 and 15) rather than enolization, which is the rate-determining step with dimethyl 4-pentenylmalonate (1). While cyclization of 1 gives mainly cyclopentanes, cyclization of Meldrum's acids provides a versatile route to

  不饱和麦德鲁姆酸的氧化环化反应可在低至-30°C的温度下进行。速率确定步骤是烯醇盐环化成烯烃（11至14和15）而不是烯化，这是用4-戊烯基丙二酸二甲酯（1）确定速率的步骤。虽然1的环化主要产生环戊烷，但Meldrum酸的环化提供了通往环己烯的通用途径。
• Organocatalysed decarboxylative protonation process from Meldrum's acid: enantioselective synthesis of isoxazolidinones
  作者：Tony Tite、Mohamad Sabbah、Vincent Levacher、Jean-François Brière

  DOI：10.1039/c3cc47695b

  日期：——

  An asymmetric organocatalysed decarboxylative protonation reaction allowed a straightforward synthesis of α-substituted isoxazolidin-5-ones from readily available 5-substituted Meldrum's acids. This process is initiated by an anionic formal (3+2) cycloaddition–fragmentation, generated in-situ from a sulfone-amide precursor which also served as a latent source of proton.

  一种非对称的有机催化去羧基质子化反应实现了从易得的5-取代梅尔德鲁姆酸中直接合成α-取代的异噁唑烷-5-酮。该过程由一个阴离子形式的（3+2）环加成-裂解反应启动，该反应在原位从一种磺酰胺前体中生成，并且该前体还作为一个潜在的质子来源。
• Conjugate addition of allyltrimethylsilane to electrophilic cyclopropanes
  作者：Ramesh Bambal、Raymond D. W. Kemmitt

  DOI：10.1039/c39880000734

  日期：——

  Allyltrimethylsilane undergoes a Lewis-acid-assisted one-pot conjugate addition with cyclopropanes activated by geminal alkoxycarbonyl groups.

  烯丙基三甲基硅烷经过路易斯酸辅助的一锅共轭加成反应，并被双链烷氧基羰基活化的环丙烷。
• BAMBAL, RAMESH;KEMMITT, RAYMOND D. W., J. CHEM. SOC. CHEM. COMMUN.,(1988) N 11, 734-735
  作者：BAMBAL, RAMESH、KEMMITT, RAYMOND D. W.

  DOI：——

  日期：——