N,N'-diisopropyl-O-allylisourea | 3116-52-7

• 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: N,N'-diisopropyl-O-allylisourea
• 英文别名: O-allyl-N,N'-diisopropylisourea；O-allyldiisopropylisourea；O-Allyl-N.N'-diisopropyl-isoharnstoff；prop-2-enyl N,N'-di(propan-2-yl)carbamimidate
• CAS: 3116-52-7
• 化学式: C₁₀H₂₀N₂O
• 分子量: 184.282
• InChiKey: VACKRIGOKMQYJN-UHFFFAOYSA-N

物化性质

• 沸点：
  75-76 °C(Press: 10 Torr)
• 密度：
  0.8829 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  3-(3,4-methylenedioxyphenyl)-2-hydroxypropanoic acid 、 N,N'-diisopropyl-O-allylisourea 以 四氢呋喃 为溶剂， 反应 48.0h， 以94%的产率得到Prop-2-enyl 3-(1,3-benzodioxol-5-yl)-2-hydroxypropanoate
  参考文献：
  名称：

  Bryophyte Constituents; 7: New Synthesis of (+)-Rosmarinic Acid and Related Compounds

  摘要：

  描述了迷迭香酸（1）及其衍生物2-4的高效快捷合成方法，广泛采用了烯丙基保护基团用于羧酸和酚类构建单元。通过化学酶促拆分其苯基乳酸前体，获得了(+)-(R)-迷迭香酸。

  DOI：

  10.1055/s-1996-4289
• 作为产物：
  描述：

  烯丙醇 、 N,N'-二异丙基碳二亚胺 在 copper dichloride 作用下， 生成 N,N'-diisopropyl-O-allylisourea
  参考文献：
  名称：

  Schmidt,E. et al., Justus Liebigs Annalen der Chemie, 1965, vol. 685, p. 161 - 166

  摘要：

  DOI：

文献信息

• Conformational Study and Enantioselective, Regiospecific Syntheses of Novel Aminoxy <i>trans</i>-Proline Analogues Derived from an Acylnitroso Diels−Alder Cycloaddition
  作者：Brock T. Shireman、Marvin J. Miller、Marco Jonas、Olaf Wiest

  DOI：10.1021/jo010284l

  日期：2001.9.1

  temperature 1H NMR studies. The syntheses of the acylnitroso-derived peptides utilized two methods to selectively functionalize either of two chemically similar esters in the acylnitroso-derived amino acids. A novel transpeptidation of the amino acid that controlled the absolute stereochemistry in the acylnitroso Diels-Alder cycloaddition took advantage of an activated aminoxy amide linkage to control

  脯氨酸酰胺键的顺式/反式异构化在生物学过程中具有许多含义。代表性的衍生自环戊二烯的酰基亚硝基衍生的脯氨酸类似物的构象仅在CD2Cl2中以E或反式构象存在。除低温1H NMR研究外，在理论上B3LYP / 6-31G的水平上，使用COSMO自洽反应场计算确定了在能量上有利的构象。酰基亚硝基衍生的肽的合成利用两种方法选择性地官能化酰基亚硝基衍生的氨基酸中的两种化学相似的酯中的任一种。控制酰基亚硝基Diels-Alder环加成反应中绝对立体化学的氨基酸的新型转肽利用了活化的氨氧基酰胺键来控制区域化学。或者，外消旋二甲基酯的对映选择性和区域特异性酶促拆分提供了新的氨氧基酸。
• 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.
• 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.
• Synthesis and siderophore activity of albomycin-like peptides derived from N5-acetyl-N5-hydroxy-L-ornithine
  作者：E. Kurt Dolence、Chia En Lin、Marvin J. Miller、Shelley M. Payne

  DOI：10.1021/jm00107a013

  日期：1991.3

  N5-Acetyl-N5-hydroxy-L-ornithine (1), the key constituent of several microbial siderophores, has been synthesized in 23 % yield overall from N-Cbz-L-glutamic acid 1-tert-butyl ester (6) derived from L-glutamic acid. Reduction of 6 to 7 and treatment with N-[(trichloroethoxy)carbonyl]-O-benzylhydroxylamine (8), and diethyl azodicarboxylate and triphenylphosphine followed by deprotection produced the protected N5-acetyl-N5-hydroxy-L-ornithine derivatives 11 and 12 in large quantities (10-20 g). Following alpha-amino and alpha-carboxyl deprotections of 11 and 12, EEDQ [2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline] mediated peptide coupling and final deprotection provided amino acid 1 and six albomycin-like peptides (20, 23, 25, 28, 35, and 36). The growth-promoting ability of each was evaluated with the siderophore biosynthesis mutant Shigella flexneri SA240 (SA 100 iucD:Tn5). These results indicate that substantial modification of the framework of peptide-based siderophores can be tolerated by microbial iron-transport systems.
• US3947274A
  申请人：——

  公开号：US3947274A

  公开（公告）日：1976-03-30