3,4-dihydro-3-hydroxy-6-iodo-4-oxo-1,2,3-benzotriazine | 132533-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并-1,2,3-三嗪类化合物
• 英文名称: 3,4-dihydro-3-hydroxy-6-iodo-4-oxo-1,2,3-benzotriazine
• 英文别名: 3-hydroxy-6-iodobenzo[1,2,3]triazin-4(3H)-one；3-Hydroxy-6-iodo-1,2,3-benzotriazin-4-one
• CAS: 132533-57-4
• 化学式: C₇H₄IN₃O₂
• 分子量: 289.032
• InChiKey: IRFXXWDSKDZAAV-UHFFFAOYSA-N

物化性质

• 熔点：
  170-171 °C (decomp)
• 沸点：
  443.3±47.0 °C(Predicted)
• 密度：
  2.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diphenyliodonium triflate 、 3,4-dihydro-3-hydroxy-6-iodo-4-oxo-1,2,3-benzotriazine 在 potassium tert-butylate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.08h， 以27%的产率得到6-iodo-3-phenoxybenzo[1,2,3]triazin-4(3H)-one
  参考文献：
  名称：

  Tandem C–O and C–N Bonds Formation Through O-Arylation and [3,3]-Rearrangement by Diaryliodonium Salts: Synthesis of N-Aryl Benzo[1,2,3]triazin-4(1H)-one Derivatives

  摘要：

  Metal-free O-arylation and [3, 3]-rearrangement have been shown as an efficient strategy to construct new C-O and C-N bonds in one-pot reactions. The method was used to prepare N-aryl benzo[1,2,3]triazin-4(1H)-one derivatives in good yields from N-hydroxy benzo[1,2,3]triazin-4(3H)-one and diaryliodonium salts. The reaction was tolerated a variety of sensitive functional groups such as iodine, nitro, ester, and aldehyde groups. A rational mechanism was proposed based on the experimental results, and the reaction was easily up to gram scale.

  DOI：

  10.1021/acs.joc.5b01947
• 作为产物：
  描述：

  5-Iodoanthranilichydroxamic acid 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 以4.32 g的产率得到3,4-dihydro-3-hydroxy-6-iodo-4-oxo-1,2,3-benzotriazine
  参考文献：
  名称：

  Tandem C–O and C–N Bonds Formation Through O-Arylation and [3,3]-Rearrangement by Diaryliodonium Salts: Synthesis of N-Aryl Benzo[1,2,3]triazin-4(1H)-one Derivatives

  摘要：

  Metal-free O-arylation and [3, 3]-rearrangement have been shown as an efficient strategy to construct new C-O and C-N bonds in one-pot reactions. The method was used to prepare N-aryl benzo[1,2,3]triazin-4(1H)-one derivatives in good yields from N-hydroxy benzo[1,2,3]triazin-4(3H)-one and diaryliodonium salts. The reaction was tolerated a variety of sensitive functional groups such as iodine, nitro, ester, and aldehyde groups. A rational mechanism was proposed based on the experimental results, and the reaction was easily up to gram scale.

  DOI：

  10.1021/acs.joc.5b01947

文献信息

• EP4 receptor inhibitors to treat rheumatoid arthritis
  申请人：——

  公开号：US20020077329A1

  公开（公告）日：2002-06-20

  The invention features a method of treating rheumatoid arthritis in a mammal comprising administering an agent that inhibits prostaglandin EP4 receptor (EP4) activity. Also featured is a method of identifying agents that selectively inhibit EP4 activity in vivo.

  该发明涉及一种治疗哺乳动物类风湿性关节炎的方法，包括给予一种抑制前列腺素EP4受体（EP4）活性的药物。还涉及一种识别在体内选择性抑制EP4活性的药物的方法。
• A Facile One-Pot Synthesis of 3,4-Dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine and Derivatives
  作者：Mogens Havsteen Jakobsen、Ole Buchardt、Arne Holm、Morten Meldal

  DOI：10.1055/s-1990-27078

  日期：——

  A new one-pot synthesis of 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine (Dhbt-OH) and derivatives directly from anthranilic acids is described. The reaction of anthranilic acids and thionyl chloride affords unstable sulfinamide anhydrides which are treated with O-(trimethylsilyl)hydroxylamine followed by diazotization to give the corresponding Dhbt-OH derivatives in good overall yield.

  本研究描述了一种直接从蒽酸一步合成 3,4-二氢-3-羟基-4-氧代-1,2,3-苯并三嗪（Dhbt-OH）及其衍生物的新方法。蚁酸和亚硫酰氯反应生成不稳定的亚磺酰胺酸酐，这些酸酐经 O-(三甲基硅烷基)羟胺处理后再重氮化，可得到相应的 Dhbt-OH 衍生物，总收率很高。
• Catalyst comprising a nitrogen-containing heterocylic compound
  申请人：Daicel Chemical Industries, Ltd.

  公开号：EP1085015A2

  公开（公告）日：2001-03-21

  A catalyst is for use in a reaction using an oxygen-atom-containing reactant arid includes a nitrogen-containing heterocyclic compound of the following formula (1): wherein each of R1 and R2 is, identical to or different from each other, a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, an aryl group, a cycloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, or an acyl group, and R1 and R2 may be combined to form a double bond or to form an aromatic or non-aromatic ring with the adjacent two carbon atoms, where one or two of heterocyclic ring containing three nitrogen atoms indicated in the formula may be further formed on the R1 or R2, or on the double bond or aromatic or non-aromatic ring formed by R1 and R2; X is an oxygen atom or a hydroxyl group; and Y is a single bond, a methylene group, or a carbonyl group. This catalyst can introduce an oxygen-atom-containing group into an organic substrate under mild conditions.

  一种催化剂用于使用含氧原子的反应物的反应，包括下式(1)的含氮杂环化合物： 其中 R1 和 R2 各自是相同或不同的氢原子、卤素原子、烷基、卤代烷基、芳基、环烷基、羟基、烷氧基、羧基、烷氧羰基或酰基、且 R1 和 R2 可结合形成双键，或与相邻的两个碳原子形成芳香环或非芳香环，其中 R1 或 R2 上，或 R1 和 R2 形成的双键或芳香环或非芳香环上可进一步形成式中所示的含有三个氮原子的杂环中的一个或两个；X 是氧原子或羟基；Y 是单键、亚甲基或羰基。这种催化剂可以在温和的条件下将含氧原子的基团引入有机底物中。
• JAKOBSEN, MOGENS HAVSTEEN;BUCHARDT, OLE;HOLM, ARNE;MELDAL, MORTEN, SYNTHESIS,(1990) N1, C. 1008-1010
  作者：JAKOBSEN, MOGENS HAVSTEEN、BUCHARDT, OLE、HOLM, ARNE、MELDAL, MORTEN

  DOI：——

  日期：——
• US6403521B1
  申请人：——

  公开号：US6403521B1

  公开（公告）日：2002-06-11