N-(2-cyclohexen-1-yl)-2-iodo-N-methylacetamide | 133165-63-6

• 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-(2-cyclohexen-1-yl)-2-iodo-N-methylacetamide
• 英文别名: N-cyclohex-2-en-1-yl-2-iodo-N-methylacetamide
• CAS: 133165-63-6
• 化学式: C₉H₁₄INO
• 分子量: 279.121
• InChiKey: JDAOOYBZBKBMHY-UHFFFAOYSA-N

物化性质

• 沸点：
  320.3±41.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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-(2-cyclohexen-1-yl)-2-iodo-N-methylacetamide 在 六正丁基二锡 、 碘乙烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 、 苯 为溶剂， 反应 2.0h， 生成 (3aR,7aS)-1-Methyl-1,3,3a,6,7,7a-hexahydro-indol-2-one
  参考文献：
  名称：

  Atom-transfer annulations in heterocycle synthesis. An efficient synthesis of (-)-trachelanthamidine and related ring systems

  摘要：

  DOI：

  10.1021/ja00230a044
• 作为产物：
  描述：

  cyclohex-2-en-1-yl 2,2,2-trichloroacetimidate 在 18-冠醚-6 sodium hydroxide 、 sodium hydride 、 三乙胺 、 sodium iodide 作用下， 以 乙醚 、 乙醇 、 丙酮 、 xylene 为溶剂， 反应 50.5h， 生成 N-(2-cyclohexen-1-yl)-2-iodo-N-methylacetamide
  参考文献：
  名称：

  Effects of temperature on atom transfer cyclization reactions of allylic .alpha.-iodo esters and amides

  摘要：

  Atom-transfer cyclizations of allyl iodoacetates and N-allyl-N-methyliodoacetamides are much more efficient at 80-degrees-C than at 25-degrees-C. At 80-degrees-C, beta-(iodomethyl) lactones and lactams are formed rapidly and in good yield under standard atom-transfer conditions (sunlamp irradiation of iodide and 10% hexabutylditin in benzene for 10-60 min). It is proposed that this temperature effect is responsible for some unusual observations by Jolly and Livinghouse in the cyclization of N-cyclohexenyl-N-methyliodoacetamide. The results suggest that the beneficial effect of temperature arises because an increase in the rate of rotation of the OC-O or OC-N bond in the intermediate radicals begins to convert syn radicals (which cannot cyclize) to anti radicals (which can cyclize). Consistent with this hypothesis, the radical derived from N,N-diallyliodoacetamide (which always has a favorable arrangement for cyclization) closes with excellent efficiency at 25-degrees-C.

  DOI：

  10.1021/jo00008a032

文献信息

• A Novel Approach for the Formation of Carbon−Nitrogen Bonds:  Azidation of Alkyl Radicals with Sulfonyl Azides
  作者：Cyril Ollivier、Philippe Renaud

  DOI：10.1021/ja004129k

  日期：2001.5.1

  Two preparatively attractive methods for the azidation of alkyl radicals are described. Secondary and tertiary alkyl iodides and dithiocarbonates are easily converted into the corresponding azides, either by reaction with ethanesulfonyl azide in the presence of dilauroyl peroxide, or by treatment with benzenesulfonyl azide and hexabutylditin in the presence of a radical initiator. Interestingly, intramolecular

  描述了用于烷基基团叠氮化的两种制备性有吸引力的方法。通过在过氧化二月桂酰存在下与乙磺酰叠氮化物反应，或在自由基引发剂存在下用苯磺酰叠氮化物和六丁基二锡处理，仲和叔烷基碘和二硫代碳酸酯很容易转化为相应的叠氮化物。有趣的是，分子内串联自由基环化-叠氮化过程可以以高产率进行。
• An Efficient and Practical Tin Free Procedure for Radical Iodine Atom-Transfer Reactions
  作者：Cyril Ollivier、Thomas Bark、Philippe Renaud

  DOI：10.1055/s-2000-7603

  日期：——

  Iodine atom-transfer is a non-reductive and very attractive way of performing radical reactions that is usually achieved in the presence of hexaalkyldistannanes. We report here an efficient procedure to run such reactions in the absence of ditin derivatives. The iodine atom transfers are performed via thermal initiation with commercially available and cheap dilauroyl peroxide (DLP). Good yields for intra- and intermolecular addition to alkenes are obtained. One example of aromatic substitution for the synthesis of an indolone derivative using stoichiometric amount of DLP is also reported.

  碘原子转移是进行自由基反应的一种非还原性且极具吸引力的方法，通常是在六烷基二烷烃存在的情况下实现的。我们在此报告一种在没有二丁衍生物的情况下进行此类反应的高效程序。碘原子的转移是通过市售廉价过氧化二月桂酰（DLP）的热引发进行的。在烯烃的分子内和分子间加成反应中获得了良好的产率。此外，还报告了一个使用等量 DLP 合成吲哚酮衍生物的芳香取代实例。
• Formation of Carbon−Nitrogen Bonds via a Novel Radical Azidation Process
  作者：Cyril Ollivier、Philippe Renaud

  DOI：10.1021/ja000673h

  日期：2000.7.1
• Ikeda, Masazumi; Teranishi, Hirotaka; Nozaki, Kohei, Journal of the Chemical Society. Perkin transactions I, 1998, # 10, p. 1691 - 1697
  作者：Ikeda, Masazumi、Teranishi, Hirotaka、Nozaki, Kohei、Ishibashi, Hiroyuki

  DOI：——

  日期：——
• CURRAN, DENNIS P.;TAMINE, JOHN, J. ORG. CHEM., 56,(1991) N, C. 2746-2750
  作者：CURRAN, DENNIS P.、TAMINE, JOHN

  DOI：——

  日期：——