isopropyl 4-methoxy-2-butynoate | 491595-78-9

• 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: isopropyl 4-methoxy-2-butynoate
• 英文别名: Propan-2-yl 4-methoxybut-2-ynoate
• CAS: 491595-78-9
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: FWWLDURZQYKLOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isopropyl 4-methoxy-2-butynoate 在 盐酸 、 palladium diacetate 、 三正丁胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 24.0h， 生成 阿贝卡尔
  参考文献：
  名称：

  Synthesis of β- and γ-Carbolines by the Palladium-Catalyzed Iminoannulation of Alkynes

  摘要：

  A variety of substituted beta- and gamma-carbolines have been prepared in moderate to excellent yields by the palladium-catalyzed annulation of internal and terminal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively. This annulation chemistry is effective for a wide range of alkynes, including aryl-, alkyl-, hydroxymethyl-, ethoxycarbonyl-, and trimethylsilyl-substituted alkynes. When an unsymmetrical internal alkyne is employed, this method generally gives two regioisomers. When a terminal alkyne is employed, only one regioisomer has been isolated. This palladium-catalyzed annulation chemistry has also been successfully applied to the synthesis of two biologically interesting beta-carboline alkaloids, ZK93423 and abecarnil (ZK112119).

  DOI：

  10.1021/jo026317u
• 作为产物：
  描述：

  氯甲酸异丙酯 、 甲基炔丙基醚 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以52%的产率得到isopropyl 4-methoxy-2-butynoate
  参考文献：
  名称：

  Synthesis of β- and γ-Carbolines by the Palladium-Catalyzed Iminoannulation of Alkynes

  摘要：

  A variety of substituted beta- and gamma-carbolines have been prepared in moderate to excellent yields by the palladium-catalyzed annulation of internal and terminal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively. This annulation chemistry is effective for a wide range of alkynes, including aryl-, alkyl-, hydroxymethyl-, ethoxycarbonyl-, and trimethylsilyl-substituted alkynes. When an unsymmetrical internal alkyne is employed, this method generally gives two regioisomers. When a terminal alkyne is employed, only one regioisomer has been isolated. This palladium-catalyzed annulation chemistry has also been successfully applied to the synthesis of two biologically interesting beta-carboline alkaloids, ZK93423 and abecarnil (ZK112119).

  DOI：

  10.1021/jo026317u

文献信息

• Synthesis of β- and γ-Carbolines by the Palladium-Catalyzed Iminoannulation of Alkynes
  作者：Haiming Zhang、Richard C. Larock

  DOI：10.1021/jo026317u

  日期：2002.12.1

  A variety of substituted beta- and gamma-carbolines have been prepared in moderate to excellent yields by the palladium-catalyzed annulation of internal and terminal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively. This annulation chemistry is effective for a wide range of alkynes, including aryl-, alkyl-, hydroxymethyl-, ethoxycarbonyl-, and trimethylsilyl-substituted alkynes. When an unsymmetrical internal alkyne is employed, this method generally gives two regioisomers. When a terminal alkyne is employed, only one regioisomer has been isolated. This palladium-catalyzed annulation chemistry has also been successfully applied to the synthesis of two biologically interesting beta-carboline alkaloids, ZK93423 and abecarnil (ZK112119).