ethyl 5-(o-chloromethyl)phenyl-2-ethoxycarbonyl-4-methylenepentanoate | 136911-10-9

• 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: ethyl 5-(o-chloromethyl)phenyl-2-ethoxycarbonyl-4-methylenepentanoate
• 英文别名: diethyl 2-[2-[[2-(chloromethyl)phenyl]methyl]prop-2-enyl]propanedioate
• CAS: 136911-10-9
• 化学式: C₁₈H₂₃ClO₄
• 分子量: 338.831
• InChiKey: MHBFVLKVZAMCEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  一氧化碳 、 ethyl 5-(o-chloromethyl)phenyl-2-ethoxycarbonyl-4-methylenepentanoate 在 bis-triphenylphosphine-palladium(II) chloride 三乙胺 作用下， 以 乙腈 为溶剂， 100.0 ℃ 、4.14 MPa 条件下， 以47 (unit not given)的产率得到2-(2-Oxo-2,3-dihydro-4H-naphtho[2,3-b]furan-3a-ylmethyl)-malonic acid diethyl ester
  参考文献：
  名称：

  Palladium-catalyzed carbonylative cyclization of o-allylbenzyl halides to produce benzo-annulated enol lactones and/or bicyclo[3.3.0]hept-3-en-6-ones. An efficient route to U-68,215

  摘要：

  Treatment of omicron-allylbenzyl halides with CO in the presence of 1.5-2.0 equiv of a base, such as NEt3, and a catalytic amount of a palladium complex, such as Cl2Pd(PPh3)2, provides a 2,3,3a,4-tetrahydro-2-oxonaphthyl[2,3-b]furans and/or cyclovutanone derivatives tentatively identified as 2,2a,7,7a-tetrahydro-1H-cyclobut[a]inden-2-ones.

  DOI：

  10.1021/jo00023a011

文献信息

• Palladium-catalyzed carbonylative cyclization via trapping of acylpalladium derivatives with internal enolates. Its scope and factors affecting the C-to-O ratio
  作者：El-ichi Negishi、Christophe Copéret、Takumichi Sugihara、Izumi Shimoyama、Yantao Zhang、Guangzhong Wu、James M. Tour

  DOI：10.1016/s0040-4020(01)80765-1

  日期：1994.1

  The Pd-catalyzed carbonylative cyclization reaction involving omega-acyl-substituted acylpalladium derivatives can proceed via intramolecular trapping with either C- or O-enolates; the preferential formation of either 5- or 6-membered rings dictates the C-to-O ratio in the trapping with enolates.