5-chloro-2-(3-methoxyprop-1-yn-1-yl)benzaldehyde | 1298062-89-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-chloro-2-(3-methoxyprop-1-yn-1-yl)benzaldehyde
• CAS: 1298062-89-1
• 化学式: C₁₁H₉ClO₂
• 分子量: 208.644
• InChiKey: OXLRLAFQSKSELB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(3-methoxyprop-1-yn-1-yl)benzaldehyde 在 1,10-菲罗啉 、 palladium diacetate 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 37.0h， 生成 [5-chloro-2-(methoxymethyl)-3-(2-oxopropyl)-3H-inden-1-yl] acetate
  参考文献：
  名称：

  Palladium(II)-Catalyzed Synthesis of Functionalized Indenes from o-Alkynylbenzylidene Ketones

  摘要：

  An efficient method for the synthesis of functionalized indenes from o-alkynylbenzylidene ketones under palladium(II) catalysis was developed. The reaction is initiated by trans-nucleopalladation of alkynes, followed by conjugate addition and quenched by protonolysis of the carbon palladium bond. With acetate and halide ions as nucleophiles, 3-acetoxy- and 3-halogen-substituted indenes could be obtained in high yields.

  DOI：

  10.1021/jo1023574
• 作为产物：
  描述：

  2-溴-5-氯苯甲醛 、 甲基炔丙基醚 在 copper(l) iodide 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以73%的产率得到5-chloro-2-(3-methoxyprop-1-yn-1-yl)benzaldehyde
  参考文献：
  名称：

  Palladium(II)-Catalyzed Synthesis of Functionalized Indenes from o-Alkynylbenzylidene Ketones

  摘要：

  An efficient method for the synthesis of functionalized indenes from o-alkynylbenzylidene ketones under palladium(II) catalysis was developed. The reaction is initiated by trans-nucleopalladation of alkynes, followed by conjugate addition and quenched by protonolysis of the carbon palladium bond. With acetate and halide ions as nucleophiles, 3-acetoxy- and 3-halogen-substituted indenes could be obtained in high yields.

  DOI：

  10.1021/jo1023574

文献信息

• An Unexpected Addition of Acetic Acid to<i>ortho</i>-Electron- Deficient Alkynyl-Substituted Aryl Aldehydes Catalyzed by Palladium(II) Acetate
  作者：Jianbo Zhang、Xiuling Han

  DOI：10.1002/adsc.201301170

  日期：2014.8.11

  AbstractAn unexpected addition of acetic acid to ortho‐electron‐deficient alkynyl‐substituted aryl aldehydes catalyzed by palladium(II) acetate was achieved, which provided a convenient method for the synthesis of dihydroisobenzofurans in moderate to good yields. The electron‐withdrawing groups attached to alkynes may play an important role for the cyclization.magnified image