1-benzyl-1-methyl-5,6-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-2(4H)-one | 1566616-94-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 1-benzyl-1-methyl-5,6-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-2(4H)-one
• 英文别名: 3-Benzyl-3-methyl-1-azatricyclo[6.3.1.04,12]dodeca-4,6,8(12)-trien-2-one；3-benzyl-3-methyl-1-azatricyclo[6.3.1.04,12]dodeca-4,6,8(12)-trien-2-one
• CAS: 1566616-94-1
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: XHTGGTSENZXPAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯硼酸 在 tetrafluoroboric acid 、 三氟化硼乙醚 、 copper(II) bis(trifluoromethanesulfonate) 、 间氯过氧苯甲酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 1-benzyl-1-methyl-5,6-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-2(4H)-one
  参考文献：
  名称：

  Copper-Catalyzed Diarylation of Activated Alkenes with Diaryliodonium Salts

  摘要：

  Cu(OTf)(2)-catalyzed diarylation of activated alkenes by using diaryliodonium(III) salts has been developed. With this method, arylated oxindoles can be easily accessed in good yields. Insights into the mechanism of copper-catalyzed arylations are discussed, and the findings are expected to help increase the level of understanding of catalytic arylations with diaryliodonium salts.

  DOI：

  10.1055/s-0033-1339004

文献信息

• Copper-catalyzed bis-arylations of alkenes leading to oxindole derivatives
  作者：Liangliang Shi、Yuyuan Wang、Haijun Yang、Hua Fu

  DOI：10.1039/c4ob00576g

  日期：——

  A simple and practical copper-catalyzed approach to oxindole derivatives by copper-catalyzed bis-arylation of N-alkyl-N-phenylacrylamides with diaryliodonium triflates has been developed under mild conditions, and the method is of tolerance towards some functional groups in the substrates.

  一个简单且实用的铜催化方法已经被开发出来，用于在温和条件下通过铜催化的二芳基化反应合成吲哚衍生物，该方法对底物中的一些官能团具有耐受性。
• <i>Endo</i>/<i>Exo</i>-Controllable Photocyclization by EnT-SET-Switch
  作者：Xian-Peng Cai、Bin-Hong Han、Fu-Tong Cen、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/acs.orglett.3c00837

  日期：2023.4.28

  CBZ6, a redox-neutral non-donor–acceptor-type organo-photocatalyst, presents a strong reductive potential with an oxidative potential of −2.16 V (vs SCE). It can work as a photosensitizer for both single-electron transfer and triplet energy transfer processes. This feature enables site-selective control in the intramolecular hydroarylation of acrylamides. Both 5-exo-trig and 6-endo-trig cyclization

  CBZ6是一种氧化还原中性非供体-受体型有机光催化剂，具有很强的还原电位，氧化电位为 -2.16 V（相对于 SCE）。它可以作为单电子转移和三线态能量转移过程的光敏剂。此功能可以在丙烯酰胺的分子内加氢芳基化中进行位点选择性控制。5- exo -trig 和 6- endo -trig 环化产物均可在温和条件下区域特异性制备。不涉及过渡金属、含卤素试剂或额外的还原剂或氧化剂。该过程为一系列羟吲哚和二氢喹啉酮提供了一种简洁且环境可持续的途径。
• Copper(I)-Catalyzed Aryl or Vinyl Addition to Electron-Deficient Alkenes Cascaded by Cationic Cyclization
  作者：Bing Zhou、Wei Hou、Yaxi Yang、Huijin Feng、Yuanchao Li

  DOI：10.1021/ol500033w

  日期：2014.3.7

  An exoselective copper-catalyzed arylation and vinylation-carbocyclization of electron-deficient alkenes was developed to provide rapid and efficient access to a variety of functionalized 3,3-disubstituted oxindoles. With this method, a highly efficient and concise formal synthesis of (+/-)-physostigmine and (+/-)-physovenine has been completed.