glycidyl azide | 80044-09-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: glycidyl azide
• 英文别名: 1-azido-2,3-epoxypropane；azidomethyloxirane；2-(azidomethyl)oxirane
• CAS: 80044-09-3
• 化学式: C₃H₅N₃O
• 分子量: 99.0922
• InChiKey: JSOGDEOQBIUNTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  glycidyl azide 在 sodium azide 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 5.0h， 生成 1,3-diazido 2-propanol
  参考文献：
  名称：

  Enzymatic dynamic kinetic resolution of epihalohydrins

  摘要：

  The haloalcohol dehalogenase from Agrobacterium radiobacter AD1 catalyses the reversible ring closure of vicinal haloalcohols to produce epoxides and halides. In the ring opening of epoxides, nonhalide nucleophiles such as N-3(-) are accepted. The enantioselective irreversible ring opening of an epihalohydrin by N-3(-), combined with racemisation caused by a reversible ring opening by a halide, resulted in an enzymatic dynamic kinetic resolution yielding optically active (S)-1-azido-3-halo-2-propanol. With epichlorohydrin as a substrate, the rate of ring opening by N-3(-) was higher than the rate of racemisation, resulting in a mixed kinetic resolution and dynamic kinetic resolution. With epibromohydrin as the substrate, the racemisation rate was higher than the rate of ring opening, resulting in an efficient dynamic kinetic resolution. By optimising the pH of the medium and the concentrations of N-3(-) and Br-, the product (S)-1-azido-3-bromo-2-propanol could be obtained in 84% yield and 94% ee. An (R)-enantiomer selective ring closure of this bromoalcohol, catalysed by the same enzyme, caused a simultaneously occurring kinetic resolution, yielding when the conversion progressed, an increase in enantiopurity of (S)-1-azido-3-bromo-2-propanol to >99% ee with a yield of 77%. This compound and the ring-closed product glycidyl azide can be used as chiral synthetic building blocks. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.009
• 作为产物：
  描述：

  环氧氯丙烷 在 sodium azide 作用下， 以 水 为溶剂， 生成 glycidyl azide
  参考文献：
  名称：

  Synthesis of N-(3-Azido-2-hydroxypropyl), N-(3-Phthalimido-2-hydroxypropyl) and N-(3-Amino-2-hydroxypropyl) Derivatives of Heterocyclic Bases

  摘要：

  杂环碱与氮甲基环氧丙烷（I）在钾或铯碳酸盐的碱性催化下发生烷基化反应，形成N-(3-叠氮-2-羟基丙基)衍生物II。将这些化合物在钯碳上进行氢化反应，得到相应的3-氨基-2-羟基丙基衍生物III。同样的化合物III可通过在铯碳酸盐存在下，将杂环碱与邻苯二甲酰亚氨基环氧丙烷（VII）发生烷基化反应，并将形成的N-(3-邻苯二甲酰亚氨基-2-羟基丙基)衍生物VIII与联氨反应制备。邻苯二甲酰亚氨基衍生物VIII在弱碱性水介质中易于水解，形成9-[3-(邻二甲酰苯胺基)-2-羟基丙基]衍生物IX和X。

  DOI：

  10.1135/cccc19941153

文献信息

• Interrupted CuAAC‐Thiolation for the Construction of 1,2,3‐Triazole‐Fused Eight‐Membered Heterocycles from <i>O</i> ‐/ <i>N</i> ‐Propargyl derived Benzyl Thiosulfonates with Organic Azides
  作者：Raju Jannapu Reddy、Md. Waheed、Arram Haritha Kumari、Gamidi Rama Krishna

  DOI：10.1002/adsc.202101256

  日期：2022.1.18

  click-sulfenylation of O-/N-propargyl benzyl thiosulfonates with organic azides has been disclosed. The unified CuAAC-thiolation provides a wide range of triazole-fused eight-membered heterocycles in good to high (51–94%) yields under mild reaction conditions. Moreover, a three-component reaction is also achieved involving O-/N-propargyl benzyl thiosulfonates, benzyl bromide, and sodium azide to deliver fused-triazoles

  已公开了铜 (I) 催化的O-/N-炔丙基苄基硫代磺酸盐与有机叠氮化物的间断点击亚磺酰化。在温和的反应条件下，统一的 CuAAC-硫醇化提供了范围广泛的三唑稠合八元杂环，产率从好到高（51-94%）。此外，还实现了涉及O-/N-炔丙基苄基硫代磺酸盐、苄基溴和叠氮化钠的三组分反应，以 61-74% 的收率提供稠合三唑。从合成的角度来看，本协议已在克级反应中得到证明。基于实验结果和对照实验，还提出了一种似是而非的机制。
• [EN] FLUORESCENT BISPHOSPHONATE ANALOGS<br/>[FR] ANALOGUES DE BISPHOSPHONATES FLUORESCENTS
  申请人：UNIV SOUTHERN CALIFORNIA

  公开号：WO2016161407A1

  公开（公告）日：2016-10-06

  Fluorescent probes based on N-heterocyclic bisphosphonates or their phosphonocarboxylate analogues are provided. The probes have variable spectroscopic properties, bone mineral binding affinities, and pharmacological activities. Methods for preparing the probes include the use of two complementary linking strategies, one involving an amino group and the other involving a chloride group as a precursor to an amino group. In other versions, bifunctional N-heterocyclic bisphosphonates are provided having an amino group and an azido group as linking moieties. In some versions, the linking chemistry allows attachment of a wide selection of fluorescent dyes in the visible to near-infrared range to any of three clinically important heterocyclic bisphosphonates.

  基于N-杂环双膦酸盐或其膦酸盐类似物的荧光探针已提供。这些探针具有可变的光谱特性、骨矿物结合亲和力和药理活性。制备这些探针的方法包括使用两种互补的连接策略，一种涉及氨基团，另一种涉及氯化物作为氨基团的前体。在其他版本中，提供了具有氨基团和偶氮基团作为连接基团的双功能N-杂环双膦酸盐。在某些版本中，连接化学允许将广泛选择的荧光染料附着在可见光到近红外范围内的三种临床重要的杂环双膦酸盐中的任何一种上。
• Synthese eines Azaanalogen des Antibiotikums Negamycin
  作者：Wolfgang Streicher、Hellmuth Reinshagen

  DOI：10.1002/cber.19751080314

  日期：1975.3

  Die Synthese des 3-Azaanalogen (2) des Antibiotikums Negamycin wird mitgeteilt. Das neue Derivat besitzt keine antibakterielle Aktivität.

  据报道，抗生素尼古霉素的3-氮杂类似物（2）的合成。新衍生物没有抗菌活性。
• Copper(I) Acetate: A Structurally Simple but Highly Efficient Dinuclear Catalyst for Copper-Catalyzed Azide-Alkyne Cycloaddition
  作者：Changwei Shao、Guolin Cheng、Deyong Su、Jimin Xu、Xinyan Wang、Yuefei Hu

  DOI：10.1002/adsc.200900768

  日期：——

  this article, the structurally well‐defined dinuclear complex copper(I) acetate was studied in detail and was developed as a highly practical and efficient catalyst for the copper(I)‐catalyzed azide‐alkyne cycloaddition. The “bare” phenylethynylcopper(I) (i.e., with no exogeneous ligands) was isolated as an intermediate, which can be converted into an active catalytic species by treatment with acetic

  在本文中，对结构明确的双核络合乙酸铜（I）进行了详细研究，并将其开发为铜（I）催化的叠氮化物-炔烃环加成反应的一种高度实用且高效的催化剂。分离出“裸露的”苯基乙炔基铜（I）（即没有外源性配体）作为中间体，可以通过用乙酸处理（反应中原位产生）以有效催化叠氮化物的方式将其转化为活性催化物质。炔烃在温和条件下的环加成反应。
• Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 2. The "A" group
  作者：Walter A. Gregory、David R. Brittelli、C. L. J. Wang、Hollis S. Kezar、Randall K. Carlson、Chung Ho Park、Peter F. Corless、Steven J. Miller、P. Rajagopalan

  DOI：10.1021/jm00171a035

  日期：1990.9

  Chem. 1989, 32, 1673) or by elaboration of the synthetic intermediate 2 (A = H) via electrophilic aromatic substitution or elaboration of the intermediate 2 (A = I) by transition metal catalyzed carbon-carbon bond-forming reactions. Antibacterial evaluation of compounds 2 with A = alkyl, ethenyl, ethynyl, hydroxyalkyl, aldo and keto, oximinoakyl, carboalkoxy, nitro, amino, halo and psi-halo, alkylthio

  描述了一系列5-（乙酰氨基甲基）恶唑烷酮抗菌药（2）中改变“ A”基团的作用的合成和构效关系（SAR）研究。化合物2主要通过前述的六步合成法（J. Med。Chem。1989，32，1673）或通过亲电子芳族取代合成中间体2（A = H）或中间体2制备而制备。 （A ＝ I）通过过渡金属催化的碳-碳键形成反应。化合物2的A =烷基，乙烯基，乙炔基，羟烷基，醛基和酮基，氧亚氨基烷基，碳烷氧基，硝基，氨基，卤素和psi-卤代，烷硫基，烷基亚磺酰基和烷基磺酰基的抗菌评估，导致金黄色葡萄球菌和粪肠球菌的鉴定SAR趋势。在几个系列的同系物（烷基，酮基，轴氨基烷基，氨基，卤素和psi-卤代和烷硫基）中，抗菌活性随亲脂性的增加而增加。但是在A是一个三或四取代（大于H的取代基）季原子直接连接于芳环（羟烷基，烷基亚磺酰基，烷基磺酰基）的取代基上，其活性在具有“叔丁基”的系列成员处达到峰值连接模式。相对于具有