Propanedioic acid, 4-nonynyl-, dimethyl ester | 180691-25-2

• 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: Propanedioic acid, 4-nonynyl-, dimethyl ester
• 英文别名: dimethyl 2-non-4-ynylpropanedioate
• CAS: 180691-25-2
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: AWQNLGKOJKFVTC-UHFFFAOYSA-N

物化性质

• 沸点：
  308.7±32.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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-氯丙烯 、 Propanedioic acid, 4-nonynyl-, dimethyl ester 在 palladium diacetate 苯磺酰胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到
  参考文献：
  名称：

  钯（II）催化的炔烃分子内碳钯反应引发的炔烃与烯丙基化合物的偶联反应

  摘要：

  在二价钯催化下，炔烃与炔烃的环碳烷基缩合引发的烯丙基卤化物的高度区域选择性和立体选择性偶合反应在过量卤化物离子存在下顺利进行。该反应涉及分子内碳氢合反应，将烯丙基化合物插入乙烯基Pd键中以及通过不使用氧化剂的β-杂原子消除一步淬灭CPd键。

  DOI：

  10.1016/s0040-4039(02)01512-5
• 作为产物：
  描述：

  1-氯-4-壬炔 、 丙二酸二甲酯 在 sodium hydride 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 以64%的产率得到Propanedioic acid, 4-nonynyl-, dimethyl ester
  参考文献：
  名称：

  Intramolecular and Intermolecular Mn(III)-Induced Carbon Monoxide Trapping Reactions of Alkynes with Malonate and Cyano Ester Units

  摘要：

  Intra- and intermolecular carbon monoxide trapping reactions of alkynes with malonates and cyano esters were developed using a Mn(III)-induced oxidative system. Phenylacetylene was treated with diethyl ethylmalonate in the presence of Mn(OAc)(3) . 2H(2)O, in AcOH-CH3CN (1:1) under carbon monoxide, affording (Z)-4,4-dicarbethoxy-2-phenyl-2-hexenoic acid. Similarly, intramolecular reactions of 4-alkynylmalonates and cyanoacetates proceeded regio- and stereoselectively under the same conditions to afford the corresponding methylenecycloalkanecarboxylic acids in moderate yields. The reaction involves carbon monoxide trapping of vinyl radicals which are formed by the addition of malonate or cyanoacetate radicals induced by Mn(III) to alkynes.

  DOI：

  10.1021/jo9607673

文献信息

• Intramolecular and Intermolecular Mn(III)-Induced Carbon Monoxide Trapping Reactions of Alkynes with Malonate and Cyano Ester Units
  作者：Kazumi Okuro、Howard Alper

  DOI：10.1021/jo9607673

  日期：1996.1.1

  Intra- and intermolecular carbon monoxide trapping reactions of alkynes with malonates and cyano esters were developed using a Mn(III)-induced oxidative system. Phenylacetylene was treated with diethyl ethylmalonate in the presence of Mn(OAc)(3) . 2H(2)O, in AcOH-CH3CN (1:1) under carbon monoxide, affording (Z)-4,4-dicarbethoxy-2-phenyl-2-hexenoic acid. Similarly, intramolecular reactions of 4-alkynylmalonates and cyanoacetates proceeded regio- and stereoselectively under the same conditions to afford the corresponding methylenecycloalkanecarboxylic acids in moderate yields. The reaction involves carbon monoxide trapping of vinyl radicals which are formed by the addition of malonate or cyanoacetate radicals induced by Mn(III) to alkynes.
• Palladium(II)-catalyzed coupling reactions of alkynes and allylic compounds initiated by intramolecular carbopalladation of alkynes
  作者：Guosheng Liu、Xiyan Lu

  DOI：10.1016/s0040-4039(02)01512-5

  日期：2002.9

  Under divalent palladium catalysis, a highly regio- and stereoselective coupling reaction of alkynes with allyl halides initiated by cyclocarbopalladation of alkynes proceeded smoothly in the presence of excess halide ions. The reaction involves intramolecular carbopalladation, allylic compound insertion into the vinylicPd bond and quenching the CPd bond by β-heteroatom elimination in one step without

  在二价钯催化下，炔烃与炔烃的环碳烷基缩合引发的烯丙基卤化物的高度区域选择性和立体选择性偶合反应在过量卤化物离子存在下顺利进行。该反应涉及分子内碳氢合反应，将烯丙基化合物插入乙烯基Pd键中以及通过不使用氧化剂的β-杂原子消除一步淬灭CPd键。