2-(2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)cyclohexanone | 1350479-69-4

• 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: 2-(2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)cyclohexanone
• CAS: 1350479-69-4
• 化学式: C₂₂H₂₅NO₂
• 分子量: 335.446
• InChiKey: MIZVVNBKXROMLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  四氢异喹啉 在 potassium dihydrogenphosphate 、 copper(l) iodide 、 乙二醇 作用下， 以 异丙醇 为溶剂， 反应 48.0h， 生成 (S)-2-((R)-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)cyclohexanone 、 2-(2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)cyclohexanone
  参考文献：
  名称：

  Bifunctional organic sponge photocatalyst for efficient cross-dehydrogenative coupling of tertiary amines to ketones

  摘要：

  一种新型的双功能有机海绵光催化剂可以在水中实现三级胺与酮的高效偶联。使用这种海绵光催化剂也可以实现不对称转化。

  DOI：

  10.1039/c7cc06997a

文献信息

• Dehydrogenative coupling reactions catalysed by Rose Bengal using visible light irradiation
  作者：Yuanhang Pan、Choon Wee Kee、Li Chen、Choon-Hong Tan

  DOI：10.1039/c1gc15489c

  日期：——

  Rose Bengal, an organic dye, was demonstrated to be a photoredox catalyst for dehydrogenative coupling reactions using visible light irradiation. α-Functionalised tertiary amines were obtained with good to excellent yields. Air is essential for this reaction and acts as the terminal oxidant. This is an environmentally friendly C–H functionalisation methodology that avoids the use of metal catalysts and stoichiometric amount of peroxo-compounds.

  玫瑰苯胭脂，一种有机染料，被证明可以作为光氧还原催化剂，通过可见光照射进行脱氢耦合反应。获得了α-功能化的三级胺，收率良好至优异。空气是该反应的必要条件，并充当末端氧化剂。这是一种环保的C–H功能化方法，避免了使用金属催化剂和化学计量的过氧化物。
• Chiral organic contact ion pairs in metal-free catalytic enantioselective oxidative cross-dehydrogenative coupling of tertiary amines to ketones
  作者：Gen Zhang、Yunxia Ma、Shoulei Wang、Weidong Kong、Rui Wang

  DOI：10.1039/c3sc50604e

  日期：——

  A novel chiral organic contact ion-pair catalytic system has been developed for the transition-metal-free catalytic enantioselective oxidative cross-dehydrogenative coupling of tertiary amines to ketones for sp3 C–H functionalization. This new strategy provides an efficient and environmentally friendly way to access diversify optically active C1-alkylated tetrahydroisoquinoline derivatives from simple starting materials under mild conditions.

  我们开发了一种新型手性有机接触离子对催化系统，用于无过渡金属催化叔胺与酮的对映选择性氧化交叉脱氢偶联，以实现 sp3 C-H 功能化。这种新策略为在温和条件下从简单的起始材料中获得具有多种光学活性的 C1-烷基化四氢异喹啉衍生物提供了一种高效、环保的方法。
• Visible‐Light‐Promoted Asymmetric Cross‐Dehydrogenative Coupling of Tertiary Amines to Ketones by Synergistic Multiple Catalysis
  作者：Qi Yang、Long Zhang、Chen Ye、Sanzhong Luo、Li‐Zhu Wu、Chen‐Ho Tung

  DOI：10.1002/anie.201700572

  日期：2017.3.20

  Reported herein is an unprecedented photocatalytic asymmetric cross‐dehydrogenative coupling reaction between tertiary amines and simple ketones, and it proceeds by synergistic multiple catalysis with substoichiometric amounts of a hydrogen acceptor. This process is enabled by a simple chiral primary amine catalyst through the coupling of a catalytic enamine intermediate and an iminium cation intermediate

  本文报道的是叔胺与简单酮之间前所未有的光催化不对称交叉脱氢偶联反应，它是通过亚化学计量的氢受体的协同多重催化而进行的。通过简单的手性伯胺催化剂，通过偶联的Ru / Co催化，由四氢异喹啉衍生物原位生成催化烯胺中间体和亚胺阳离子中间体，可以实现该过程。
• Catalytic Asymmetric Electrochemical Oxidative Coupling of Tertiary Amines with Simple Ketones
  作者：Niankai Fu、Longji Li、Qi Yang、Sanzhong Luo

  DOI：10.1021/acs.orglett.7b00746

  日期：2017.4.21

  Catalytic asymmetric electrochemical C–H functionalization of simple ketones has been developed. The transformation is realized by the combination of electrochemical oxidation and chiral primary amine catalysis. This metal- and oxidant-free method furnishes diverse C1-alkylated tetrahydroisoquinolines in high yields and with excellent enantioselectivities under very mild conditions.

  已经开发了简单的酮的催化不对称电化学C–H功能化。该转化是通过电化学氧化和手性伯胺催化相结合而实现的。这种无金属和氧化剂的方法可在非常温和的条件下以高收率和优异的对映选择性提供各种C1烷基化的四氢异喹啉。
• Asymmetric Organocatalysis and Photoredox Catalysis for the α-Functionalization of Tetrahydroisoquinolines
  作者：Hong Hou、Shaoqun Zhu、Iuliana Atodiresei、Magnus Rueping

  DOI：10.1002/ejoc.201800117

  日期：2018.3.14

  H. H. and S. Z. are grateful to the Chinese Scholarship Council for fellowships. The research leading to these results has received funding from the European Research Council under the European Union's Seventh Framework Programme (FP/2007‐2013)/ ERC Grant Agreement no. 617044 (SunCatChem).

  HH 和 SZ 感谢中国留学基金委提供的奖学金。根据欧盟第七框架计划 (FP/2007-2013)/ERC 赠款协议，导致这些结果的研究已获得欧洲研究理事会的资助。617044 (SunCatChem)。