1-benzyl-3-methyl-1,4,5,6-tetrahydroindol-2-one | 15174-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-benzyl-3-methyl-1,4,5,6-tetrahydroindol-2-one
• 英文别名: 1-benzyl-3-methyl-5,6-dihydro-1H-indol-2(4H)-one；2-Oxo-3-methyl-1-benzyl-2,4,5,6-tetrahydro-indol；1-Benzyl-3-methyl-1,4,5,6-tetrahydro-2H-indol-2-one；1-benzyl-3-methyl-5,6-dihydro-4H-indol-2-one
• CAS: 15174-76-2
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: SFZORKUAWRFCQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-methyl-1,4,5,6-tetrahydroindol-2-one 在 N-氯代丁二酰亚胺 、 吡啶盐酸盐 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.17h， 生成 1-benzyl-3-methyl-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  Giannangeli, M.; Baiocchi, L., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 891 - 895

  摘要：

  DOI：
• 作为产物：
  描述：

  N-benzylcyclohexylimine 在 copper diacetate 、 镍 、 溶剂黄146 、 三乙胺 作用下， 以 甲苯 、 叔丁醇 为溶剂， 反应 3.0h， 生成 1-benzyl-3-methyl-1,4,5,6-tetrahydroindol-2-one
  参考文献：
  名称：

  Cassayre, Jérôme; Dauge, Delphine; Zard, Samir Z., Synlett, 2000, # 4, p. 471 - 474

  摘要：

  DOI：

文献信息

• TiCl₄-<i>n</i>-Bu₃N-mediated cascade annulation of ketones with α-ketoesters: a facile synthesis of highly substituted fused γ-alkylidene-butenolides
  作者：Megha N. Palange、Rajesh G. Gonnade、Ravindar Kontham

  DOI：10.1039/c9ob00649d

  日期：——

  to biologically relevant natural products were prepared from readily accessible ketone and α-ketoester building blocks. The highly step-economic cascade nature, good substrate scope, easy access to complex products with good to excellent yields, gram-scalability, demonstration of synthetic utility, and unambiguous structural confirmation through X-ray crystallography analyses and analogy are the salient

  据报道，使用酮与α-酮酸酯的直接环合反应来合成高度取代的稠合γ-亚烷基丁烯化物的简便方法是通过TiCl4-n-Bu3N介导的羟醛加成，然后进行分子内烯醇-内酯化/环化级联反应进行的。从易于获得的酮和α-酮酸酯结构单元中制备与生物相关天然产物有关的6-5、7-5和8-5稠合的双环γ-亚烷基丁烯化物和高度取代的单环类似物。该产品的显着特点是高度阶梯经济的级联性质，良好的底物范围，容易获得具有优良至优异收率的复杂产品，克可缩放性，证明了合成效用以及通过X射线晶体学分析和类似物明确的结构确认。工作。
• Solid-Supported Copper Catalysts for Atom-Transfer Radical Cyclizations:  Assessment of Support Type and Ligand Structure on Catalyst Performance in the Synthesis of Nitrogen Heterocycles
  作者：Andrew J. Clark、Joanna V. Geden、Stephen Thom

  DOI：10.1021/jo0521605

  日期：2006.2.1

  A range of solid supported pyridinemethanimine 9-11 and polyamine 12-15 ligands have been prepared on silica, polystyrene, and JandaJel supports. The CuCl and CuBr complexes of these supported ligands have been used to assess both the effect of the ligand type and the nature of the support upon a representative range of copper-mediated atom transfer 5-exo-trig 6, 24-25, 5-exo-dig 26, 4-exo-trig 28, and 5-endo-trig 27, 38 radical cyclizations to give nitrogen heterocycles. In addition, the effect of the nature of the support on the stereochemical outcome of the 5-exo cyclization of 25 has been probed. Generally, it was found that the type of support (e.g., polystyrene, silica, or JandaJel) had very little effect upon the efficiency and selectivity of the processes but that the nature of the ligand type immobilized was the important factor. Thus, the 5-exo cyclization of 6 and 24-26 proceeded more rapidly with the PMI ligands 9-11, whereas 4-exo cyclizations 28 and 5-endo, radical polar crossover reactions 27 and 38 proceeded more efficiently with the JJ-TEDETA ligand 15. The efficiency of the supported ligands was also compared to their solution counterparts 4 and 5. The reusability of P-PMDETA ligand system 13 was assessed in the cyclization of 6.