dimethyl 2-amino-9-iodophenoxazin-3-one 1,10-dicarboxylate | 34105-78-7

• 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: dimethyl 2-amino-9-iodophenoxazin-3-one 1,10-dicarboxylate
• 英文别名: 1,9-dicarbomethoxy-2-amino-3H-phenoxazin-3-one；2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid dimethyl ester；2-Amino-3-oxo-3H-phenoxazin-1,9-dicarbonsaeure-dimethylester；2-Amino-1,9-dimethoxycarbonyl-phenoxazon-(3)；Cinnabarinsaeure-methylester；cinnabarinic acid dimethyl ester；Dimethyl 2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylate；dimethyl 2-amino-3-oxophenoxazine-1,9-dicarboxylate
• CAS: 34105-78-7
• 化学式: C₁₆H₁₂N₂O₆
• 分子量: 328.281
• InChiKey: FJGDFTXAJSTDKU-UHFFFAOYSA-N

物化性质

• 熔点：
  225-226 °C (decomp)
• 沸点：
  529.8±50.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl 2-amino-9-iodophenoxazin-3-one 1,10-dicarboxylate 在 硫酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 1.5h， 生成 1,8,13-triacetyltriphenodioxazine
  参考文献：
  名称：

  Formation of dihydrotriphenodioxazines and dihydroisotriphenodioxazines by acidic treatment of some substituted 3H-phenoxazin-3-ones; isolation and characterization. A new perspective in the chemistry of ommochromes

  摘要：

  DOI：

  10.1021/jo00169a006
• 作为产物：
  描述：

  3-羟基-2-硝基苯甲酸 在 palladium 10% on activated carbon 、 氢气 、 potassium hydrogencarbonate 、 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 aq. phosphate buffer 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 dimethyl 2-amino-9-iodophenoxazin-3-one 1,10-dicarboxylate
  参考文献：
  名称：

  Aminophenoxazinones as Inhibitors of Indoleamine 2,3-Dioxygenase (IDO). Synthesis of Exfoliazone and Chandrananimycin A

  摘要：

  A range of 2-aminophenoxazin-3-ones has been prepared by oxidative cyclocondensation of 2-aminophenols, including the natural products exfoliazone and chandrananimycin A, both synthesized for the first time. The compounds were evaluated for their ability to inhibit indoleamine 2,3-dioxygenase. Compounds containing additional electron-withdrawing carboxylate groups, such as cinnabarinic acid, showed modest inhibitory activity with a dose response.

  DOI：

  10.1021/jm400049z

文献信息

• Enantioselective Total Syntheses of Plectosphaeroic Acids B and C
  作者：Salman Y. Jabri、Larry E. Overman

  DOI：10.1021/jo4015479

  日期：2013.9.6

  of the structurally unique plectosphaeroic acids B (2) and C (3) is described. The successful enantioselective route to (+)-2 and (+)-3 proceeds in 6 and 11 steps from the known hexahydro-2H-pyrazinopyrrolo[2,3-b]indole-1,4-dione 39, which in turn is available in enantiomerically pure form by chemical synthesis. The central challenge in this synthesis endeavor was uniting the hexahydro-2H-pyrazinopyrrolo[2

  描述了合成策略的演变，最终实现了结构独特的多聚球酸 B ( 2 ) 和 C ( 3 ) 的首次全合成。从已知的六氢-2H-吡嗪并吡咯并[2,3- b ]吲哚-1,4-二酮39开始，成功的对映选择性路线（+）- 2和（+）- 3分 6 步和 11 步进行，进而通过化学合成可获得对映体纯形式。该合成工作的核心挑战是将这些海洋生物碱的六氢-2H-吡嗪并[2,3- b ]吲哚-1,4-二酮和朱砂酸片段结合起来。成功形成 C-N 键的关键是使用碘肉桂酸二酯，其中氨基被两个 Boc 取代基、羧酸铜 (I) 络合物和弱碱性 KOAc 掩蔽。这种偶联中产生的高度拥挤的 C-N 键，与密集官能化偶联伙伴的微妙性质相结合，有力地证明了现代铜介导的胺化方法的威力。开发了两种方法，一种是立体选择性的，用于引入 (+)-多聚球酸 B 的甲硫基取代基。 (+)-聚球酸C的环三硫环是通过环二硫前体的扩环而形成的。
• Angyal et al., Journal of the Chemical Society, 1957, p. 1592,1599
  作者：Angyal et al.

  DOI：——

  日期：——
• BOLOGNESE, A.;PISCITELLI, C.;SCHERILLO, G., J. ORG. CHEM., 1983, 48, N 21, 3649-3652
  作者：BOLOGNESE, A.、PISCITELLI, C.、SCHERILLO, G.

  DOI：——

  日期：——
• Formation of dihydrotriphenodioxazines and dihydroisotriphenodioxazines by acidic treatment of some substituted 3H-phenoxazin-3-ones; isolation and characterization. A new perspective in the chemistry of ommochromes
  作者：Adele Bolognese、Carlo Piscitelli、Giulia Scherillo

  DOI：10.1021/jo00169a006

  日期：1983.10
• Aminophenoxazinones as Inhibitors of Indoleamine 2,3-Dioxygenase (IDO). Synthesis of Exfoliazone and Chandrananimycin A
  作者：Raffaele Pasceri、David Siegel、David Ross、Christopher J. Moody

  DOI：10.1021/jm400049z

  日期：2013.4.25

  A range of 2-aminophenoxazin-3-ones has been prepared by oxidative cyclocondensation of 2-aminophenols, including the natural products exfoliazone and chandrananimycin A, both synthesized for the first time. The compounds were evaluated for their ability to inhibit indoleamine 2,3-dioxygenase. Compounds containing additional electron-withdrawing carboxylate groups, such as cinnabarinic acid, showed modest inhibitory activity with a dose response.