2-(6,7-dimethoxyisoquinolin-1-yl)-5-methoxybenzonitrile | 83287-05-2

• 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: 2-(6,7-dimethoxyisoquinolin-1-yl)-5-methoxybenzonitrile
• 英文别名: 2-(6,7-Dimethoxyisoquinolin-1-yl)-5-methoxybenzonitrile
• CAS: 83287-05-2
• 化学式: C₁₉H₁₆N₂O₃
• 分子量: 320.348
• InChiKey: ZMMMDUKGWXPHEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(6,7-dimethoxyisoquinolin-1-yl)-5-methoxybenzonitrile 在 氢氧化钾 、 水 作用下， 以 甲醇 、 乙醚 、 二乙二醇 为溶剂， 反应 24.0h， 生成 methyl 2-(6,7-dimethoxyisoquinolin-1-yl)-5-methoxybenzoate
  参考文献：
  名称：

  Structure and synthesis of menisporphine, a new type of isoquinoline alkaloid

  摘要：

  DOI：

  10.1016/s0040-4020(01)91573-x
• 作为产物：
  描述：

  4-甲氧基苯甲酰胺 在 2-氯吡啶 、 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 三氟甲磺酸酐 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 38.0h， 生成 2-(6,7-dimethoxyisoquinolin-1-yl)-5-methoxybenzonitrile
  参考文献：
  名称：

  Rhodium Catalyzed Cyanation of Chelation Assisted C–H Bonds

  摘要：

  A rhodium-catalyzed cyanation of chelation assisted C-H bonds is described employing N-cyano-N-phenyl-p-methylbenzenesulfonamide as an efficient cyanating reagent. The present method allowed the synthesis of various benzonitirle derivatives in good to excellent yield. A number of chelating groups are also effective in the present cyanation of C-H bonds. In addition, the developed methodology was applied in the formal synthesis of the isoquinoline alkaloid, menisporphine.

  DOI：

  10.1021/ol402201c

文献信息

• Chelation-Assisted Palladium-Catalyzed Direct Cyanation of 2-Arylpyridine C−H Bonds
  作者：Xiaofei Jia、Dongpeng Yang、Shouhui Zhang、Jiang Cheng

  DOI：10.1021/ol9017529

  日期：2009.10.15

  A chelation-assisted palladium-catalyzed ortho-cyanation of the sp2 C−H bond by CuCN provided aromatic nitriles in moderate to good yields. Notably, the reaction could be conducted on a 10 mmol scale. The key intermediate of the natural product of Menispermum dauricum DC was concisely synthesized by the procedure. This new approach represents an exceedingly practical method for the synthesis of aromatic

  CuCN的螯合辅助钯催化的sp 2 C-H键的正氰基化提供了中等至良好的收率的芳族腈。值得注意的是，该反应可以以10mmol规模进行。该方法简明扼要地合成了半月板DC天然产物的关键中间体。这种新方法代表了一种合成芳族腈的极为实用的方法，并为传统的桑德迈尔反应提供了有吸引力的替代方法。
• Ni-Catalyzed C–H Cyanation of (Hetero)arenes with 2-Cyanoisothiazolidine 1,1-Dioxide as a Cyanation Reagent
  作者：Junjie Ma、Hao Liu、Xin He、Zhicheng Chen、Yue Liu、Chuanfu Hou、Zhizhong Sun、Wenyi Chu

  DOI：10.1021/acs.orglett.1c00468

  日期：2021.4.16

  A nickel-catalyzed C–H cyanation reaction of arenes has been developed using 2-cyanoisothiazolidine 1,1-dioxide as an electrophilic cyanation reagent. Many different directing groups can be used in this cyanation to obtain a series of cyanation products with good yields. Adopting this strategy to introduce a cyano group, natural alkaloid menisporphine was successfully synthesized through cyano group

  使用2-氰基异噻唑烷1，1-二氧化物作为亲电子氰化试剂已开发出镍催化的芳烃的CH氰化氰化反应。在该氰化反应中可以使用许多不同的导向基团，以获得具有良好收率的一系列氰化反应产物。采用这种引入氰基的策略，通过氰基的转化成功合成了天然生物碱半胱氨酸，进一步证明了该氰化方法的实用性。
• Structure of menisporphine: A new type of isoquinoline alkaloid.
  作者：Junichi Kunitomo、Miyoko Satoh

  DOI：10.1248/cpb.30.2659

  日期：——

  The structure of an unknown yellow base from Menisperum dauricum DC. (Menispermaceae) was determined to be 5, 6, 9-trimethoxy-7H-dibenzo [de, h] quinolin-7-one (1) by spectral data and total synthesis. It was named menisporphine and the skeletal name"oxoisoaporphine"was proposed for this new type of alkaloid. The biosynthesis route of oxoisoaporphine-type alkaloids in plants is suggested.

  通过光谱数据和全合成，确定了来自 Menisperum dauricum DC.(Menispermaceae) 中的一种未知黄色碱的结构，通过光谱数据和全合成确定为 5, 6, 9-三甲氧基-7H-二苯并 [de, h] 喹啉-7-酮（1）。它被命名为 menisporphine，并为这种新型生物碱提出了 "oxoisoaporphine "这一骨架名称。提出了氧化异阿扑啡类生物碱在植物中的生物合成途径。
• Rhodium Catalyzed Cyanation of Chelation Assisted C–H Bonds
  作者：Manthena Chaitanya、Dongari Yadagiri、Pazhamalai Anbarasan

  DOI：10.1021/ol402201c

  日期：2013.10.4

  A rhodium-catalyzed cyanation of chelation assisted C-H bonds is described employing N-cyano-N-phenyl-p-methylbenzenesulfonamide as an efficient cyanating reagent. The present method allowed the synthesis of various benzonitirle derivatives in good to excellent yield. A number of chelating groups are also effective in the present cyanation of C-H bonds. In addition, the developed methodology was applied in the formal synthesis of the isoquinoline alkaloid, menisporphine.
• Structure and synthesis of menisporphine, a new type of isoquinoline alkaloid
  作者：J. Kunitomo、M. Satoh、T. Shingu

  DOI：10.1016/s0040-4020(01)91573-x

  日期：1983.1