N-benzyl-2-chloro-N-(cyclohex-2-enyl)acetamide | 105706-89-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-2-chloro-N-(cyclohex-2-enyl)acetamide
• 英文别名: N-benzyl-N-chloroacetyl-2-cyclohexenylamine；N-benzyl-2-chloro-N-cyclohex-2-en-1-ylacetamide
• CAS: 105706-89-6
• 化学式: C₁₅H₁₈ClNO
• 分子量: 263.767
• InChiKey: VJLDZTRGPIYYBA-UHFFFAOYSA-N

物化性质

• 沸点：
  407.7±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  N-benzyl-2-chloro-N-(cyclohex-2-enyl)acetamide 在 palladium on activated charcoal 、 四(三苯基膦)钯 1,8-双二甲氨基萘 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 16.0h， 生成 1-苄基-3H-吲哚-2-酮
  参考文献：
  名称：

  New synthesis of heterocycles by use of palladium catalyzed cycli zation of α-haloamide with internal double bond

  摘要：

  DOI：

  10.1016/s0040-4020(01)91346-8
• 作为产物：
  描述：

  3-溴环己烯 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.33h， 生成 N-benzyl-2-chloro-N-(cyclohex-2-enyl)acetamide
  参考文献：
  名称：

  通过近正电荷进行酰胺的交换和构象固定

  摘要：

  通常以顺式/反式混合物形式存在的叔酰胺可通过将正电荷置于酰胺羰基附近来有效地转变为顺式构象。该作用用于制备顺式构型的脯氨酰胺，并促进强烈依赖于旋转异构体的自由基环化。

  DOI：

  10.1002/anie.201502474

文献信息

• Radical, One-Step Approach to <i>o</i>-Chlorophenyl Thioethers from Xanthates. A Rapid Access to Vinylsilanes
  作者：Matthieu Corbet、Zorana Ferjančić、Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1021/ol801348u

  日期：2008.8.21

  Xanthates have been readily converted into o-chlorophenyl thioethers using a one-step procedure conducted under radical conditions. In some selected cases, these aryl thioethers were successfully oxidized to the corresponding sulfoxides and sulfenic acid elimination afforded the corresponding vinylsilanes.
• 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.
• Ishibashi; Matsukida; Toyao, Synlett, 2000, # 10, p. 1497 - 1499
  作者：Ishibashi、Matsukida、Toyao、Tamura、Takeda

  DOI：——

  日期：——
• New synthesis of heterocycles by use of palladium catalyzed cycli zation of α-haloamide with internal double bond
  作者：Miwako Mori、Nana Kanda、Izumi Oda、Yoshio Ban

  DOI：10.1016/s0040-4020(01)91346-8

  日期：1985.1
• Switching and Conformational Fixation of Amides Through Proximate Positive Charges
  作者：Amelie L. Bartuschat、Karina Wicht、Markus R. Heinrich

  DOI：10.1002/anie.201502474

  日期：2015.8.24

  Tertiary amides, which usually occur as cis/trans mixtures, can be effectively shifted to the cis conformation by placing a positive charge in close proximity to the amide carbonyl. This effect was used to prepare cis‐configured prolyl amides and to facilitate a strongly rotamer‐dependent radical cyclization.

  通常以顺式/反式混合物形式存在的叔酰胺可通过将正电荷置于酰胺羰基附近来有效地转变为顺式构象。该作用用于制备顺式构型的脯氨酰胺，并促进强烈依赖于旋转异构体的自由基环化。