(1-azido-3-chloropropyl)benzene | 1332887-38-3

• 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: (1-azido-3-chloropropyl)benzene
• 英文别名: (1-Azido-3-chloropropyl)benzene
• CAS: 1332887-38-3
• 化学式: C₉H₁₀ClN₃
• 分子量: 195.651
• InChiKey: NRDMPJNPTJIJSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-氯-3-苯基丙烷 在 sodium azide 、 N-羟基邻苯二甲酰亚胺 、 ammonium cerium (IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 (1-azido-3-chloropropyl)benzene
  参考文献：
  名称：

  Direct oxidative installation of nitrooxy group at benzylic positions and its transformation into various functionalities

  摘要：

  C-H Nitrooxylation at benzylic positions has been achieved by employing the N-hydroxyphthalimide (NHPI) catalyst/cerium(IV) ammonium nitrate (CAN) reagent system. The nitrooxy groups were demonstrated to function as tentative hydroxy protecting groups, as well as excellent leaving groups for N- and C-substitution reactions. Hence, the present method offers a unique way to synthesize diverse O-. N-, or C-functionalized benzylic compounds from simple alkyl aromatics. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.118

文献信息

• Copper-catalyzed monochloromethylazidation to access transformable terminal alkyl chlorides using stoichiometric BrCH₂Cl
  作者：Ya-Xuan Zhang、Kang-Jie Bian、Ruo-Xing Jin、Chi Yang、Xi-Sheng Wang

  DOI：10.1039/d1cc01751a

  日期：——

  Efficient copper-catalyzed monochloromethylazidation of alkenes with BrCH₂Cl as a stoichiometric chloromethylating source has been developed.

  使用BrCH2Cl作为化学计量量的氯甲基化源，已经开发出了一种高效的铜催化的烯烃单氯甲基叠氮化反应。

• Copper-Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source
  作者：Balaji V. Rokade、Karthik Gadde、Kandikere Ramaiah Prabhu

  DOI：10.1002/ejoc.201500010

  日期：2015.4

  synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has been successfully adapted to the preparation of azides directly from their corresponding alcohols and offers excellent chemoselectivity in the formation

  在2,3-二氯-5存在下，以仲醇、Cu(ClO4)2·6H2O为催化剂，以叠氮化三甲基甲硅烷(TMSN3)为氮源，探索了一种温和、简便的酰胺合成方法。 ,6-二氰基对苯醌 (DDQ) 在环境温度下。该方法已成功地适用于直接从其相应的醇制备叠氮化物，并在 ω-卤代叠氮化物的形成和烯丙醇在苄醇部分存在下的叠氮化中提供出色的化学选择性。此外，该策略为合成可作为 β-氨基酸前体的叠氮化物提供了机会。
• Iron-Catalyzed Chemoselective Azidation of Benzylic Silyl Ethers
  作者：Yoshinari Sawama、Saori Nagata、Yuki Yabe、Kosuke Morita、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1002/chem.201202984

  日期：2012.12.21

  Siloxy groups derived from secondary and tertiary benzyl alcohols can be transformed into azide groups at room temperature using TMSN3 in the presence of an iron catalyst (see scheme; TMS=trimethylsilyl). Secondary and tertiary benzylic silyl ethers can be transformed in the presence of primary silyl ethers, and other reactive functional groups, such as alkyl chlorides, α,β‐unsaturated esters, and aldehydes

  叠氮化：从仲和叔苄基醇衍生的甲硅烷氧基基团可以在室温下使用TMSN转化为叠氮基团3在铁催化剂的存在下（参见流程; TMS =三甲基硅烷基）。可以在伯甲硅烷基醚的存在下转化仲和叔苄基甲硅烷基醚，其他反应性官能团（例如烷基氯，α，β-不饱和酯和醛）在反应条件下是稳定的。
• Chemoselective and Direct Functionalization of Methyl Benzyl Ethers and Unsymmetrical Dibenzyl Ethers by Using Iron Trichloride
  作者：Yoshinari Sawama、Ryota Goto、Saori Nagata、Yuko Shishido、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1002/chem.201303910

  日期：2014.2.24

  tertiary benzylic positions of methyl benzyl ethers or unsymmetrical dibenzyl ethers and is also applicable to direct allylation, alkynylation, and cyanation reactions, as well as the azidation. The present methodologies provide not only a novel chemoselectivity but also the advantage of shortened synthetic steps, due to the direct process without the deprotection of the methyl and benzyl ethers.

  甲基和苄基醚由于其化学稳定性，例如在亲核条件下作为离去基团的甲氧基和苄氧基的反应性低而被广泛用作受保护的醇。我们已经建立了衍生自仲和叔苄醇的化学稳定的甲基和苄基醚的直接叠氮化反应。本发明的叠氮化化学选择地在甲基苄基醚或不对称二苄基醚的仲或叔苄基位置进行，并且还可用于直接烯丙基化，炔化和氰化反应以及叠氮化。本发明的方法不仅提供新颖的化学选择性，而且由于直接方法而没有对甲基和苄基醚进行脱保护，因此提供了缩短的合成步骤的优点。