N-(1-Methyl-allyl)-N-(2,2,2-trichloro-acetyl)-methanesulfonamide | 122722-33-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-(1-Methyl-allyl)-N-(2,2,2-trichloro-acetyl)-methanesulfonamide
• 英文别名: N-but-3-en-2-yl-2,2,2-trichloro-N-methylsulfonylacetamide
• CAS: 122722-33-2
• 化学式: C₇H₁₀Cl₃NO₃S
• 分子量: 294.586
• InChiKey: GIXBQAQQELUDTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(1-Methyl-allyl)-N-(2,2,2-trichloro-acetyl)-methanesulfonamide 以85%的产率得到
  参考文献：
  名称：

  NAGASHIMA, HIDEO;OZAKI, NOBUYASU;SEKI, KOJI;ISHII, MASAYUKI;ITOH, KENJI, J. ORG. CHEM., 54,(1989) N9, C. 4497-4499

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(1-Methyl-allyl)-methanesulfonamide 、 三氯乙酰氯 在 正丁基锂 作用下， 生成 N-(1-Methyl-allyl)-N-(2,2,2-trichloro-acetyl)-methanesulfonamide
  参考文献：
  名称：

  Transition metal-catalyzed radical cyclizations: a low-temperature process for the cyclization of N-protected N-allyltrichloroacetamides to trichlorinated .gamma.-lactams and application to the stereoselective preparation of .beta.,.gamma.-disubstituted .gamma.-lactams

  摘要：

  Cyclizations of N-substituted N-allyltrichloroacetamides, where the substituent is an alkyl, Cbz, Boc, Ts, or Ms group, are catalyzed by a 1:1 mixture of CuCl and bipyridine to give the corresponding beta,gamma-trichlorinated gamma-lactams in high yields. The reactions proceed at temperatures from -78-degrees-C to room temperature. Cyclizations of N-allyltrichloroacetamides of acyclic secondary allylic amines are achieved with good selectivity; the cis/trans ratios of the gamma-lactams formed were dependent on the substituents on the nitrogen atom. The stereochemical outcome is compared with that of free-radical cyclization.

  DOI：

  10.1021/jo00054a034

文献信息

• Highly stereoselective radical cyclization: copper or ruthenium-catalyzed preparation of cis- and trans-.beta.,.gamma.-dialkyl .gamma.-lactams from acyclic N-allyltrichloroacetamide derivatives
  作者：Hideo Nagashima、Nobuyasu Ozaki、Koji Seki、Masayuki Ishii、Kenji Itoh

  DOI：10.1021/jo00280a011

  日期：1989.9