10-azido-1,2-epoxy decane | 292601-61-7

• 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: 10-azido-1,2-epoxy decane
• 英文别名: 1-Azido-9,10-epoxydecane；2-(8-Azidooctyl)oxirane；2-(8-azidooctyl)oxirane
• CAS: 292601-61-7
• 化学式: C₁₀H₁₉N₃O
• 分子量: 197.28
• InChiKey: HFQYTBDZOXLEGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  9
• 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：

  10-azido-1,2-epoxy decane 在 5percent Pd/C(en) 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以97%的产率得到1-Amino-9,10-epoxydecane
  参考文献：
  名称：

  Highly Chemoselective Hydrogenation with Retention of the Epoxide Function Using a Heterogeneous Pd/C-Ethylenediamine Catalyst and THF

  摘要：

  In general, palladium-carbon (Pd/C) catalyzed hydrogenation of epoxides affords the corresponding primary and secondary alcohols as a mixture. It has been found that the catalytic activity of a Pd/C -ethylenediamine complex catalyst [Pd/C(en)] in the hydrogenolysis of epoxide functions is drastically reduced. Herein we describe a mild and chemoselective method for the hydrogenation of olefin, nitro, and azide functions with retention of the epoxide function. The chemoselectivity was accomplished by using a combination of 5% Pd/C(en) and THF as solvent. A significant drop in the chemoselectivity of the hydrogenation is observed with 5% Pd/C(en) in MeOH. These results reinforce the utility of epoxides as important precursors of alcohols in synthetic chemistry.

  DOI：

  10.1002/1521-3765(20000616)6:12<2200::aid-chem2200>3.0.co;2-3
• 作为产物：
  描述：

  dec-9-en-1-yl methanesulfonate 在 sodium azide 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 10-azido-1,2-epoxy decane
  参考文献：
  名称：

  Highly Chemoselective Hydrogenation with Retention of the Epoxide Function Using a Heterogeneous Pd/C-Ethylenediamine Catalyst and THF

  摘要：

  In general, palladium-carbon (Pd/C) catalyzed hydrogenation of epoxides affords the corresponding primary and secondary alcohols as a mixture. It has been found that the catalytic activity of a Pd/C -ethylenediamine complex catalyst [Pd/C(en)] in the hydrogenolysis of epoxide functions is drastically reduced. Herein we describe a mild and chemoselective method for the hydrogenation of olefin, nitro, and azide functions with retention of the epoxide function. The chemoselectivity was accomplished by using a combination of 5% Pd/C(en) and THF as solvent. A significant drop in the chemoselectivity of the hydrogenation is observed with 5% Pd/C(en) in MeOH. These results reinforce the utility of epoxides as important precursors of alcohols in synthetic chemistry.

  DOI：

  10.1002/1521-3765(20000616)6:12<2200::aid-chem2200>3.0.co;2-3

文献信息

• Oxidation of Azides by the HOF·CH₃CN:  A Novel Synthesis of Nitro Compounds
  作者：Mira Carmeli、Shlomo Rozen

  DOI：10.1021/jo060440u

  日期：2006.6.1

  aromatic rings, ketones, nitriles, halides, alcohols, and esters are tolerated. Sulfides react with HOF·CH3CN usually at the same rate as azides. Amines and olefins, however, react faster, so they have to be protected first. Nitro derivatives with various oxygen isotopes can be made using the labeled H18OF·CH3CN. In the case of chiral azides the stereochemistry around the nitrogen-bonded carbons is retained

  通过使F 2通过乙腈水溶液可轻松制备HOF·CH 3 CN络合物，它是一种非常有效的氧转移剂。其将各种叠氮化物氧化成相应的硝基衍生物的能力是独特的。该方法需要短的反应时间和室温或更低的温度，并且通常以非常高的收率分离出所需的硝基化合物。据信各自的亚硝基衍生物是该反应的中间体。可以容忍芳香环，酮，腈，卤化物，醇和酯等官能团。硫化物与HOF·CH 3反应CN通常与叠氮化物的速率相同。但是，胺和烯烃的反应速度更快，因此必须首先对其进行保护。使用标记的H 18 OF·CH 3 CN可以制备具有各种氧同位素的硝基衍生物。在手性叠氮化物的情况下，保留了氮键合碳周围的立体化学。
• Highly Chemoselective Hydrogenation with Retention of the Epoxide Function Using a Heterogeneous Pd/C-Ethylenediamine Catalyst and THF
  作者：Hironao Sajiki、Kazuyuki Hattori、Kosaku Hirota

  DOI：10.1002/1521-3765(20000616)6:12<2200::aid-chem2200>3.0.co;2-3

  日期：2000.6.16

  In general, palladium-carbon (Pd/C) catalyzed hydrogenation of epoxides affords the corresponding primary and secondary alcohols as a mixture. It has been found that the catalytic activity of a Pd/C -ethylenediamine complex catalyst [Pd/C(en)] in the hydrogenolysis of epoxide functions is drastically reduced. Herein we describe a mild and chemoselective method for the hydrogenation of olefin, nitro, and azide functions with retention of the epoxide function. The chemoselectivity was accomplished by using a combination of 5% Pd/C(en) and THF as solvent. A significant drop in the chemoselectivity of the hydrogenation is observed with 5% Pd/C(en) in MeOH. These results reinforce the utility of epoxides as important precursors of alcohols in synthetic chemistry.