3,4-diethyl-1-methylisoquinoline | 1198575-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3,4-diethyl-1-methylisoquinoline
• CAS: 1198575-49-3
• 化学式: C₁₄H₁₇N
• 分子量: 199.296
• InChiKey: BIJCWQOFSKFBJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  在 ammonium acetate 、 溶剂黄146 作用下， 反应 16.0h， 以14 mg的产率得到3,4-diethyl-1-methylisoquinoline
  参考文献：
  名称：

  Activating Group Recycling in Action: A Rhodium-Catalyzed Carbothiolation Route to Substituted Isoquinolines

  摘要：

  A new rhodium(l) catalyst allows practical and efficient alkyne carbothiolation reactions to be achieved on synthetically useful ketone-bearing aryl methyl sulfides. The carbothiolation adducts, featuring a 'recycled methyl sulfide' activating group, are convenient precursors to highly substituted isoquinolines.

  DOI：

  10.1021/ol402650q

文献信息

• <i>N</i>-Tosylhydrazone directed annulation <i>via</i> C–H/N–N bond activation in Ru(<scp>ii</scp>)/PEG-400 as homogeneous recyclable catalytic system: a green synthesis of isoquinolines
  作者：Dewal S. Deshmukh、Bhalchandra M. Bhanage

  DOI：10.1039/c8ob01082j

  日期：——

  of isoquinolines using Ru(II)/PEG-400 as a homogeneous recyclable catalytic system has been demonstrated. N-Tosylhydrazone, a rarely explored directing group, has been successfully employed for an annulation type of reaction with alkynes via C–H/N–N activation. A short reaction time with a simple extraction procedure, a wide substrate scope with high yields of products, easily prepared substrates, biodegradable

  已经证明了使用Ru（II）/ PEG-400作为均相可循环催化体系合成异喹啉的绿色可持续方法。N-甲苯磺酰，是一个很少探索的指导基团，已成功地用于通过C–H / N–N活化与炔烃形成环型反应。反应时间短，萃取步骤简单，底物范围广，产品收率高，易于制备的底物，可生物降解的溶剂以及可扩展至克级的可扩展性，可提高拟议方案的效率和可持续性。此外，昂贵的基于钌的均相催化体系可重复使用多达四个连续循环，而不会损失其活性。
• Easy Access to 1-Amino and 1-Carbon Substituted Isoquinolines <i>via</i> Cobalt-Catalyzed CH/NO Bond Activation
  作者：Krishnamoorthy Muralirajan、Ramajayam Kuppusamy、Sekar Prakash、Chien-Hong Cheng

  DOI：10.1002/adsc.201501056

  日期：2016.3.3

  A green atom‐economical method for the synthesis of highly functionalized 1‐amino and 1‐carbon substituted isoquinolines from the reaction of N′‐hydroxybenzimidamides and aryl ketoximes, respectively, with alkynes via pentamethylcyclopentadienylcobalt(III)‐catalyzed CH/NO bond activation is described. The external oxidant‐free annulation reaction uses the =NOH moiety in N′‐hydroxybenzimidamides or

  用于从反应高度官能化的1-氨基和1-碳取代的异喹啉的合成绿色原子的经济的方法N'- hydroxybenzimidamides和芳基酮肟，分别与炔烃经由pentamethylcyclopentadienylcobalt（III）催化Ç  H /Ñ 描述了O键活化。外部无氧化剂环化反应在N'-羟基苯甲酰胺或N中使用= NOH部分-芳族酮肟为导向基团和内部氧化剂。该第一行过渡金属催化的环化反应可作为异喹啉合成的有效替代方法，因为水是唯一的副产物，且贵金属例如铑（III），铱（III），钯（II）和钌是贵金属（II）不是必需的。反应的进行通过Ç  ħ活化，炔插入，还原消除，和N  Ò活化。
• Hydroxylamine-<i>O</i> -Sulfonic Acid (HOSA) as a Redox-Neutral Directing Group: Rhodium Catalyzed, Additive Free, One-Pot Synthesis of Isoquinolines from Arylketones
  作者：Pragati Biswal、Bedadyuti Vedvyas Pati、Rajesh Chebolu、Asit Ghosh、P. C. Ravikumar

  DOI：10.1002/ejoc.201901825

  日期：2020.2.28

  A new reactivity of hydroxylamine‐O‐sulfonic acid (HOSA) has been demonstrated as redox‐neutral directing group for rhodium‐catalyzed one‐pot synthesis of diverse isoquinolines. This protocol reveals the utility of HOSA as a dircting group for the addditive free C–H/N–O annulations. Moreover, the in situ cleavage of the directing group reduces one step making it as a step‐economical process.

  羟胺-O-磺酸（HOSA）的新反应性已被证明是氧化还原中性的导向基团，用于铑催化的一锅合成各种异喹啉。该协议揭示了HOSA作为加性自由C–H / N–O环的一个转向基的效用。此外，定向基团的原位切割减少了一个步骤，使其成为一个步骤经济的过程。
• Cp*Co(<scp>iii</scp>)-catalyzed annulation of azines by C–H/N–N bond activation for the synthesis of isoquinolines
  作者：Dewal S. Deshmukh、Prashant A. Yadav、Bhalchandra M. Bhanage

  DOI：10.1039/c9ob00174c

  日期：——

  and external oxidant free approach has been disclosed for the synthesis of isoquinolines. Azines were employed for annulation reactions with alkynes via sequential C–H/N–N bond activation using an air-stable cobalt catalyst. The method takes advantage of the incorporation of both the nitrogen atoms of azines into the desired isoquinoline products, offering the highest atom economy. In addition, the

  在此，已经公开了用于合成异喹啉的有效的，原子经济的和无外部氧化剂的方法。叠氮被用于通过空气稳定的钴催化剂通过连续的C–H / N–N键活化与炔烃进行环化反应。该方法利用了将两个氮原子都掺入所需的异喹啉产物中的优点，从而提供了最高的原子经济性。此外，开发的协议可在外部氧化剂以及无银盐的条件下工作。此外，已建立的方法具有相对较宽的底物范围，具有较高的产品产量和高达克级的可扩展性。
• Rapid and Atom Economic Synthesis of Isoquinolines and Isoquinolinones by C-H/N-N Activation Using a Homogeneous Recyclable Ruthenium Catalyst in PEG Media
  作者：Dewal S. Deshmukh、Neha Gangwar、Bhalchandra M. Bhanage

  DOI：10.1002/ejoc.201900366

  日期：2019.5.15

  An atom‐efficient, rapid, green and sustainable approach has been developed for the synthesis of isoquinolines and isoquinolinones by annulation via C–H/N–N activation using a homogeneous recyclable ruthenium catalyst in PEG media.

  已经开发了一种原子高效，快速，绿色且可持续的方法，用于在PEG介质中使用均相可回收钌催化剂通过C–H / N–N活化进行环化来合成异喹啉和异喹啉酮。