Methyl trans-2-azido-1-hydroxycyclohexanecarboxylate | 1932519-59-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl trans-2-azido-1-hydroxycyclohexanecarboxylate
• 英文别名: Cyclohexanecarboxylic acid, 2-azido-1-hydroxy-, methyl ester, (1R,2R)-；methyl (1R,2R)-2-azido-1-hydroxycyclohexane-1-carboxylate
• CAS: 1932519-59-9
• 化学式: C₈H₁₃N₃O₃
• 分子量: 199.21
• InChiKey: XYTTUFMOTNELFH-HTRCEHHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl trans-2-azido-1-hydroxycyclohexanecarboxylate 在 sodium tetrahydroborate 、 十六烷基三甲基溴化铵 、 cobalt(II) chloride 作用下， 以 水 为溶剂， 反应 0.17h， 以95%的产率得到Methyl trans-2-amino-1-hydroxy-cyclohexanecarboxylate
  参考文献：
  名称：

  氯化钴(II)催化化学选择性硼氢化钠还原水中叠氮化物

  摘要：

  将叠氮化物还原为胺和酰胺是在催化非均相条件下使用 NaBH4/CoCl2·6 H2O 在 25 °C 的单一水中进行的。广谱叠氮化物在短时间内被还原，化学选择性高产率和纯度。

  DOI：

  10.1055/s-2000-6389
• 作为产物：
  描述：

  环己烯甲酸 在 Oxone 、 三氯化铝 、 sodium azide 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 生成 Methyl trans-2-azido-1-hydroxycyclohexanecarboxylate
  参考文献：
  名称：

  Efficient O-Trimethylsilylation of Alcohols and Phenols with Trimethylsilyl Azide Catalyzed by Tetrabutylammonium Bromide under Neat Conditions

  摘要：

  A very efficient procedure for the trimethylsilylation of a wide variety of alcohols, including primary, allylic, benzylic, secondary, hindered secondary, tertiary, and phenols is reported. The reactions were carried out under neat conditions with trimethylsilyl azide (TMSN3) and, when necessary, in the presence of a catalytic amount (20 mol %) of tetrabutylammonium bromide (TBABr) at 30 or 70 degreesC. Under catalytic conditions, the yields of the corresponding trimethylsilyl ethers were greater than 91%. This procedure also allows the selective protection of primary and secondary alcohols in the presence of tertiary ones.

  DOI：

  10.1021/jo015814s

文献信息

• A convenient synthesis of aziridine-2-carboxylic esters
  作者：Johan Legters、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1002/recl.19921110101

  日期：——

  Optically active oxirane-2-carboxylic esters, prepared from allylic alcohols employing the Sharpless epoxidation, were treated with sodium azide. The azido alcohols obtained were subsequently converted into aziridine-2-carboxylic esters by reaction with triphenylphosphine, in good yields and with high optical purity. Various racemic oxirane-2-carboxylic esters were subjected to the same sequence of

  用叠氮化钠处理由使用Sharpless环氧化的烯丙基醇制备的旋光环氧乙烷-2-羧酸酯。随后通过与三苯基膦反应以高收率和高光学纯度将获得的叠氮基醇转化为氮丙啶-2-羧酸酯。使各种外消旋环氧乙烷-2-羧酸酯进行相同的反应顺序。
• Azidolysis of α,β-Epoxycarboxylic Acids. A Water-Promoted Process Efficiently Catalyzed by Indium Trichloride at pH 4.0
  作者：Francesco Fringuelli、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1021/jo015564f

  日期：2001.5.1

  The catalytic efficiency of InCl3, Yb(OTf)(3), and Sc(OTf)(3) in the azidolysis of alpha,beta -epoxycarboxylic acids has been studied in water and in organic solvents, for comparison using NaN3 and Me3SiN3 as the source of the azido group. In water, the catalytic effectiveness of these metal salts strongly depends on the pH of the aqueous medium and on the type of Lewis acid catalyst. In water their catalytic activity is mostly due to the corresponding aqua ion species, the concentration of which becomes significant when the pH of the aqueous medium is below the corresponding pK(1,1) hydrolysis constant. The process is more efficient in water than in organic solvents. At pH 4.0, InCl3 is a far better catalyst than Yb(OTf)(3) or Sc(OTf)(3) and allows the highly regio- and diasteroselective preparation of beta -azido-alpha -hydroxycarboxylic acids, which can be isolated in pure form in very high yields.