octan-2-yl N,N'-di(propan-2-yl)carbamimidate | 113984-36-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: octan-2-yl N,N'-di(propan-2-yl)carbamimidate
• CAS: 113984-36-4
• 化学式: C₁₅H₃₂N₂O
• 分子量: 256.432
• InChiKey: IOGILBWOIQGYIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  368.3±11.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  正癸酸 、 octan-2-yl N,N'-di(propan-2-yl)carbamimidate 以 乙腈 为溶剂， 反应 0.08h， 以60%的产率得到2-octyl decanoate
  参考文献：
  名称：

  Microwave-Assisted Ester Formation Using O-Alkylisoureas: A Convenient Method for the Synthesis of Esters with Inversion of Configuration

  摘要：

  The formation of carboxylic esters via reaction of carboxylic acids with O-alkylisoureas proceeds in excellent yields with very short reaction times when conducted in a monomode microwave synthesizer. Efficient processes were developed using preformed or commercially available isoureas derived from primary and secondary alcohols, with a reaction time of only 5 min or less. It was demonstrated that under these microwave conditions, ester formation proceeded in good yields with clean inversion of configuration where appropriate. The process was validated using menthol, a hindered substrate for S(N)2 reactions. In addition, starting from primary alcohols, ester formation was successfully accomplished using ail in situ isourea formation procedure. A polymer-assisted solution-phase procedure was also developed by employing preformed solid-supported isoureas and by an efficient "catch and release" ester formation procedure whereby primary alcohols were caught on resin as isoureas by reaction with immobilized carbodiimide and released as esters by subsequent treatment with a carboxylic acids.

  DOI：

  10.1021/jo900476y
• 作为产物：
  描述：

  仲辛醇 、 N,N'-二异丙基碳二亚胺 在 copper(l) chloride 作用下， 反应 60.0h， 以70%的产率得到octan-2-yl N,N'-di(propan-2-yl)carbamimidate
  参考文献：
  名称：

  经由O-烷基异脲将醇转化为烷基溴化物和碘化物

  摘要：

  用三氟甲磺酸和四丁基铵盐（溴化物或碘化物）处理O-烷基异脲，可高产率地得到烷基卤化物。

  DOI：

  10.1016/s0040-4039(00)96534-1

文献信息

• A Novel Synthesis of 2-Alkylthiobenzothiazoles and 2-Alkylthiobenzoxazoles
  作者：Yanfei Yu、Zhengning Li、Lan Jiang

  DOI：10.1080/10426507.2011.636229

  日期：2012.5

  3H-Benzothiazole-2-thione and 3H-benzoxazole-2-thione were selectively S-alkylated by use of O-alkylisoureas as the alkylating reagents. The reactions could be performed under mild reaction conditions in short reaction times, and high yields were obtained using O-primary-alkylisoureas, whereas low yields were obtained with sec- and tert-alkylisoureas.
• COLLINGWOOD, STEPHEN P.;DAVIES, ALAN P.;GOLDING, BERNARD T., TETRAHEDRON LETT., 28,(1987) N 38, 4445-4448
  作者：COLLINGWOOD, STEPHEN P.、DAVIES, ALAN P.、GOLDING, BERNARD T.

  DOI：——

  日期：——
• Microwave-Assisted Ester Formation Using <i>O</i>-Alkylisoureas: A Convenient Method for the Synthesis of Esters with Inversion of Configuration
  作者：Alessandra Chighine、Stefano Crosignani、Marie-Claire Arnal、Mark Bradley、Bruno Linclau

  DOI：10.1021/jo900476y

  日期：2009.7.3

  The formation of carboxylic esters via reaction of carboxylic acids with O-alkylisoureas proceeds in excellent yields with very short reaction times when conducted in a monomode microwave synthesizer. Efficient processes were developed using preformed or commercially available isoureas derived from primary and secondary alcohols, with a reaction time of only 5 min or less. It was demonstrated that under these microwave conditions, ester formation proceeded in good yields with clean inversion of configuration where appropriate. The process was validated using menthol, a hindered substrate for S(N)2 reactions. In addition, starting from primary alcohols, ester formation was successfully accomplished using ail in situ isourea formation procedure. A polymer-assisted solution-phase procedure was also developed by employing preformed solid-supported isoureas and by an efficient "catch and release" ester formation procedure whereby primary alcohols were caught on resin as isoureas by reaction with immobilized carbodiimide and released as esters by subsequent treatment with a carboxylic acids.
• Conversion of alcohols into alkyl bromides and iodides via O-alkylisoureas
  作者：Stephen P. Collingwood、Alan P. Davies、Bernard T. Golding

  DOI：10.1016/s0040-4039(00)96534-1

  日期：1987.1

  Treatment of O-alkylisoureas with trifluoromethanesulphonic acid and a tetrabutylammonium salt (bromide or iodide) affords alkyl halides in high yields.

  用三氟甲磺酸和四丁基铵盐（溴化物或碘化物）处理O-烷基异脲，可高产率地得到烷基卤化物。