2-(3-bromophenyl)-1-(toluene-4-sulfonyl)-azetidine | 824390-92-3

• 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: 2-(3-bromophenyl)-1-(toluene-4-sulfonyl)-azetidine
• 英文别名: 2-(3-bromophenyl)-1-tosylazetidine；2-(3-bromophenyl)-N-tosylazetidine；Azetidine, 2-(3-bromophenyl)-1-[(4-methylphenyl)sulfonyl]-；2-(3-bromophenyl)-1-(4-methylphenyl)sulfonylazetidine
• CAS: 824390-92-3
• 化学式: C₁₆H₁₆BrNO₂S
• 分子量: 366.279
• InChiKey: HSPIVCUANDUTER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-(3-bromophenyl)-1-(toluene-4-sulfonyl)-azetidine 在 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以62%的产率得到N-[3-(3-Bromo-phenyl)-3-iodo-propyl]-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  合成2-芳基-N-甲苯磺酸氮杂环丁烷及其ZnX 2（X = I，OTf）的便捷合成途径：区域选择性亲核开环反应：γ-碘胺和四氢嘧啶的合成

  摘要：

  已经描述了制备各种2-芳基-N-甲苯磺酰基氮杂环丁烷的通用且方便的合成途径。已经实现了它们的ZnX 2（X = I，OTf）介导的与卤化物的亲核开环和与各种腈的[4 + 2]环加成反应，分别以良好或优异的收率提供了γ-碘胺和取代的四氢嘧啶。提出了环加成反应的机理。

  DOI：

  10.1016/j.tetlet.2006.05.058
• 作为产物：
  描述：

  (E)-N-(3-溴苯亚甲基)-4-甲基苯磺酰胺 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 26.0h， 生成 2-(3-bromophenyl)-1-(toluene-4-sulfonyl)-azetidine
  参考文献：
  名称：

  2-Aryl-N-tosylazetidines as Formal 1,4-Dipoles for [4 + 2] Cycloaddition Reactions with Nitriles:  An Easy Access to the Tetrahydropyrimidine Derivatives

  摘要：

  [Graphics]A new synthetic route to 2-aryl-N-tosyl azetidines has been developed starting from N-tosylarylaldimines in two steps in an overall yield of 63-70%. A formal [4 + 2] cycloaddition of these 2-aryl-N-tosylazetidines with nitriles in the presence of BF3.OEt2 has been described for the synthesis of substituted tetrahydropyrimidines. It is proposed that the reaction proceeds in Ritter fashion.

  DOI：

  10.1021/ol048161l

文献信息

• Lewis Acid-Mediated Unprecedented Ring-Opening Rearrangement of 2-Aryl-<i>N</i>-tosylazetidines to Enantiopure (<i>E</i>)-Allylamines
  作者：Manas K. Ghorai、Amit Kumar、Kalpataru Das

  DOI：10.1021/ol7023218

  日期：2007.12.1

  of 2-aryl-N-tosylazetidines in polar and coordinating solvents followed by an unprecedented rearrangement to substituted achiral and chiral (E)-allylamines (ee >99%) is reported. The methodology has been applied for the synthesis of gamma-unsaturated-beta-amino acids. A plausible mechanism for the rearrangement is also described.

  Cu（OTf）2介导的在极性和配位溶剂中2-芳基-N-甲苯磺酰氮杂环丁烷的开环高效开环策略，然后空前重排成取代的非手性和手性（E）-烯丙胺（ee> 99％），这是一种高效的策略报告。该方法已用于合成γ-不饱和β-氨基酸。还描述了用于重新布置的合理机制。
• An efficient synthetic route to substituted tetrahydropyrimidines by Cu(OTf)2-mediated nucleophilic ring-opening followed by the [4+2] cycloaddition of N-tosylazetidines with nitriles
  作者：Manas K. Ghorai、Kalpataru Das、Amit Kumar

  DOI：10.1016/j.tetlet.2008.12.035

  日期：2009.3

  A highly efficient strategy for Cu(OTf)2-mediated SN2 type nucleophilic ring-opening followed by the [4+2] cycloaddition reactions of a number of 2-aryl-N-tosylazetidines with nitriles to afford a variety of substituted tetrahydropyrimidines in excellent yields is reported. The resulting tetrahydropyrimidines could easily be transformed into synthetically important 1,3-diamines by acid-catalyzed hydrolysis

  Cu（OTf）2介导的S N 2型亲核开环的高效策略，然后进行许多2-芳基-N-甲苯磺酰氮杂环丁烷与腈的[4 + 2]环加成反应，从而得到各种取代的四氢嘧啶据报道产量极高。所得的四氢嘧啶可通过酸催化的水解容易地转化为合成上重要的1，3-二胺。该策略已扩展到由对映纯二取代的氮杂环丁烷合成对映体纯的四氢嘧啶。反应通过我们之前提出的S N 2型机理进行。
• BF3·OEt2 catalyzed base-free regiospecific ring opening of N-activated azetidines with (E)-1-arylidene-2-arylhydrazines
  作者：Ranadeep Talukdar

  DOI：10.1007/s13738-018-1489-6

  日期：2019.1

  for synthesis of larger molecules. The first report of regiospecific addition of hydrazones to the benzylic position of aryl azetidines to afford high yields of important hydrazonyl amine derivatives is described herein. A new C–N bond forms in this reaction scheme. The reactions proceed at stellar rates in presence of only 5 mol% of BF3·OEt2 Lewis acid without the need of any base. The reaction requires

  摘要对于有机化学家来说，建立C–N键始终是一个有趣的挑战。氮杂环丁烷是合成较大分子的重要的含氮结构单元。本文描述了将specific啶的区域特异性加成到芳基氮杂环丁烷的苄基位置上以提供高产率的重要的肼基胺衍生物的第一个报道。在该反应方案中形成了一个新的C–N键。在仅5mol％的BF 3 ·OEt 2路易斯酸存在下，反应以恒星速率进行，不需要任何碱。该反应需要易于合成的试剂和非常温和的条件。该报告是一种有用的方法，可以合成含有一个或多个N–N键的生物活性天然产物的组成部分。 图形概要描述了氮杂环丁烷与各种的无碱基的区域特异性开环，可在很短的时间内合成各种肼基胺。该报告描述了肼的苯胺N-官能化与平滑的C-N键形成反应。
• Cobalt-catalyzed amination of aziridines and azetidines toward 1,2- and 1,3-diamines
  作者：Ling-Chao Cheng、Zhihua Wang、Xinglei He、Wangfu Liang、Ke-Yin Ye

  DOI：10.1039/d4ob00168k

  日期：——

  A cobalt-catalyzed ring opening, nucleophilic amination of aziridines and azetidines with N-fluorosulfonamides has been established toward a wide range of 1,2- and 1,3-diamine derivatives in moderate to good yields under mild conditions.

  在钴催化下，氮丙啶和氮杂环丁烷与 N-氟磺酰胺发生了开环、亲核胺化反应，在温和的条件下以中等至良好的收率获得了多种 1,2- 和 1,3- 二胺衍生物。
• Lewis Acid-Mediated Highly Regioselective S_N2-Type Ring-Opening of 2-Aryl-<i>N</i>-tosylazetidines and Aziridines by Alcohols
  作者：Manas K. Ghorai、Kalpataru Das、Dipti Shukla

  DOI：10.1021/jo0703294

  日期：2007.7.1

  Lewis acid-mediated highly regioselective S(N)2-type ring-opening of 2-aryl-N-tosylazetidines with alcohols to afford various 1,3-amino ethers in excellent yields with good enantiomeric excess is described. Similar S(N)2-type ring-opening of chiral 2-phenyl-N-tosylaziridine with various alcohols produces the corresponding nonracemic 1,2-amino ethers in excellent yields and good ee. The mechanism of the ring-opening of aziridines and azetidines via an S(N)2 pathway is supported by the formation of nonracemic amino ethers.