N-(Cyclohex-1-enyl)-N-methyl-α-chloroacetamide | 70383-15-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(Cyclohex-1-enyl)-N-methyl-α-chloroacetamide
• 英文别名: 2-chloro-N-(cyclohex-1-enyl)-N-methylacetamide；2-Chlor-N-(1-cyclohexen-1-yl)-N-methylacetamid；2-chloro-N-(cyclohexen-1-yl)-N-methylacetamide
• CAS: 70383-15-2
• 化学式: C₉H₁₄ClNO
• 分子量: 187.669
• InChiKey: HIIIMCCSXPPKIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  45-46 °C(Solv: hexane (110-54-3))
• 沸点：
  305.5±31.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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-(Cyclohex-1-enyl)-N-methyl-α-chloroacetamide 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium iodide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 2.0h， 生成 N-(cyclohex-1-enyl)-N-methylacetamide
  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
• 作为产物：
  描述：

  氯乙酰氯 、 N-cyclohexylidenemethylamine 在 吡啶 作用下， 以 苯 为溶剂， 反应 1.0h， 以26%的产率得到N-(Cyclohex-1-enyl)-N-methyl-α-chloroacetamide
  参考文献：
  名称：

  Sato, Tatsunori; Nakamura, Nobuyuki; Ikeda, Keiko, Journal of the Chemical Society. Perkin transactions I, 1992, # 18, p. 2399 - 2408

  摘要：

  DOI：

文献信息

• Ishibashi; Matsukida; Toyao, Synlett, 2000, # 10, p. 1497 - 1499
  作者：Ishibashi、Matsukida、Toyao、Tamura、Takeda

  DOI：——

  日期：——
• Radical cyclizations of N-vinylic α-chloroacetamides. 5-endo-trig and 4-exo-trig cyclizations
  作者：Hiroyuki Ishibashi、Nobuyuki Nakamura、Tatsunori Sato、Michiyo Takeuchi、Masazumi Ikeda

  DOI：10.1016/s0040-4039(00)74314-0

  日期：1991.4

  Bu3SnH mediated radical cyclizations of N-vinylic alpha-chloroacetamides proceeded in a "disfavored" 5-endo-trig manner to give five-membered lactams. Some exceptions where the 4-exo cyclization predominates are also described.
• CHUPP J. P.; METZ S., J. HETEROCYCL. CHEM., 1979, 16, NO 1, 65-71
  作者：CHUPP J. P.、 METZ S.

  DOI：——

  日期：——
• Sato, Tatsunori; Nakamura, Nobuyuki; Ikeda, Keiko, Journal of the Chemical Society. Perkin transactions I, 1992, # 18, p. 2399 - 2408
  作者：Sato, Tatsunori、Nakamura, Nobuyuki、Ikeda, Keiko、Okada, Michiyo、Ishibashi, Hiroyuki、Ikeda, Masazumi

  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.