Diethyl 2-[(5-ethylpyridin-2-yl)methyl]propanedioate | 134208-95-0

• 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: Diethyl 2-[(5-ethylpyridin-2-yl)methyl]propanedioate
• CAS: 134208-95-0
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: UIKFCQGHTQFUJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  辛烯 、 Diethyl 2-[(5-ethylpyridin-2-yl)methyl]propanedioate 在 manganese triacetate 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 以89%的产率得到3-ethyl-5-hexyl-7,7-bis(ethoxycarbonyl)-5,6,7,8-tetrahydroquinoline
  参考文献：
  名称：

  Oxidation of diethyl (pyridylmethyl)malonates with manganese(III) acetate, cerium(IV) ammonium nitrate, and iron(III) perchlorate in the presence of alkenes and alkynes

  摘要：

  The oxidation of substituted diethyl 2-, 3-, or 4-picolylmalonates (1a-g) by Mn(III) acetate in acetic acid, Ce(IV) ammonium nitrate in methanol or acetic acid, and Fe(III) perchlorate in acetonitrile in the presence of substituted alkenes (2) and alkynes (3) affords substituted tetra- or dihydroquinolines and/or isoquinolines (4-9) in good to excellent yield. The influence of reaction medium on yield and isomer distribution has been investigated. A mechanism involving oxidative deprotonation of malonic esters by high-valent metal salts to malonyl radicals, their addition to olefins, and intramolecular homolytic substitution to protonated or metal-complexed heteroaromatic bases by the resulting substituted carbon radicals is suggested.

  DOI：

  10.1021/jo00018a024
• 作为产物：
  描述：

  丙二酸二乙酯钠盐 、 2-chloromethyl-5-ethyl-pyridine-hydrochloride 以 四氢呋喃 为溶剂， 生成 Diethyl 2-[(5-ethylpyridin-2-yl)methyl]propanedioate
  参考文献：
  名称：

  Oxidation of diethyl (pyridylmethyl)malonates with manganese(III) acetate, cerium(IV) ammonium nitrate, and iron(III) perchlorate in the presence of alkenes and alkynes

  摘要：

  The oxidation of substituted diethyl 2-, 3-, or 4-picolylmalonates (1a-g) by Mn(III) acetate in acetic acid, Ce(IV) ammonium nitrate in methanol or acetic acid, and Fe(III) perchlorate in acetonitrile in the presence of substituted alkenes (2) and alkynes (3) affords substituted tetra- or dihydroquinolines and/or isoquinolines (4-9) in good to excellent yield. The influence of reaction medium on yield and isomer distribution has been investigated. A mechanism involving oxidative deprotonation of malonic esters by high-valent metal salts to malonyl radicals, their addition to olefins, and intramolecular homolytic substitution to protonated or metal-complexed heteroaromatic bases by the resulting substituted carbon radicals is suggested.

  DOI：

  10.1021/jo00018a024

文献信息

• CITTERIO, ATTILIO;SEBASTIANO, ROBERTO;CARVAYAL, MAGALY CACERES, J. ORG. CHEM., 56,(1991) N8, C. 5335-5341
  作者：CITTERIO, ATTILIO、SEBASTIANO, ROBERTO、CARVAYAL, MAGALY CACERES

  DOI：——

  日期：——
• Oxidation of diethyl (pyridylmethyl)malonates with manganese(III) acetate, cerium(IV) ammonium nitrate, and iron(III) perchlorate in the presence of alkenes and alkynes
  作者：Attilio Citterio、Roberto Sebastiano、Magaly Caceres Carvayal

  DOI：10.1021/jo00018a024

  日期：1991.8

  The oxidation of substituted diethyl 2-, 3-, or 4-picolylmalonates (1a-g) by Mn(III) acetate in acetic acid, Ce(IV) ammonium nitrate in methanol or acetic acid, and Fe(III) perchlorate in acetonitrile in the presence of substituted alkenes (2) and alkynes (3) affords substituted tetra- or dihydroquinolines and/or isoquinolines (4-9) in good to excellent yield. The influence of reaction medium on yield and isomer distribution has been investigated. A mechanism involving oxidative deprotonation of malonic esters by high-valent metal salts to malonyl radicals, their addition to olefins, and intramolecular homolytic substitution to protonated or metal-complexed heteroaromatic bases by the resulting substituted carbon radicals is suggested.