6-methyl-1-oxo-1,2,3,4-tetrahydrophenanthridine 5-oxide | 1449580-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-methyl-1-oxo-1,2,3,4-tetrahydrophenanthridine 5-oxide
• CAS: 1449580-15-7
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: UDXDAOJUCXKAPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.01
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver(I) acetate 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 14.0h， 生成 6-methyl-1-oxo-1,2,3,4-tetrahydrophenanthridine 5-oxide
  参考文献：
  名称：

  碘鎓盐作为Rh（III）催化的CH活化中的碳前体。

  摘要：

  铑（III）催化的C–H底物与碘鎓碘化物的偶联已经实现了各种环状骨架的有效合成，其中碘鎓碘化物已被认为是有效且出色的卡宾前体。该反应系统适用于在轻度和氧化还原中性条件下的sp 2和sp 3 C–H底物。在克规模的反应中，催化剂的负载量可以低至0.5mol％。代表性产品在纳摩尔水平下对人癌细胞具有细胞毒性。

  DOI：

  10.1021/acs.orglett.0c02618

文献信息

• Access to tetrahydrophenanthridine N-oxides via Rh(III)-catalyzed cascade C–H activation/cyclization of cyclic 2-diazo-1,3-diones and aryloximes
  作者：Yinyin Feng、Guanghao Shi、Liwei Xiang、Wangcheng Hu、Xinwei He、Yongjia Shang

  DOI：10.1016/j.tet.2023.133584

  日期：2023.9

  protocol for the synthesis of tetrahydrophenanthridine N-oxides has been achieved from easily available cyclic 2-diazo-1,3-diones with aryloximes. This transformation proceeded through Rh(III)-catalyzed C–H activation and subsequent intramolecular cyclization under mild conditions, and involved the formation of two new bonds (C–C & C–N) in a single reaction vessel for the construction of novel fused isoquinoline

  由容易获得的环状2-重氮-1,3-二酮与芳基肟实现了一种有效且简单的合成四氢菲啶N-氧化物的方案。该转化通过 Rh(III) 催化的 C-H 活化和随后在温和条件下的分子内环化进行，并涉及在单个反应容器中形成两个新键（C-C 和 C-N），用于构建新型稠合化合物异喹啉N-氧化物，唯一的副产物是N 2和H 2 O。值得注意的是，该过程可以轻松地以一毫摩尔规模进行，也可以放大至克规模合成，而不会降低产率百分比。
• Ir(III)-Catalyzed Synthesis of Isoquinoline <i>N</i>-Oxides from Aryloxime and α-Diazocarbonyl Compounds
  作者：Ravindra S. Phatake、Pitambar Patel、Chepuri V. Ramana

  DOI：10.1021/acs.orglett.5b03462

  日期：2016.1.15

  An efficient Ir(III)-catalyzed C-H activation and annulations of aryloxime with a-diazocarbonyl compounds has been developed for the synthesis of substituted isoquinoline N-oxides. The reaction proceeds under mild atmospheric conditions, without any external oxidants and releases N-2 and H2O as the byproducts. In addition, synthetic applications of the N-oxide products have been established by performing further functionalization. An interesting dimeric iridacyclic complex allied through a bis-silver carboxylate bridge has been isolated that efficiently catalyzed the reaction.
• Rh(III)-Catalyzed Synthesis of Multisubstituted Isoquinoline and Pyridine <i>N</i>-Oxides from Oximes and Diazo Compounds
  作者：Zhuangzhi Shi、Dennis C. Koester、Mélissa Boultadakis-Arapinis、Frank Glorius

  DOI：10.1021/ja406338r

  日期：2013.8.21

  Multisubstituted isoquinoline and pyridine N-oxides have been prepared by Rh(III)-catalyzed cyclization of oximes and diazo compounds via aryl and vinylic C-H activation. This intermolecular annulation involving tandem C-H activation, cyclization, and condensation steps proceeds under mild conditions, obviates the need for oxidants, releases N-2 and H2O as the byproducts, and displays a broad substituent scope.