1-benzyl-1,3,3a,4,5,6-hexahydroindol-2-one | 1214-35-3

• 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-1,3,3a,4,5,6-hexahydroindol-2-one
• 英文别名: N-Benzyl-2-oxo-2,3,3a,4,5,6-hexahydroindol；1-benzyl-3a,4,5,6-tetrahydro-1H-indol-2(3H)-one；1-benzyl-3a,4,5,6-tetrahydro-3H-indol-2-one
• CAS: 1214-35-3
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: KOBQTENANRVURZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  N-benzylcyclohexylimine 在 偶氮二异丁腈 、 三正丁基氢锡 、 三正丁基氟化锡 、 三乙胺 、 sodium iodide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 6.0h， 生成 1-benzyl-1,3,3a,4,5,6-hexahydroindol-2-one
  参考文献：
  名称：

  Is an Iodine Atom Almighty as a Leaving Group for Bu₃SnH-Mediated Radical Cyclization? The Effect of a Halogen Atom on the 5-Endo-trig Radical Cyclization of N-Vinyl-α-halo Amides

  摘要：

  The effect of a halogen atom as a leaving group on Bu3SnH-mediated 5-endo-trig radical cyclization of N-(cyclohex-l-enyl) alpha-halo amides was examined. The cyclization of alpha-chloro amides occurred with a high degree of efficiency, whereas the corresponding alpha-iodo congeners gave only limited quantities of cyclization products. A detailed study revealed that these phenomena could be attributed to the initial conformations of alpha-halo amides. The cyclizing ability of alpha-iodo amides can be restored with Bu3SnCl or Bu3SnF as an additive. The cyclization of an alpha-iodo amide in the presence of Bu3SnF could be applied to a short-step synthesis of lycoranes featuring sequential 5-endo-trig and 6-endo-trig radical cyclizations.

  DOI：

  10.1021/jo020007u

文献信息

• How Do Analogous α-Chloroenamides and α-Iodoenamides Give Different Product Distributions in 5-<i>Endo</i> Radical Cyclizations?
  作者：Dennis P. Curran、David B. Guthrie、Steven J. Geib

  DOI：10.1021/ja8012962

  日期：2008.7.1

  reaction by which the precursor is reductively deiodinated with HI. This side reaction is not available to chlorides, thereby explaining why the chlorides are better precursors in such reactions. The ability of the iodides to provide cyclized products can be largely restored by adding base. The chlorides and iodides then become complementary precursors, with chlorides giving largely cyclized/reduced products

  N-烯基氨基甲酰基甲基自由基的 5-内环化提供 γ-内酰胺自由基，根据试剂和反应条件，γ-内酰胺自由基又会演变为还原或非还原（烯烃）产物。几个小组已经做出令人惊讶的观察结果，即在这种环化中，氯化物是比碘化物更好的自由基前体。这里描述了锡和氢化硅介导的 N-benzyl-2-halo-N-cyclohex-1-enylacetamides 自由基环化的详细研究。直接还原、环化/还原和环化/非还原产物的比例不仅取决于反应条件和还原剂，还取决于前体。排除了基于酰胺旋转异构体效应的前体依赖性产物比率的先前解释。前驱依赖行为被进一步分解为两种不同的影响：(1) 环化/还原产物与环化/非还原产物的比例取决于自由基前体与产物γ-内酰胺自由基反应与氢化锡竞争的能力（碘化物可以竞争，氯化物不能），和（ 2) 在碘化物的情况下，大量直接还原（非环化）产物的出现归因于竞争性离子链反应，通过该反应，前体被 HI
• Tin-free visible light photoredox catalysed cyclisation of enamides as a mild procedure for the synthesis of γ-lactams
  作者：Eleonora Fava、Masaki Nakajima、Martin B. Tabak、Magnus Rueping

  DOI：10.1039/c6gc01099g

  日期：——

  A visible light mediated tin-free 5-endo-trig cyclisation of [small alpha]-chloroenamides, leading to synthetically valuable [gamma]-lactams in good yields and high diastereomeric ratios, was developed.

  开发了可见光介导的小α-氯烯酰胺的无锡5-内-trig环化反应，从而以高收率和高非对映体比率产生了合成上有价值的γ-内酰胺。
• Oxidative radical cyclization on enamide systems using n-Bu3SnH and dilauroyl peroxide
  作者：Miguel A. Guerrero、Raymundo Cruz-Almanza、Luis D. Miranda

  DOI：10.1016/s0040-4020(03)00764-6

  日期：2003.6

  Efficient 5-endo and 6-endo oxidative radical cyclizations on enamide systems are described using nBu(3)SnH and dilauroyl peroxide both as initiator and oxidant. Dibenzoyl peroxide and dicumyl peroxide were also tested in the same reaction and the product yields were very similar to those obtained with dilauroyl peroxide. The erythrina ring system was constructed in a two-step sequence featuring this novel process. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Ishibashi; Matsukida; Toyao, Synlett, 2000, # 10, p. 1497 - 1499
  作者：Ishibashi、Matsukida、Toyao、Tamura、Takeda

  DOI：——

  日期：——
• Is an Iodine Atom Almighty as a Leaving Group for Bu₃SnH-Mediated Radical Cyclization? The Effect of a Halogen Atom on the 5-Endo-trig Radical Cyclization of <i>N</i>-Vinyl-α-halo Amides
  作者：Osamu Tamura、Hana Matsukida、Atsushi Toyao、Yoshifumi Takeda、Hiroyuki Ishibashi

  DOI：10.1021/jo020007u

  日期：2002.8.1

  The effect of a halogen atom as a leaving group on Bu3SnH-mediated 5-endo-trig radical cyclization of N-(cyclohex-l-enyl) alpha-halo amides was examined. The cyclization of alpha-chloro amides occurred with a high degree of efficiency, whereas the corresponding alpha-iodo congeners gave only limited quantities of cyclization products. A detailed study revealed that these phenomena could be attributed to the initial conformations of alpha-halo amides. The cyclizing ability of alpha-iodo amides can be restored with Bu3SnCl or Bu3SnF as an additive. The cyclization of an alpha-iodo amide in the presence of Bu3SnF could be applied to a short-step synthesis of lycoranes featuring sequential 5-endo-trig and 6-endo-trig radical cyclizations.