1-azido-3-(bromomethyl)benzene | 92001-69-9

• 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: 1-azido-3-(bromomethyl)benzene
• 英文别名: 3-Azidebenzyl bromide；3-azidobenzyl bromide；3-azidobenzylbromide
• CAS: 92001-69-9
• 化学式: C₇H₆BrN₃
• 分子量: 212.049
• InChiKey: OLSFONZMRDMQLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-azido-3-(bromomethyl)benzene 在 sodium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 六甲基二硅氮烷 作用下， 以 1,4-二氧六环 、 氯仿 、 乙腈 为溶剂， 反应 28.0h， 生成 tris(3-azidobenzyl)amine N-oxide
  参考文献：
  名称：

  三脚架三叠氮化物与三磷烷自组装形成的新的大双环三磷叠氮化物和三磷腈

  摘要：

  三（3-叠氮基苄基）胺与1,1,1-三[[（二苯基膦基）甲基]乙烷经三脚架-三脚架偶合的自组装成功进行，得到了手性大环双环三叠氮化物。这些macrobicyclic笼诱导的加热分子氮的一个显着的阶梯式三重挤压，得到三λ 5个-phosphazenes，它保留它们的前体的手性，螺旋桨状的拓扑结构。用邻苯乙基或亚丙基取代一个苄基臂仍使自组装成功。然而，以N-氧化物形式的三胺的枢转氮原子的季铵化阻止了其与三膦的偶联。

  DOI：

  10.1016/j.tet.2006.04.056
• 作为产物：
  描述：

  3-azidobenzyl alcohol 在 三溴化磷 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以95%的产率得到1-azido-3-(bromomethyl)benzene
  参考文献：
  名称：

  Synthesis of Photophore and Fluorophore Modified O-Benzylserine Derivatives

  摘要：

  O-Benzylation of serine is one of the important protection methods for solid phase peptide synthesis. The utilities of the protection group may be indicated that chemical modifications for O-benzylserine will be utilized to make functional peptides on solid phase synthesis. Detailed studies for effective synthesis of photoreactive and fluorophore containing O-benzylserine derivatives without racemization were reported.

  DOI：

  10.3987/com-16-s(s)37

文献信息

• Asymmetric synthesis of 3-azide-4-fluoro-<scp>l</scp>-phenylalanine
  作者：Masaatsu Adachi、Mado Nakajima、Minoru Isobe

  DOI：10.1080/09168451.2014.997185

  日期：2015.5.4

  The asymmetric synthesis of N-Fmoc-protected 3-azide-4-fluoro-l-phenylalanine as a photoactive phenylalanine analog has been achieved by Schöllkopf's alkylation.

  通过Schöllkopf的烷基化反应，可以实现N-Fmoc保护的3-叠氮基4-氟-1-氟-丙氨酸的不对称合成。
• A ‘clicked’ macrocyclic probe incorporating Binol as the signalling unit for the chiroptical sensing of anions
  作者：Marco Caricato、Alessandro Olmo、Claudia Gargiulli、Giuseppe Gattuso、Dario Pasini

  DOI：10.1016/j.tet.2012.07.038

  日期：2012.9

  detection of halide anions, with the Binol moiety acting as the CD signalling unit. The macrocycle is conveniently synthesized using CuAAC ‘click’ reactions in the cyclization step; this methodology installs 1,2,3-triazole moieties within the macrocyclic backbone, able to directionally bind anions by means of CH⋯X– hydrogen bonds. 1H NMR complexation studies in CDCl3 reveal weak binding to halide and aliphatic

  我们描述了一种用于检测卤化物阴离子的大环手性传感器，其中Binol部分充当CD信号单元。在环化步骤中，使用CuAAC“点击”反应可方便地合成大环；这种方法在大环骨架中安装了1,2,3-三唑部分，能够通过CH⋯X –氢键定向结合阴离子。CDCl 3中的1 H NMR络合研究表明与卤化物和脂肪族羧酸根阴离子的结合较弱。但是，卤化物阴离子保留在大环腔中时，能够触发大的手性反应，该反应来自与Binol部分的空间相互作用，从而改变了其二面角，从而调节了其特征性CD标记。
• Design, syntheses and evaluation of 4-oxo-5-cyano thiouracils as SecA inhibitors
  作者：Arpana S. Chaudhary、Jinshan Jin、Weixuan Chen、Phang C. Tai、Binghe Wang

  DOI：10.1016/j.bmc.2014.11.017

  日期：2015.1

  Protein translocation is essential for bacterial survival and the most important translocation mechanism is the secretion (Sec) pathway in which SecA is a central core driving force. Thus targeting SecA is a promising strategy for developing novel antibacterial therapeutics. Herein, we report the syntheses and evaluation of a series of nearly 60 4-oxo-5-cyano thiouracil derivatives based upon our previously reported core pyrimidine structure. Introduction of polar group such as -N-3 and linker groups such as -CH2-O- enhanced the potency several fold. Apart from being potential antibacterial agents, these inhibitors can be indispensable tools for biologists to probe the mechanism of protein translocation via the SecA machinery in bacteria. Published by Elsevier Ltd.
• Mornet, Rene; Leonard, Nelson J.; Theiler, Jane B., Journal of the Chemical Society. Perkin transactions I, 1984, # 5, p. 879 - 885
  作者：Mornet, Rene、Leonard, Nelson J.、Theiler, Jane B.、Doree, Marcel

  DOI：——

  日期：——
• The design and synthesis of YC-1 analogues as probes for soluble guanylate cyclase
  作者：Kirk W. Hering、Jennifer D. Artz、William H. Pearson、Michael A. Marletta

  DOI：10.1016/j.bmcl.2005.10.093

  日期：2006.2

  Soluble guanylate cyclase (sGC) is highly activated in the presence of both YC-1 (1-benzyl-3-(5'-hydroxymethyl-2'-furyl)indazole) and CO. In this report, the design, synthesis, and activity (i.e., sGC activation) of photolabile analogues of 3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole (YC-1) are presented. Initial results with 6-azido-3-(5'-hydroxymethyl-2-furyl)-1-benzylindazole led to the synthesis of a tritium-labeled analogue. When photoactivated, this analogue labeled the alpha-subunit of sGC. (c) 2005 Elsevier Ltd. All rights reserved.