2-azido-2-(4-(fluoro)phenyl)ethanol | 866886-40-0

• 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-azido-2-(4-(fluoro)phenyl)ethanol
• 英文别名: 2-Azido-2-(4-fluorophenyl)ethan-1-ol；2-azido-2-(4-fluorophenyl)ethanol
• CAS: 866886-40-0
• 化学式: C₈H₈FN₃O
• 分子量: 181.169
• InChiKey: JEYRHSNZRUFMOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-azido-2-(4-(fluoro)phenyl)ethanol 在 palladium on activated charcoal 作用下， 以 甲醇 为溶剂， 生成 2-氨基-2-(4-氟苯基)乙醇
  参考文献：
  名称：

  Novel diarylsulfonylurea derivatives as potent antimitotic agents

  摘要：

  A novel series of diarylsulfonylurea derivatives were synthesized and evaluated for interaction with tubulin and for cytotoxicity against human cancer cell lines. These derivatives demonstrated good inhibitory activity against tubulin polymerization, which was well correlated with promising antiproliferative activity as well as G2/M phase cell cycle arrest. Furthermore, several compounds were also efficacious against multidrug-resistant cancer cells, which are resistant to many other known microtubule inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.069
• 作为产物：
  描述：

  (±)-4-氟苯乙烯环氧化物 在 sodium azide 、 halohydrin dehalogenase from Ilumatobacter coccineus 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 为溶剂， 反应 12.0h， 以80%的产率得到2-azido-2-(4-(fluoro)phenyl)ethanol
  参考文献：
  名称：

  球孢菌卤代醇脱卤酶催化环氧化物的高 α 位区域选择性开环：2-azido-2-aryl-1-ols 的生物催化方法†

  摘要：

  卤代醇脱卤酶通常被认为是亲核试剂介导的环氧化物开环中严格的 β 位区域选择性酶。在这里，我们发现来自Ilumatobacter coccineus的 HheG 在叠氮介导的氧化苯乙烯衍生物1a-1k的开环中表现出优异的 α 位区域选择性，产生相应的 2-azido-2-aryl-1-ols 2a-2k，产率高达 96%。

  DOI：

  10.1039/c9ra03774h

文献信息

• Some New Aspects of the Boyer Reaction
  作者：Rupak Chakraborty、Veronica Franz、Ghanashyam Bez、Dipali Vasadia、Chenchu Popuri、Cong-Gui Zhao

  DOI：10.1021/ol051442o

  日期：2005.9.1

  [reaction: see text] The reaction outcome of 2-azidoethanol and aliphatic aldehyde is found to be dependent on the catalyst and the structure of the azido alcohol. Under the catalysis of Cu(II) triflate, the corresponding acetal is obtained. A similar reaction between 2-aryl-2-azidoethanol and aldehyde catalyzed by BF3 yields a mixture of 3-oxazoline and 2-oxazoline. The latter reaction has been used

  [反应：见正文]发现2-叠氮基乙醇与脂肪醛的反应结果取决于叠氮基醇的催化剂和结构。在三氟甲磺酸铜（II）的催化下，获得了相应的缩醛。由BF 3催化的2-芳基-2-叠氮基乙醇与醛之间的类似反应产生了3-恶唑啉和2-恶唑啉的混合物。后一反应已用于制备具有良好对映选择性的3-恶唑啉。
• Iron‐Catalysed Remote C(sp ³ )−H Azidation of <i>O</i> ‐Acyl Oximes and <i>N</i> ‐Acyloxy Imidates Enabled by 1,5‐Hydrogen Atom Transfer of Iminyl and Imidate Radicals: Synthesis of γ‐Azido Ketones and β‐Azido Alcohols
  作者：Rubén O. Torres‐Ochoa、Alexandre Leclair、Qian Wang、Jieping Zhu

  DOI：10.1002/chem.201901079

  日期：2019.7.17

  acetylacetonate [Fe(acac)3], the reaction of structurally diverse ketoxime esters with trimethylsilyl azide (TMSN3) afforded γ‐azido ketones in good to excellent yields. This unprecedented distal γ‐C(sp3)−H bond azidation reaction went through a sequence of reductive generation of an iminyl radical, 1,5‐hydrogen atom transfer (1,5‐HAT) and iron‐mediated redox azido transfer to the translocated carbon radical

  在催化量的乙酰丙酮铁（III）[Fe（acac）3 ]的存在下，结构多样的酮肟酸酯与三甲基硅烷基叠氮化物（TMSN 3）的反应可提供良好产率的γ-叠氮基酮。前所未有的远端γ-C（sp 3）-H键叠氮化反应经历了亚胺基的还原生成，1,5-氢原子转移（1,5-HAT）以及铁介导的氧化还原叠氮基转移至易位的碳自由基。TMSN 3不仅用作功能化未激活的C（sp 3）-H键的氮源，而且还用作还原剂以原位生成催化活性的Fe II。基于相同的原理，一种新颖的β-C（sp3）-H通过N-酰氧基酰亚胺的醇官能化随后被实现，在将所得的酯水解后，导致β-叠氮基醇，这是有机和药物化学的重要组成部分。
• Halohydrin dehalogenase-catalysed synthesis of fluorinated aromatic chiral building blocks
  作者：Irena Dokli、Nevena Milčić、Petra Marin、Marina Svetec Miklenić、Martina Sudar、Lixia Tang、Zvjezdana Findrik Blažević、Maja Majerić Elenkov

  DOI：10.1016/j.catcom.2021.106285

  日期：2021.4

  Kinetic resolution of a series of fluorinated styrene oxide derivatives was studied using halohydrin dehalogenase. A mutant HheC-W249P catalysed nucleophilic ring-opening with azide and cyanide ions with excellent enantioselectivity (E-values up to >200), which gives access to various enantiopure β-substituted alcohols and epoxides. It was found that the enzyme tolerates substrates in concentrations

  使用卤代醇脱卤酶研究了一系列氟化苯乙烯氧化物的动力学拆分。突变体HheC-W249P用叠氮化物和氰化物离子催化的亲核开环，具有出色的对映选择性（E值高达> 200），可用于各种对映纯的β-取代的醇和环氧化物。发现该酶以超过50mM的浓度耐受底物。然而，在升高的浓度和延长的反应时间下观察到不同的副反应。外消旋的4-三氟甲基苯乙烯氧化物的生物催化叠氮和氰基水解反应按制备规模进行，得到（R）-2-叠氮基-1-（4-三氟甲基-苯基）-乙醇，产率为38％，ee为97％，而（S）-3-羟基-3-（4-三氟甲基-苯基）-丙腈，产率为30％，ee为98％。
• Biocatalytic approach to chiral fluoroaromatic scaffolds
  作者：Irena Dokli、Zlatko Brkljača、Petra Švaco、Lixia Tang、Višnja Stepanić、Maja Majerić Elenkov

  DOI：10.1039/d2ob01955h

  日期：——

  Ten different fluorinated aromatic epoxides have been tested as potential substrates for halohydrin dehalogenase (HHDH) HheC. The majority of investigated epoxides are useful building blocks in synthetic chemistry applications, with a number of them being polysubstituted. Moderate to high enantioselectivities (ER = 15 → 200) were observed in azidolysis, allowing the synthesis of enantioenriched (R)-azido

  已经测试了十种不同的氟化芳族环氧化物作为卤代醇脱卤酶 (HHDH) HheC 的潜在底物。大多数研究的环氧化物是合成化学应用中有用的结构单元，其中许多是多取代的。在叠氮解中观察到中等到高对映选择性 ( ER = 15 → 200)，从而允许合成分子中含有氟的对映体富集 (R ) -叠氮醇。如果反应的转化率超过 50%，也可以使用对映体纯 ( S )-环氧化物。虽然o -F-氧化苯乙烯很容易转化为产物，但空间上具有挑战性的o -CF 3-导数不被 HheC 接受。结合位点的计算机探测表明，为了在 HheC 活性位点中容纳o -CF 3 - 衍生物，有必要消除空间位阻。因此，我们通过探测几个在活性位点中包含相关修饰的可用 HheC 变体来扩展我们的研究。鉴定出活性突变体 P84V/F86P/T134A/N176A（命名为 HheC-M4），不仅对o -CF 3 -氧化苯乙烯具有高活性，而且还具有反向对映选择性
• Novel diarylsulfonylurea derivatives as potent antimitotic agents
  作者：Semi Kim、Ji Hyun Park、Sun-Young Koo、Jung In Kim、Min-Hyeung Kim、Ji Eun Kim、Kiwon Jo、Hwan Geun Choi、Sung Bae Lee、Sang-Hun Jung

  DOI：10.1016/j.bmcl.2004.09.069

  日期：2004.12

  A novel series of diarylsulfonylurea derivatives were synthesized and evaluated for interaction with tubulin and for cytotoxicity against human cancer cell lines. These derivatives demonstrated good inhibitory activity against tubulin polymerization, which was well correlated with promising antiproliferative activity as well as G2/M phase cell cycle arrest. Furthermore, several compounds were also efficacious against multidrug-resistant cancer cells, which are resistant to many other known microtubule inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.