N-(2-bromoethyl)-N-(1-buten-3-yl)-p-toluenesulfonamide | 145593-61-9

• 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-(2-bromoethyl)-N-(1-buten-3-yl)-p-toluenesulfonamide
• 英文别名: N-(2-bromoethyl)-N-(but-3-en-2-yl)-4-methylbenzenesulfonamide；N-(2-bromoethyl)-N-but-3-en-2-yl-4-methylbenzenesulfonamide
• CAS: 145593-61-9
• 化学式: C₁₃H₁₈BrNO₂S
• 分子量: 332.261
• InChiKey: DMRKZQBOOYTMBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-bromoethyl)-N-(1-buten-3-yl)-p-toluenesulfonamide 在 三正丁基氢锡 作用下， 反应 1.0h， 生成 (2R,3R)-2,3-Dimethyl-1-(toluene-4-sulfonyl)-pyrrolidine 、 (2R,3S)-2,3-Dimethyl-1-(toluene-4-sulfonyl)-pyrrolidine
  参考文献：
  名称：

  Highly stereoselective radical cyclization: copper or ruthenium-catalyzed preparation of cis- and trans-.beta.,.gamma.-dialkyl .gamma.-lactams from acyclic N-allyltrichloroacetamide derivatives

  摘要：

  DOI：

  10.1021/jo00280a011
• 作为产物：
  描述：

  N-(叔丁氧羰基)对甲苯磺酰胺 在 偶氮二甲酸二异丙酯 、 caesium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 17.0h， 生成 N-(2-bromoethyl)-N-(1-buten-3-yl)-p-toluenesulfonamide
  参考文献：
  名称：

  通过直接的C–H活化引发的钴催化串联自由基环化/ C–C偶联

  摘要：

  钴-N-杂环卡宾催化剂促进由螯合辅助的芳烃CH-C活化引发的甲苯磺酰胺系的溴代烯烃与芳基NH的亚胺之间的串联自由基环化/ CC偶联反应，得到3-（芳基甲基）吡咯烷中高收益的衍生产品。该反应耐受芳基亚胺上的各种取代基以及溴代烯烃底物上的各种修饰。

  DOI：

  10.1021/acs.orglett.9b01846

文献信息

• Ni-catalyzed two-component reductive dicarbofunctionalization of alkenes <i>via</i> radical cyclization
  作者：Yulong Kuang、Xuefeng Wang、David Anthony、Tianning Diao

  DOI：10.1039/c8cc00358k

  日期：——

  A reductive dicarbofunctionalization reaction of alkenes has been developed and applied to the preparation of substituted carbo- and heterocycles. The reaction conditions avoid the use of air-sensitive organometallic reagents, and are compatible with a broad range of bromo-electrophiles and a wide variety of substituents to give cyclic products in excellent yields.

  已经开发了烯烃的还原性双碳官能化反应，并将其用于制备取代的碳环和杂环。反应条件避免了使用对空气敏感的有机金属试剂，并且可与各种溴亲电子试剂和各种取代基兼容，从而以优异的收率得到环状产物。
• 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
• Cobalt-Catalyzed Tandem Radical Cyclization/C–C Coupling Initiated by Directed C–H Activation
  作者：Qiao Sun、Naohiko Yoshikai

  DOI：10.1021/acs.orglett.9b01846

  日期：2019.7.5

  A cobalt–N-heterocyclic carbene catalyst promotes a tandem radical cyclization/C–C coupling reaction between tosylamide-tethered bromo-alkenes and aryl N–H imines initiated by chelation-assisted arene C–H activation, affording 3-(arylmethyl)pyrrolidine derivatives in moderate to good yields. The reaction tolerates a variety of substituents on the aryl imine as well as various modifications on the bromo-alkene

  钴-N-杂环卡宾催化剂促进由螯合辅助的芳烃CH-C活化引发的甲苯磺酰胺系的溴代烯烃与芳基NH的亚胺之间的串联自由基环化/ CC偶联反应，得到3-（芳基甲基）吡咯烷中高收益的衍生产品。该反应耐受芳基亚胺上的各种取代基以及溴代烯烃底物上的各种修饰。
• 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
  作者：Hideo Nagashima、Nobuyasu Ozaki、Masayuki Ishii、Koji Seki、Masayoshi Washiyama、Kenji Itoh

  DOI：10.1021/jo00054a034

  日期：1993.1

  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.