3-azido-5-iodobenzyl alcohol | 528893-97-2

• 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: 3-azido-5-iodobenzyl alcohol
• 英文别名: (3-Azido-5-iodophenyl)methanol；(3-azido-5-iodophenyl)methanol
• CAS: 528893-97-2
• 化学式: C₇H₆IN₃O
• 分子量: 275.049
• InChiKey: OKOZDIAJNQOGKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 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：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-azido-5-iodobenzyl alcohol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到(3-azido-5-iodo)benzyl bromide
  参考文献：
  名称：

  [125I]-N-[(3-Azido-5-iodo)benzyl]dantrolene and [125I]-N-{[3-Iodo-5-(3-trifluoromethyl-3H-diazirin-3-yl)]benzyl}dantrolene: photoaffinity probes specific for the physiological Ca2+ release from sarcoplasmic reticulum of skeletal muscle

  摘要：

  In order to capture and identify key molecules that regulate the release of Ca2+ from the sarcoplasmic reticulum (SR) of skeletal muscle, we designed specific photoaffinity probes based on the structural modification of dantrolene. Thus, GIF-0082 and GIF-0276 possessing azido- and trifluoromethyldiazirinyl-benzyl groups, respectively, at the hydantoin moiety were found to have a highly selective inhibitory effect on physiological Ca2+ release (PCR) without affecting Ca2+-induced Ca2+ release (CICR). Successful realization of the sharp discrimination between PCR and CICR has led to the creation of [I-125]GIF-0082 and [I-125]GIF-0276, which were synthesized by substituting a stannyl group with I-125 in the corresponding phenylstannane precursors. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00701-1
• 作为产物：
  描述：

  3-iodo-5-nitrobenzyl alcohol 在 盐酸 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 3-azido-5-iodobenzyl alcohol
  参考文献：
  名称：

  带有叠氮和末端炔基侧基的聚降冰片烯的合成

  摘要：

  摘要：开发了一种强大的方法来合成前所未有的聚降冰片烯，其带有带有叠氮化物和末端炔基的侧基。两个关键中间体，即3-叠氮基-5-（2-（三甲基甲硅烷基）乙炔基）苄醇和4-（4-氮杂-三环[5.2.1.0 2.6] dec-8-en-4-基）苯甲酸，最佳合成了相应单体的聚合合成。

  DOI：

  10.1016/j.cclet.2010.12.020

文献信息

• Formal C-H-Azidation - Based Shortcut to Diazido Building Blocks for the Versatile Preparation of Photoaffinity Labeling Probes
  作者：Suguru Yoshida、Yoshihiro Misawa、Takamitsu Hosoya

  DOI：10.1002/ejoc.201402516

  日期：2014.7

  synthetic routes to diazido building blocks with different connectable groups were established on the basis of the sequential iridium-catalyzed C–H borylation and copper-catalyzed azidation of 1,3-disubstituted benzenes, followed by diverse azido-friendly functional-group transformations. These building blocks facilitate the rapid development of effective diazido photoaffinity labeling probes that are useful

  在铱催化的 C-H 硼酸化和铜催化的 1,3-二取代苯的连续叠氮化反应的基础上，建立了具有不同可连接基团的二叠氮基单元的短合成路线，然后是多种叠氮基友好官能团转化。这些构建块促进了有效的二叠氮光亲和标记探针的快速开发，这些探针可用于识别生物活性化合物的未知目标生物分子。
• Facile synthesis of diazido-functionalized biaryl compounds as radioisotope-free photoaffinity probes by Suzuki–Miyaura coupling
  作者：Takamitsu Hosoya、Atsushi Inoue、Toshiyuki Hiramatsu、Hiroshi Aoyama、Takaaki Ikemoto、Masaaki Suzuki

  DOI：10.1016/j.bmc.2009.01.070

  日期：2009.3

  Suzuki–Miyaura coupling of 3-azido-5-(azidomethyl)phenylboronic acid pinacol ester with various aryl bromides affords corresponding diazido-functionalized biaryl compounds in good yields. This approach provides an easy access to radioisotope-free photoaffinity probes possessing biaryl structure. By using this method, we prepared a novel diazido-functionalized dantrolene analog, which showed selective

  将3-叠氮基-5-（叠氮基甲基）苯基硼酸频哪醇酯与各种芳基溴化物进行的Suzuki-Miyaura偶联，可以以良好的收率得到相应的二叠氮基官能化的联芳基化合物。这种方法可轻松访问具有联芳基结构的无放射性同位素的光亲和探针。通过使用这种方法，我们制备了一种新型的叠氮基官能化的双氢戊二烯类似物，其对小鼠骨骼肌肌浆网（SR）的生理性Ca 2+释放（PCR）具有选择性抑制作用，而不会影响Ca 2+诱导的Ca 2+释放（CICR）。
• Design of dantrolene-derived probes for radioisotope-free photoaffinity labeling of proteins involved in the physiological Ca2+ release from sarcoplasmic reticulum of skeletal muscle
  作者：Takamitsu Hosoya、Toshiyuki Hiramatsu、Takaaki Ikemoto、Hiroshi Aoyama、Tatsuro Ohmae、Makoto Endo、Masaaki Suzuki

  DOI：10.1016/j.bmcl.2005.01.041

  日期：2005.3

  Bifunctional dantrolene derivatives have been synthesized as probes for radioisotope-free photoaffinity labeling with the aim of elucidating the molecular mechanism of skeletal muscle contraction. GIF-0430 and GIF-0665 are aromatic azido-functionalized derivatives that were designed to selectively inhibit physiological Ca2+ release (PCR) from sarcoplasmic reticulum (SR) in mouse skeletal muscle without

  为了阐明骨骼肌收缩的分子机制，已经合成了双功能性的Dantrolene衍生物作为无放射性同位素光亲和标记的探针。GIF-0430和GIF-0665是芳香族叠氮基官能化衍生物，旨在选择性抑制小鼠骨骼肌肌浆网（SR）的生理性Ca2 +释放（PCR），而对Ca2 +诱导的Ca2 +释放（CICR）没有强烈影响。这些光亲和探针分别由叠氮基甲基或乙炔基组成，它们可以充当标签，用于在光交联操作后通过适当的化学选择性连接方法引入可选的可检测标记单元。实际上，
• Synthesis of Diverse 3-Azido-5-(azidomethyl)benzene Derivatives via Formal C–H Azidation and Functional Group-Selective Transformations
  作者：Takamitsu Hosoya、Suguru Yoshida、Yoshitake Nishiyama、Yoshihiro Misawa、Yuki Hazama、Kazuhiro Oya

  DOI：10.3987/com-18-s(f)72

  日期：——
• Synthesis of polynorbornene with pendant moiety bearing azide and terminal alkyne groups
  作者：Ze Zhang、Zhi Wei Peng、Kun Zeng Fan

  DOI：10.1016/j.cclet.2010.12.020

  日期：2011.7

  Abstract A powerful approach to the synthesis of an unprecedented polynorbornene with pendant moiety bearing azide and terminal alkyne groups is developed. Two key intermediates, namely, 3-azido-5-(2-(trimethylsilyl)ethynyl) benzyl alcohol and 4-(4-aza-tricyclo [5.2.1.0 2.6 ]dec-8-en-4-yl) benzoic acid, were optimally synthesized for convergent synthesis of the corresponding monomer.

  摘要：开发了一种强大的方法来合成前所未有的聚降冰片烯，其带有带有叠氮化物和末端炔基的侧基。两个关键中间体，即3-叠氮基-5-（2-（三甲基甲硅烷基）乙炔基）苄醇和4-（4-氮杂-三环[5.2.1.0 2.6] dec-8-en-4-基）苯甲酸，最佳合成了相应单体的聚合合成。