1-cyclohexyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline | 72106-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1-cyclohexyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: (rac)-1-cyclohexyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline；1-cyclohexyl-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline；6,7-dimethoxy-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline；1-Cyclohexyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isochinolin
• CAS: 72106-00-4
• 化学式: C₁₇H₂₅NO₂
• 分子量: 275.391
• InChiKey: WCIGAVRPVAPXAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-cyclohexyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 在 1,10-邻二氮杂菲-5,6-二酮 、 氧气 、 4-甲基苯磺酸吡啶 、 zinc(II) iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以90%的产率得到1-cyclohexyl-3,4-dihydro-6,7-dimethoxyisoquinoline
  参考文献：
  名称：

  Bioinspired Aerobic Oxidation of Secondary Amines and Nitrogen Heterocycles with a Bifunctional Quinone Catalyst

  摘要：

  Copper amine oxidases are a family of enzymes with quinone cofactors that oxidize primary amines to aldehydes. The native mechanism proceeds via an iminoquinone intermediate that promotes high selectivity for reactions with primary amines, thereby constraining the scope of potential biomimetic synthetic applications. Here we report a novel bioinspired quinone catalyst system consisting of 1,10-phenanthroline-5,6-dione/ZnI2 that bypasses these constraints via an abiological pathway involving a hemiaminal intermediate. Efficient aerobic dehydrogenation of non-native secondary amine substrates, including pharmaceutically relevant nitrogen heterocycles, is demonstrated. The ZnI2 cocatalyst activates the quinone toward amine oxidation and provides a source of iodide, which plays an important redox-mediator role to promote aerobic catalytic turnover. These findings provide a valuable foundation for broader development of aerobic oxidation reactions employing quinone-based catalysts.

  DOI：

  10.1021/ja411692v
• 作为产物：
  描述：

  1-cyclohexyl-3,4-dihydro-6,7-dimethoxyisoquinoline 在 甲酸 、 C₃₁H₃₆ClN₂O₂RhS 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 0.1h， 生成 1-cyclohexyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  通过改变甲酸与三乙胺的比例来实现亚胺在水中的不对称转移加氢

  摘要：

  亚胺的不对称转移氢化（ATH）随水中甲酸（F）和三乙胺（T）摩尔比的变化而变化。已显示出F / T比影响还原速率和对映选择性，在具有Rh-（1 S，2 S）-TsDPEN催化剂的亚胺的ATH中，最佳比为1.1 。使用甲醇作为助溶剂可增强还原活性。减少了各种亚胺底物，提供了高收率（94–98％）和良好至优异的对映选择性（89–98％）。与普通的共沸FT系统相比，以1.1 / 1 F / T降低速度更快。

  DOI：

  10.1021/acs.orglett.5b00889

文献信息

• Robust cyclometallated Ir(iii) catalysts for the homogeneous hydrogenation of N-heterocycles under mild conditions
  作者：Jianjun Wu、Jonathan H. Barnard、Yi Zhang、Dinesh Talwar、Craig M. Robertson、Jianliang Xiao

  DOI：10.1039/c3cc44567d

  日期：——

  Cyclometallated Cp*Ir(N∧C)Cl complexes derived from N-aryl ketimines are highly active catalysts for the reduction of N-heterocycles under ambient conditions and 1 atm H2 pressure. The reaction tolerates a broad range of other potentially reducible functionalities and does not require the use of specialised equipment, additives or purified solvent.

  由N-芳基亚胺衍生的环金属化Cp*Ir(N∧C)Cl配合物是在常温常压下对N-杂环进行还原的高度活性催化剂。该反应能容忍多种潜在可还原官能团，无需使用特殊设备、添加剂或纯净溶剂。
• Acceptorless Dehydrogenation of Nitrogen Heterocycles with a Versatile Iridium Catalyst
  作者：Jianjun Wu、Dinesh Talwar、Steven Johnston、Ming Yan、Jianliang Xiao

  DOI：10.1002/anie.201300292

  日期：2013.7.1

  Gas up: A cyclometalated iridium complex is found to catalyze the dehydrogenation of various benzofused N‐heterocycles, thus releasing H2. Driven by as low as 0.1 mol % catalyst, the reaction affords quinolines, indoles, quinoxalines, isoquinolines, and β‐carbolines in high yields.

  放气：发现一种环金属化的铱络合物可催化各种苯并稠合的N-杂环的脱氢反应，从而释放出H 2。在低至0.1 mol％的催化剂的驱动下，该反应可高产率提供喹啉，吲哚，喹喔啉，异喹啉和β-咔啉。
• In Vivo Evaluation of Selective Carbonic Anhydrase Inhibitors as Potential Anticonvulsant Agents
  作者：Elvira Bruno、Maria R. Buemi、Laura De Luca、Stefania Ferro、Anna-Maria Monforte、Claudiu T. Supuran、Daniela Vullo、Giovambattista De Sarro、Emilio Russo、Rosaria Gitto

  DOI：10.1002/cmdc.201500596

  日期：2016.8.19

  excitation, we hypothesized that they could represent the biological target for the development of new anticonvulsant agents. Therefore, for selected isoquinoline sulfonamides, we preliminarily tested their ability to prevent audiogenic seizures in DBA/2 mice. All compounds were evaluated after intraperitoneal administration, and some of them proved to protect the mice against convulsions. Among this series

  癫痫病是一种常见的神经系统疾病，由抑制性和兴奋性神经传递之间的不平衡引起。众所周知，神经元兴奋性与γ-氨基丁酸（GABA）能量去极化有关。HCO 3 -可以通过膜渗透性碳酸酐酶抑制剂抑制依赖的去极化。我们以前鉴定了一些异喹啉磺酰胺作为人类碳酸酐酶II和VII（hCA II和hCA VII）同工型的有效和选择性抑制剂。鉴于hCA II和hCA VII是参与GABA介导的神经元兴奋的特定同工型，我们假设它们可以代表开发新的抗惊厥药的生物学靶标。因此，对于选定的异喹啉磺酰胺，我们初步测试了它们在DBA / 2小鼠中预防音源性癫痫发作的能力。腹膜内给药后对所有化合物进行评估，其中一些化合物被证明可以保护小鼠免于惊厥。在这一系列化合物中，几种衍生物显示出对目标碳酸酐酶（即hCA II和hCA VII）具有联合体内功效和抑制作用。具体而言，最有趣的分子是1-（4-氨基苯基）-6,7-二甲氧基-3,4-
• o-Benzenedisulfonimide as a reusable acid catalyst for an easy, efficient, and green synthesis of tetrahydroisoquinolines and tetrahydro-β-carbolines through Pictet–Spengler reaction
  作者：Margherita Barbero、Stefano Bazzi、Silvano Cadamuro、Stefano Dughera

  DOI：10.1016/j.tetlet.2010.09.149

  日期：2010.12

  tetrahydro-β-carbolines, using the Pictet–Spengler reaction, was carried out in the presence of a catalytic amount of o-benzenedisulfonimide, which worked as a Brønsted acid organocatalyst. The reaction conditions were mild and green and good target product yields were achieved. The catalyst was easily recovered and purified, ready to be used in further reactions with economic and ecological advantages.

  使用Pictet-Spengler反应，在催化量的邻苯二磺酰亚胺的存在下进行四氢异喹啉和四氢β-咔啉的合成，该邻苯二磺酰亚胺用作布朗斯台德酸有机催化剂。反应条件温和绿色，并获得了良好的目标产物收率。该催化剂易于回收和纯化，准备用于经济和生态优势的进一步反应中。
• [EN] ANTI-ANGIOGENIC COMPOUNDS<br/>[FR] COMPOSÉS ANTIANGIOGÉNIQUES
  申请人：UNIV DUBLIN

  公开号：WO2014012889A1

  公开（公告）日：2014-01-23

  (E)-2-(2-Quinolin-2-yl-propenyl)-phenol, 2-Quinolin-2-yl-ylethynyl-phenol and salts thereof are useful as medicaments, especially for treatment of an angiogenesis-related disease or disorder.

  (E)-2-(2-喹啉-2-基-丙烯基)-苯酚、2-喹啉-2-基-乙炔基-苯酚及其盐类是有用的药物，特别用于治疗与血管生成相关的疾病或紊乱。