ethyl 2-acetyl-4-methyl-5-phenylmethyl-5-hexenoate | 1225287-58-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 2-acetyl-4-methyl-5-phenylmethyl-5-hexenoate
• 英文别名: Ethyl 2-acetyl-5-benzyl-4-methylhex-5-enoate
• CAS: 1225287-58-0
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: VKRAGVQRGQRUIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Ethyl 1-acetyl-3-methyl-4-methylidenecyclopentane-1-carboxylate 、 benzene,bromozinc(1+) 在 dibromobis(triphenylphosphine)nickel(II) 、 magnesium bromide 、 氯化铵 作用下， 以 四氢呋喃 、 甲苯 、 水 为溶剂， 反应 8.0h， 以78%的产率得到ethyl 2-acetyl-4-methyl-5-phenylmethyl-5-hexenoate
  参考文献：
  名称：

  Nickel-Catalyzed Arylative Ring-Opening of 3-Methylenecycloalkane-1,1-dicarboxylates

  摘要：

  An arylative ring-opening reaction of cyclic allylmalonates with arylzinc reagents under nickel catalysis has been developed. Upon the ring-opening sp(3)C-sp(3)C bond cleavage, the allylic moiety serves as an allylic electrophile to react with arylzinc reagents. Simultaneously, the malonate moiety is converted to the corresponding zinc enolate, which can react further with electrophiles. The overall process increases molecular complexity and diversity starting from readily available substrates and is useful in organic synthesis.

  DOI：

  10.1021/ol100599c

文献信息

• Nickel-Catalyzed Arylative Ring-Opening of 3-Methylenecycloalkane-1,1-dicarboxylates
  作者：Yuto Sumida、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1021/ol100599c

  日期：2010.5.21

  An arylative ring-opening reaction of cyclic allylmalonates with arylzinc reagents under nickel catalysis has been developed. Upon the ring-opening sp(3)C-sp(3)C bond cleavage, the allylic moiety serves as an allylic electrophile to react with arylzinc reagents. Simultaneously, the malonate moiety is converted to the corresponding zinc enolate, which can react further with electrophiles. The overall process increases molecular complexity and diversity starting from readily available substrates and is useful in organic synthesis.