N-chloro-sec-butylamine | 52615-84-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-chloro-sec-butylamine
• 英文别名: N-Chloro-sec-butylamine；N-chlorobutan-2-amine
• CAS: 52615-84-6
• 化学式: C₄H₁₀ClN
• 分子量: 107.583
• InChiKey: FCIVVUAMOUYYBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-chloro-sec-butylamine 以 sodium hydroxide 为溶剂， 生成 丁酮
  参考文献：
  名称：

  Kinetic study of the decomposition ofN-chloramines

  摘要：

  DOI：

  10.1002/(sici)1099-1395(199607)9:7<447::aid-poc778>3.0.co;2-x
• 作为产物：
  描述：

  仲丁胺 在 N-氯代丁二酰亚胺 作用下， 反应 0.5h， 生成 N-chloro-sec-butylamine
  参考文献：
  名称：

  使用烷基胺的芳烃的实际和区域选择性胺化。

  摘要：

  用于制备芳香胺的碳-氮键的形成是全球范围内为生产高价值材料而进行的前五项反应之一，从原料化学品到药物和聚合物不等。由于这种普遍性和多样性，其制备方法影响了学术界和工业界的整个化学合成过程。通常，这些分子是通过逐步引入反应性手柄代替芳香族CH键（即硝基，卤素或硼酸）和随后的功能化或交叉偶联而组装而成的。在这里，我们表明，芳烃胺可以使用光催化作用，通过芳烃和烷基胺的直接反应来构建，而无需进行预功能化。该过程可以轻松准备高级构建基块，容忍的功能范围很广，并且可以通过批处理流协议来实现多克规模。通过对几种药物，农药，肽，手性催化剂，聚合物和有机金属配合物的修饰，证明了该策略作为后期功能化平台的优点。

  DOI：

  10.1038/s41557-019-0254-5

文献信息

• Titanium-Mediated Amination of Grignard Reagents Using Primary and Secondary Amines
  作者：Timothy J. Barker、Elizabeth R. Jarvo

  DOI：10.1002/anie.201103700

  日期：2011.8.29

  N‐chlorosuccinimide (NCS) was employed as the oxidant in the synthesis of aniline derivatives using the title transformation (see scheme). Functionalization was well tolerated on both the amine and Grignard reagent. An androgen receptor agonist and several analogues were synthesized to demonstrate the utility of this method.

  制作，然后破坏它：使用标题转化法，在苯胺衍生物的合成中使用N-氯代琥珀酰亚胺（NCS）作为氧化剂（参见方案）。胺和格氏试剂均具有良好的功能性。雄激素受体激动剂和几种类似物被合成以证明该方法的实用性。
• [Cp*RhCl2]2-catalyzed ortho-C–H bond amination of acetophenone o-methyloximes with primary N-chloroalkylamines: convenient synthesis of N-alkyl-2-acylanilines
  作者：Ka-Ho Ng、Zhongyuan Zhou、Wing-Yiu Yu

  DOI：10.1039/c3cc42937g

  日期：——

  Rh(III)-catalyzed aromatic C–H amination of acetophenone o-methyloximes with primary N-chloroalkylamines was developed, and the arylamine products were obtained in up to 92% yield. The reaction probably involves rate-limiting electrophilic C–H bond cleavage (kH/kD = 2).

  开发了 Rh（III）催化的邻甲基苯乙酮肟与伯基 N-氯烷基胺的芳香 CâH 氨基化反应，得到的芳基胺产物收率高达 92%。该反应可能涉及限速亲电 CâH 键裂解（kH/kD = 2）。
• Direct determination of chlorination products of organic amines using membrane introduction mass spectrometry
  作者：T. Kotiaho、M. J. Hayward、R. G. Cooks

  DOI：10.1021/ac00017a025

  日期：1991.9.1

  Direct analysis of organic chloramines in low concentrations in aqueous solutions is achieved by membrane introduction mass spectrometry. Tandem mass spectrometry allows structures of the chlorination products to be determined and shows that nitrogen chlorination occurs for aliphatic amines and ring chlorination for aniline. Monochlorination of aniline occurs mainly at the ortho position, while dichlorination yields 20-35% diortho and 80-65% ortho-para substitution products. Depending on the reaction conditions, the actual chlorination reagent can be chloramine, hypochlorous acid, and possibly chlorine. The high ortho chlorination yields of aniline are explained by a mechanism in which chlorination occurs first at the nitrogen atom with subsequent intramolecular rearrangement to the ortho position in analogy to rearrangement of the nitro group in N-nitro aromatic amines. Using flow injection analysis procedures, it is possible to follow in an on-line fashion reactions that yield (or remove) organic chloramines at sub parts per million levels.
• Chemistry of organic chloramines. Formation of arenesulfonamides by derivatization of organic chloramines with sodium arenesulfinates
  作者：Frank E. Scully、Katherine Bowdring

  DOI：10.1021/jo00338a005

  日期：1981.12
• Kinetics of the formation, decomposition, and disproportionation reactions of<i>N</i>-chlorobutylamines
  作者：Juan M. Antelo、Florencio Arce、Marí C. Castro、Juan Crugeiras、Juan C. Pérez-Moure、Pilar Rodríguez

  DOI：10.1002/kin.550270709

  日期：1995.7

  AbstractThe formation ofN‐chlorobutylamines is a reaction of order one with respect to hypochlorite and amine, and order −1 with respect to OH−. Kinetic studies show thatN‐chlorobutylamines undergo decomposition in basic aqueous media, and disproportination (with formation ofN,N‐dichloramines) in acidic media, mechanisms are put forward for both these processes. © 1995 John Wiley & Sons, Inc.