1-butyl-3,4-diphenylisoquinoline | 1359715-95-9

• 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-butyl-3,4-diphenylisoquinoline
• 英文别名: 1-Butyl-3,4-diphenylisoquinoline
• CAS: 1359715-95-9
• 化学式: C₂₅H₂₃N
• 分子量: 337.464
• InChiKey: PIYWCSUEIJUHKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲基苯戊酮 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 12.0h， 生成 1-butyl-3,4-diphenylisoquinoline
  参考文献：
  名称：

  Synthesis of Isoquinolines via Rh(III)-Catalyzed C–H Activation Using Hydrazone as a New Oxidizing Directing Group

  摘要：

  An efficient and mechanistically interesting method for the synthesis of highly substituted isoquinolines by a Rh(III)-catalyzed hydrazone directed ortho C H bond activation and annulation without an external oxidant is described. This reaction is accomplished via a C-C and C-N bond formation along with N-N bond cleavage.

  DOI：

  10.1021/ol402796m

文献信息

• Ruthenaelectro‐Catalyzed Domino Three‐Component Alkyne Annulation for Expedient Isoquinoline Assembly
  作者：Xuefeng Tan、Xiaoyan Hou、Torben Rogge、Lutz Ackermann

  DOI：10.1002/anie.202014289

  日期：2021.2.23

  The electrochemical three‐component assembly of isoquinolines has been accomplished by ruthenaelectro‐catalyzed C−H/N−H functionalization. The robustness of the electrocatalysis was reflected by an ample substrate scope, an efficient electrooxidation, and an operationally friendly procedure. The isolation of key intermediates and detailed mechanistic studies, including unprecedented cyclovoltammetric

  异喹啉的电化学三组分组装已通过钌电子催化的CH / NH官能团完成。电催化的坚固性通过足够的底物范围，有效的电氧化作用和操作友好的程序得以体现。关键中间体的分离和详细的机理研究，包括对七元钌循环的前所未有的循环伏安分析，为不寻常的钌（II / III / I）机制提供了支持。
• (Pentamethylcyclopentadienyl)cobalt(III)-Catalyzed Oxidative [4+2] Annulation of NH Imines with Alkynes: Straightforward Synthesis of Multisubstituted Isoquinolines
  作者：Shang-Shi Zhang、Xu-Ge Liu、Shi-Yong Chen、Dong-Hang Tan、Chun-Yong Jiang、Jia-Qiang Wu、Qingjiang Li、Honggen Wang

  DOI：10.1002/adsc.201600025

  日期：2016.5.19

  A synthetic method for isoquinoline synthesis via a [4+2] annulation of NH imines with alkynes using the high‐valent (pentamethylcyclopentadienyl)cobalt(III) [Cp*Co(III)] catalyst is described. Cerium(IV) sulfate was found to be an efficient oxidant in lieu of the commonly used copper or silver salts. Broad substrate scope, high functional group tolerance, and generally good yields were observed.

  为异喹啉合成的合成方法通过[4 + 2] N中的环 ħ亚胺与使用高价的（五甲基环戊二烯）合钴（III）炔烃的[Cp *钴（III）]的催化剂进行说明。发现硫酸铈（IV）代替常用的铜盐或银盐是有效的氧化剂。观察到广泛的底物范围，高官能团耐受性和通常良好的产率。
• Nickel-Catalyzed Cyclization of ortho-Iodoketoximes and ortho-Iodoketimines with Alkynes: Synthesis of Highly Substituted Isoquinolines and Isoquinolinium Salts
  作者：Wei-Chun Shih、Chu-Chun Teng、Kanniyappan Parthasarathy、Chien-Hong Cheng

  DOI：10.1002/asia.201100834

  日期：2012.2.6

  A convenient method for the synthesis of highly substituted isoquinolines and isoquinolinium salts by the nickel‐catalyzed cyclization of ortho‐haloketoximes and ‐ketimines, respectively, with alkynes is described. The reaction of ortho‐haloketoximes and various alkynes in the presence of [Ni(PPh3)2Br2] and zinc powder in a mixture of acetonitrile and tetrahydrofuran at 80 °C for 15 hours gave 1,3

  描述了一种方便的方法，该方法通过炔烃分别通过邻位卤代酮肟和酮缩酮的镍催化环化反应来合成高度取代的异喹啉和异喹啉鎓盐。在[Ni（PPh 3）2 Br 2 ]和锌粉在乙腈和四氢呋喃的混合物中，邻卤代酮肟和各种炔烃在80°C下反应15小时，得到1,3,4-三取代异喹啉产物具有中等至优异的产量和较高的区域选择性。发现相应的异喹啉N-氧化物是环化反应途径中的中间体。相反，邻位反应卤代亚胺和炔烃在相似的催化条件下，在四氢呋喃中于70°C加热2小时，可得到1,2,3,4-四取代的异喹啉鎓盐，收率很好。
• Manganese-Catalyzed Dehydrogenative [4+2] Annulation of NH Imines and Alkynes by CH/NH Activation
  作者：Ruoyu He、Zhi-Tang Huang、Qi-Yu Zheng、Congyang Wang

  DOI：10.1002/anie.201402575

  日期：2014.5.5

  Described herein is a manganese‐catalyzed dehydrogenative [4+2] annulation of NH imines and alkynes, a reaction providing highly atom‐economical access to diverse isoquinolines. This transformation represents the first example of manganese‐catalyzed CH activation of imines; the stoichiometric variant of the cyclomanganation was reported in 1971. The redox neutral reaction produces H2 as the major

  本文中描述为N的锰催化脱氢[4 + 2]环 ħ亚胺和炔烃的反应提供高度原子经济获取各种异喹啉。这种转变代表了锰催化亚胺的CH活化的第一个例子。1971年报道了环锰的化学计量变体。氧化还原中性反应产生H 2作为主要副产物，消除了对任何氧化剂，外部配体或添加剂的需要，因此在过渡金属催化的C的已知异喹啉合成中脱颖而出。H激活。机理研究表明，五元锰环和氢化锰是催化循环中的关键反应中间体。
• Redox-Divergent Hydrogen-Retentive or Hydrogen-Releasing Synthesis of 3,4-Dihydroisoquinolines or Isoquinolines
  作者：Ke-Han He、Wei-Dong Zhang、Ming-Yu Yang、Kai-Li Tang、Mengnan Qu、You-Song Ding、Yang Li

  DOI：10.1021/acs.orglett.6b01091

  日期：2016.6.17

  A rare Ru-catalyzed highly selective synthesis of 3,4-dihydroisoquinolines or isoquinolines is accomplished via a redox-divergent hydrogen-retentive or hydrogen-releasing fashion. Notably, high cis-selectivity of 3,4-dihydroisoquinolines is achieved. Potential applications are shown by gram-scale reactions and very concise synthesis of N-containing polycyclic aromatic compounds. Primary mechanistic

  稀有的Ru催化的3,4-二氢异喹啉或异喹啉的高选择性合成是通过氧化还原发散的氢保持或氢释放方式完成的。值得注意的是，实现了3，4-二氢异喹啉的高顺式选择性。克级反应和非常简洁的含氮多环芳族化合物的合成显示了潜在的应用。初步的机理研究表明，主要途径的序列涉及Ru催化的C–H活化，炔烃插入和随后的6π电环化。