| 57137-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 57137-69-6
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: SEABYWPOHLTIGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-碘苯酚 、 一氧化碳 、 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex potassium carbonate 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 为溶剂， 100.0 ℃ 、2.07 MPa 条件下， 反应 48.0h， 以93%的产率得到2-Butylimino-3-(2,6-dimethylphenyl)-1,3-benzoxazin-4-one
  参考文献：
  名称：

  Palladium-Catalyzed Cyclocarbonylation of o-Iodophenols and 2-Hydroxy-3-iodopyridine with Heterocumulenes:  Regioselective Synthesis of Benzo[e]-1,3-oxazin-4-one and Pyrido[3,2-e]-1,3-oxazin-4-one Derivatives

  摘要：

  Benzo[e]-1,3-oxazin-2-imine-4-ones (3) were synthesized by cyclocarbonylation of o-iodophenols with carbodiimides in the presence of a catalytic amount of a palladium catalyst and 1,4-bis(diphenylphosphino)butane under CO pressure. Product yields are dependent on the nature of the substrate, catalyst, solvent, and base as well as phosphine ligand. Reaction of o-iodophenols with unsymmetrical carbodiimides affords benzo[e]-1,3-oxazin-2-imine-4-ones (11a-g) in good yield and usually in a completely regioselective manner. Benzo[e]-1,3-oxazin-2,4-diones (5) were obtained in good to excellent yields using the same procedure and a 1:2 ratio of o-iodophenol/isocyanate. Pyrido[3,2-e]-1,3-oxazin-4-ones (16) were isolated in fine yield using 2-hydroxy-3-iodopyridine instead of an iodophenol as reactant. The reaction mechanism is believed to involve in situ formation of a carbamate eater followed by palladium-catalyzed carbonylative amidation.

  DOI：

  10.1021/jo991256u
• 作为产物：
  描述：

  1-丁基-3-(2,6-二甲基苯基)脲 在 三乙胺 、 二溴三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Highly Enantioselective Synthesis of 1,3-Oxazolidin-2-imine Derivatives by Asymmetric Cycloaddition Reactions of Vinyloxiranes with Unsymmetrical Carbodiimides Catalyzed by Palladium(0) Complexes

  摘要：

  4-Vinyl-1,3-oxazoilidin-2-imine derivatives have been synthesized by cycloaddition reactions of 2-vinyloxiranes with unsymmetrical carbodiimides catalyzed by palladium(0) complexes-in excellent total isolated yields. After reaction two compounds were always formed, one of which was isolated as the major product. A bulky alkyl group on one of the nitrogen atoms of the carbodiimide enhanced the product ratio in favor of the N-aryl-3-alkyl-1,3-oxazolidin-2-imine. Highly enantioselective cycloadducts (up to >99% ee) were formed by using TolBINAP as the chiral phosphine ligand, in THF at ambient temperatures. The enantiodetermination is believed to be dependent on nucleophilic attack of the anionic nitrogen of the carbodiimide due to the steric interaction of the carbodiimide substituents with the chiral phosphine ligand.

  DOI：

  10.1021/jo9804341

文献信息

• The reaction of isocyanide—mercuric chloride complexes with amines. Preparation of guanidines
  作者：Hiroaki Sawai、Takeo Takizawa

  DOI：10.1016/s0022-328x(00)86941-7

  日期：1975.8

  Isocyanide—mercuric chloride complexes react readily with an excess of primary and secondary amines to give guanidines and metallic mercury in high yields through a redox decomposition reaction. In the presence of triethylamine, isocyanide—mercuric chloride complexes react with an equimolar amount of a primary amine to give a carbodiimide and metallic mercury. An intermediate organomercuric compound

  异氰化物-氯化汞配合物容易与过量的伯胺和仲胺反应，通过氧化还原分解反应以高收率得到胍和金属汞。在三乙胺的存在下，异氰化物-氯化汞配合物与等摩尔量的伯胺反应，生成碳二亚胺和金属汞。在异氰化物-氯化汞配合物与吡咯烷酮的反应中分离出中间体有机汞化合物。
• Palladium-Catalyzed Cyclocarbonylation of <i>o</i>-Iodophenols and 2-Hydroxy-3-iodopyridine with Heterocumulenes:  Regioselective Synthesis of Benzo[<i>e</i>]-1,3-oxazin-4-one and Pyrido[3,2-<i>e</i>]-1,3-oxazin-4-one Derivatives
  作者：Chitchamai Larksarp、Howard Alper

  DOI：10.1021/jo991256u

  日期：1999.12.1

  Benzo[e]-1,3-oxazin-2-imine-4-ones (3) were synthesized by cyclocarbonylation of o-iodophenols with carbodiimides in the presence of a catalytic amount of a palladium catalyst and 1,4-bis(diphenylphosphino)butane under CO pressure. Product yields are dependent on the nature of the substrate, catalyst, solvent, and base as well as phosphine ligand. Reaction of o-iodophenols with unsymmetrical carbodiimides affords benzo[e]-1,3-oxazin-2-imine-4-ones (11a-g) in good yield and usually in a completely regioselective manner. Benzo[e]-1,3-oxazin-2,4-diones (5) were obtained in good to excellent yields using the same procedure and a 1:2 ratio of o-iodophenol/isocyanate. Pyrido[3,2-e]-1,3-oxazin-4-ones (16) were isolated in fine yield using 2-hydroxy-3-iodopyridine instead of an iodophenol as reactant. The reaction mechanism is believed to involve in situ formation of a carbamate eater followed by palladium-catalyzed carbonylative amidation.
• Highly Enantioselective Synthesis of 1,3-Oxazolidin-2-imine Derivatives by Asymmetric Cycloaddition Reactions of Vinyloxiranes with Unsymmetrical Carbodiimides Catalyzed by Palladium(0) Complexes
  作者：Chitchamai Larksarp、Howard Alper

  DOI：10.1021/jo9804341

  日期：1998.9.1

  4-Vinyl-1,3-oxazoilidin-2-imine derivatives have been synthesized by cycloaddition reactions of 2-vinyloxiranes with unsymmetrical carbodiimides catalyzed by palladium(0) complexes-in excellent total isolated yields. After reaction two compounds were always formed, one of which was isolated as the major product. A bulky alkyl group on one of the nitrogen atoms of the carbodiimide enhanced the product ratio in favor of the N-aryl-3-alkyl-1,3-oxazolidin-2-imine. Highly enantioselective cycloadducts (up to >99% ee) were formed by using TolBINAP as the chiral phosphine ligand, in THF at ambient temperatures. The enantiodetermination is believed to be dependent on nucleophilic attack of the anionic nitrogen of the carbodiimide due to the steric interaction of the carbodiimide substituents with the chiral phosphine ligand.