6-chloro-3-cyclohexyl-2-cyclohexylimino-2,3-dihydro-benzo[e][1,3]oxazin-4-one | 16281-48-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 6-chloro-3-cyclohexyl-2-cyclohexylimino-2,3-dihydro-benzo[e][1,3]oxazin-4-one
• 英文别名: 2-Cyclohexylimino-3-cyclohexyl-4-oxo-6-chlor-2H-3,4-dihydro-benzo-oxazin-(1,3)；6-Chloro-3-cyclohexyl-2-cyclohexylimino-1,3-benzoxazin-4-one
• CAS: 16281-48-4
• 化学式: C₂₀H₂₅ClN₂O₂
• 分子量: 360.884
• InChiKey: XLVTXWWYVKERDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-3-cyclohexyl-2-cyclohexylimino-2,3-dihydro-benzo[e][1,3]oxazin-4-one 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 6-chloro-3-cyclohexyl-benzo[e][1,3]oxazine-2,4-dione
  参考文献：
  名称：

  rat曲霉毒素A和B的合成：曲霉Wilh的代谢产物

  摘要：

  结构IA最近提出了赭曲霉毒素A，主要毒性代谢产物赭曲霉WILH。通过明确的合成证明了该化合物的结构。合成序列的修饰导致相关的酸acid曲霉毒素B（II）。

  DOI：

  10.1016/s0040-4020(01)88843-8
• 作为产物：
  描述：

  5-氯代水杨酸 、 N,N'-二环己基碳二亚胺 以 乙酸乙酯 为溶剂， 生成 6-chloro-3-cyclohexyl-2-cyclohexylimino-2,3-dihydro-benzo[e][1,3]oxazin-4-one
  参考文献：
  名称：

  rat曲霉毒素A和B的合成：曲霉Wilh的代谢产物

  摘要：

  结构IA最近提出了赭曲霉毒素A，主要毒性代谢产物赭曲霉WILH。通过明确的合成证明了该化合物的结构。合成序列的修饰导致相关的酸acid曲霉毒素B（II）。

  DOI：

  10.1016/s0040-4020(01)88843-8

文献信息

• 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.
• The synthesis of ochratoxins A and B
  作者：P.S. Steyn、C.W. Holzapfel

  DOI：10.1016/s0040-4020(01)88843-8

  日期：1967.1

  Structure Ia was recently proposed for ochratoxin A, the main toxic metabolite of Aspergillus ochraceus Wilh. The structure of this compound is proved by an unambiguous synthesis. Modification of the synthetic sequence led to the related acid, ochratoxin B (II).

  结构IA最近提出了赭曲霉毒素A，主要毒性代谢产物赭曲霉WILH。通过明确的合成证明了该化合物的结构。合成序列的修饰导致相关的酸acid曲霉毒素B（II）。