1-phenyl-3,4-dipropylisoquinoline 2-oxide | 1352638-45-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-phenyl-3,4-dipropylisoquinoline 2-oxide
• 英文别名: 2-Oxido-1-phenyl-3,4-dipropylisoquinolin-2-ium；2-oxido-1-phenyl-3,4-dipropylisoquinolin-2-ium
• CAS: 1352638-45-9
• 化学式: C₂₁H₂₃NO
• 分子量: 305.42
• InChiKey: JYWLXSTWZSHIJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  25.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-辛炔 、 二苯甲酮肟 在 palladium diacetate 、 三氟乙酸 、 zinc dibromide 作用下， 以 1,4-二氧六环 、 氯苯 为溶剂， 反应 5.0h， 以59%的产率得到1-phenyl-3,4-dipropylisoquinoline 2-oxide
  参考文献：
  名称：

  Isoquinoline N-Oxide Synthesis under Pd-Catalysed C-H Activation/Annulation Processes

  摘要：

  An oxime directed C-H activation-annulation reaction for the selective synthesis of a range of isoquinoline N-oxides has been developed. Under palladium-catalyzed acid-assisted conditions, the reaction undergoes concerted metallation deprotonation followed by carbopalladation and transmetallation to give polysubstituted isoquinoline N-oxides in moderate to good yields.

  DOI：

  10.1055/s-0033-1339671

文献信息

• Nickel-catalyzed Cycloaddition of Aromatic (<i>O</i>-Benzyl)ketoximes with Alkynes to Produce Isoquinoline and Isoquinoline<i>N</i>-Oxide Derivatives
  作者：Yuji Yoshida、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1246/cl.2011.1140

  日期：2011.10.5

  A nickel-catalyzed cycloaddition of aromatic (O-benzyl)ketoximes with alkynes to afford 3,4-disubstituted isoquinoline derivatives has been developed. The reaction involves oxidative addition of N–O bond of O-benzylketoxime to Ni(0) and subsequent intermolecular C–H bond activation via elimination of benzyl alcohol. It was also found that ketoximes participate in the nickel-catalyzed reaction with alkynes to furnish isoquinoline N-oxide derivatives.

  研究人员开发了一种镍催化的芳香族（O-苄基）酮肟与炔烃的环加成反应，从而制备出 3,4-二取代的异喹啉衍生物。该反应涉及 O-苄基酮肟的 N-O 键与 Ni(0) 的氧化加成，以及随后通过消除苄醇激活分子间的 C-H 键。研究还发现，酮肟参与了镍催化的炔烃反应，生成异喹啉 N-氧化物衍生物。
• Isoquinoline N-Oxide Synthesis under Pd-Catalysed C-H Activation/Annulation Processes
  作者：Jianhui Huang、Bingyao Li、Pingxuan Jiao、Hongban Zhong

  DOI：10.1055/s-0033-1339671

  日期：——

  An oxime directed C-H activation-annulation reaction for the selective synthesis of a range of isoquinoline N-oxides has been developed. Under palladium-catalyzed acid-assisted conditions, the reaction undergoes concerted metallation deprotonation followed by carbopalladation and transmetallation to give polysubstituted isoquinoline N-oxides in moderate to good yields.