1-methoxy-3-phenylisoquinoline

• 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-methoxy-3-phenylisoquinoline
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: ZHOUBMHKZHMULO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methoxy-3-phenylisoquinoline 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以97%的产率得到3-phenyl-2H-isoquinolin-1-one
  参考文献：
  名称：

  Platinum(II)-catalyzed intramolecular cyclization of alkynylbenzonitriles: synthesis of 1-alkoxyisoquinolines and isoquinolones

  摘要：

  A facile synthesis of a series of 1-alkoxyisoguinolines and (2H)-isoguinolones by an intramolecular 6-endo-dig cyclization of ortho-alkynylbenzonitriles in the presence of a catalytic amount of hydrido(dimethylphosphinous acid-kappa P)[hydrogen bis(dimethylphosphinito-kappa P)]platinum(II) in various alcohols at 65-90 degrees C is described for the first time. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.136
• 作为产物：
  描述：

  苯甲腈 在 3,5-二甲基苯甲酸 、 [RhCl2(p-cymene)]2 、 乙酰氯 作用下， 以 乙醇 、 2,2,2-三氟乙醇 为溶剂， 反应 18.0h， 生成 1-methoxy-3-phenylisoquinoline
  参考文献：
  名称：

  钌（II）催化的苯甲酸酯和磺酸亚砜盐类的无氧化剂偶联/环化反应生成取代的异喹啉

  摘要：

  已经开发出了苯甲酸酯和亚砜基鎓盐的钌催化直接单CH功能化/环化级联反应。反应可在多种底物上顺利进行，使用有机酸添加剂在无氧化剂的条件下，可以以中等到良好的产率获得各种异喹啉衍生物。

  DOI：

  10.1002/adsc.201800844

文献信息

• [EN] HEPATITIS C INHIBITOR PEPTIDE ANALOGS<br/>[FR] ANALOGUES PEPTIDIQUES D'INHIBITEURS DE L'HEPATITE C
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2006000085A1

  公开（公告）日：2006-01-05

  The invention relates to compounds of formula (I) wherein R', R2, R3, R4, R5, R6, Y, n and m are as defined herein. The compounds are useful for the treatment and prevention of hepatitis C viral infections in mammals by inhibiting HCV NS3 protease. The invention further relates to azalactone compounds of the formula (III) which can be reacted with an amide anion to produce the compounds of formula (I).

  本发明涉及式(I)的化合物，其中R'，R2，R3，R4，R5，R6，Y，n和m如本文所述定义。这些化合物通过抑制HCV NS3蛋白酶，用于治疗和预防哺乳动物中的丙型肝炎病毒感染。本发明进一步涉及可以与酰胺阴离子反应以产生式(I)化合物的azalactone化合物（III）。
• Highly stereoselective synthesis of (Z)-3-methoxy-1-methyleneisoindoles via DMAP catalyzed cyclization of methyl 2-alkynylbenzimidates
  作者：Tuanli Yao、Xiujuan Liang、Zhen Guo、Dong Yang

  DOI：10.1016/j.tet.2019.04.036

  日期：2019.6

  A DMAP (4-dimethylaminopyridine) catalyzed cyclization of methyl 2-alkynylbenzimidates has been developed, which affords 3-methoxy-1-methyleneisoindoles with excellent Z-stereoselectivity under mild and transition-metal-free conditions. The (Z)-3-methoxy-1-methyleneisoindole products can be converted to corresponding 3-amino-1-methyleneisoindoles, 3-methoxy-isoindoles, 3-methyleneisoindolinones and

  已经开发了一种DMAP（4-二甲基氨基吡啶）催化2-炔基苯并咪唑酸甲酯的环化反应，该化合物在温和且无过渡金属的条件下提供具有出色的Z-立体选择性的3-甲氧基-1-亚甲基异吲哚。（Z）-3-甲氧基-1-亚甲基异吲哚产物可以高效地转化为相应的3-氨基-1-亚甲基异吲哚，3-甲氧基-异吲哚，3-亚甲基异吲哚满酮和异吲哚满酮。
• Regio- and Stereoselective Electrophilic Cyclization Approach for the Protecting-Group-Free Synthesis of Alkaloids Lennoxamine, Chilenine, Fumaridine, 8-Oxypseudoplamatine, and 2-<i>O</i>-(Methyloxy)fagaronine
  作者：Tuanli Yao、Zhen Guo、Xiujuan Liang、Lihan Qi

  DOI：10.1021/acs.joc.8b02154

  日期：2018.11.2

  protecting-group-free synthesis of alkaloids lennoxamine, chilenine, fumaridine, 8-oxypseudoplamatine, and 2-O-(methyloxy)fagaronine is reported. The core isoindolin-1-one and isoquinolin-1-one structures were built by a silver-catalyzed regio- and stereoselective cyclization of methyl 2-alkynylbenzimidates. The regioselectivity of cyclization was achieved by utilizing the intrinsic functionality of alkaloids.

  报导了一种统一的策略，用于生物碱伦诺沙明，苯胺，富马立定，8-氧代伪pla胺和2- O-（甲氧基）法加宁的无保护基合成。核心异吲哚啉-1-酮和异喹啉-1-酮结构是通过银催化的2-炔基苯并咪唑酸甲酯的区域和立体选择性环化而建立的。环化的区域选择性是通过利用生物碱的内在功能实现的。
• Synthesis of isoquinolines by irradiation of 1-methoxy-2-azabuta-1,3-dienes in a neutral medium
  作者：Pedro J Campos、Mı́riam Caro、Miguel A Rodrı́guez

  DOI：10.1016/s0040-4039(01)00498-1

  日期：2001.5

  We describe, for the first time, the photocyclization of 2-azadienes in a neutral medium. The reaction leads to the formation of isoquinolines. (C) 2001 Elsevier Science Ltd, All rights reserved.
• Role of the electron-donating methoxy group on the photo-induced cyclization of 2-azadienes: a mechanistic study
  作者：Pedro J. Campos、Míriam Caro、Miguel A. Rodríguez

  DOI：10.1016/j.tet.2013.07.015

  日期：2013.9

  A combined experimental and computational investigation has shown that the photocyclization of 2-azadienes to isoquinolines is consistent with a unimolecular process in the triplet state and that the (n,pi*) transition is involved. The presence of a methoxy group favours the photoreaction. According to calculations, the reaction should proceed by a conformational equilibrium in the ground state followed by excitation and subsequent cyclization. The presence of an equilibrated triplet-state intermediate along the reaction path is consistent with a measurable luminescence. (C) 2013 Elsevier Ltd. All rights reserved.