4-hydroxy-7-methyl-2H,5H-pyrano[4,3-b]pyran-2,5-dione | 4860-88-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-hydroxy-7-methyl-2H,5H-pyrano[4,3-b]pyran-2,5-dione
• 英文别名: 4-hydroxy-7-methyl-pyrano[4,3-b]pyran-2,5-dione；4-hydroxy-7-methylpyrano[3,2-c]pyran-2,5-dione
• CAS: 4860-88-2
• 化学式: C₉H₆O₅
• 分子量: 194.144
• InChiKey: JVDRIKFYHYUOEY-UHFFFAOYSA-N

物化性质

• 熔点：
  220-221 °C
• 沸点：
  340.7±42.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-7-methyl-2H,5H-pyrano[4,3-b]pyran-2,5-dione 在 水 作用下， 反应 3.0h， 以96%的产率得到去氢乙酸
  参考文献：
  名称：

  Crombie, Leslie; Games, David E.; James, Alun W. G., Journal of the Chemical Society. Perkin transactions I, 1996, # 22, p. 2715 - 2724

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二酮己酸甲酯 在 硫酸 、 三氟乙酸 作用下， 反应 5.0h， 生成 4-hydroxy-7-methyl-2H,5H-pyrano[4,3-b]pyran-2,5-dione
  参考文献：
  名称：

  Crombie, Leslie; Games, David E.; James, Alun W. G., Journal of the Chemical Society. Perkin transactions I, 1996, # 22, p. 2715 - 2724

  摘要：

  DOI：

文献信息

• [4+2] Cycloadditions between 2-pyrones and benzyne. Application to the synthesis of binaphthyls
  作者：Sonia Escudero、Dolores Pérez、Enrique Guitián、Luis Castedo

  DOI：10.1016/s0040-4039(97)01176-3

  日期：1997.7

  Cycloaddition of benzyne to 2-pyrones affords the corresponding naphthalene derivatives, the intermediate bicyclic adduct not being detected. Benzopyrones do not react with benzyne under similar conditions probably because this would require the fused aromatic ring to lose aromaticity in the Diels-Alder transition state, which is therefore destabilized. 4-Bromo-2-naphthoic acid methyl ester (obtained by cycloaddition

  苯并炔与2-吡喃酮的环加成反应得到相应的萘衍生物，未检测到中间体双环加合物。在相似的条件下，苯并吡喃酮不会与苯并react反应，可能是因为这将要求稠合的芳环在Diels-Alder过渡态下失去芳香性，因此不稳定。可以通过Ni介导的方法将4-溴-2-萘甲酸甲酯（通过将苯甲醛环加成至3-溴5-羧甲基吡喃-2-酮而获得）转化为3,3'-二羧甲基-1,1'-联萘基二聚化。
• Pyrone studies—II
  作者：J.L. Douglas、T. Money

  DOI：10.1016/0040-4020(67)80001-2

  日期：1967.1

  Further studies on the use of pyrones for the biogenetic-type synthesis of phenolic compounds are reported. In particular some control over the direction of cyclization of the intermediate β-triketo ester chain is demonstrated. This control makes possible the synthesis of two basic types of phenolic compound from the same precursor and is analogous to the probable biosynthesis of these compounds in

  报道了将吡喃酮用于酚类化合物的生物遗传合成的进一步研究。特别地，证明了对中间β-三酮酸酯链的环化方向的一些控制。这种控制使得从相同的前体中合成两种基本类型的酚类化合物成为可能，并且类似于这些化合物在天然系统中可能的生物合成。
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• The control of pyrone and aromatic cylisation in polyketonic–polyenolic systems by magnesium alkoxide concentration
  作者：L. Crombie、A. W. G. James

  DOI：10.1039/c19660000357

  日期：——
• Convenient Synthesis of Furopyranopyrandione Derivatives by the CAN-mediated Furan Ring Formation
  作者：Kazuhiro Kobayashi、Katsunori Nagase、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.3987/com-02-9690

  日期：——

  4H,9H-Furo[3,2-c]pyrano[3,4-e]pyran-4,9-dione (8) and (10) and 4H,5H-furo[2,3-b]pyrano[3,4-e]pyran-4,5-dione derivatives (9) were prepared in one step by treating 4-hydroxy-2H,5H-pyrano[4,3-b]pyran-2,5-diones (6) and alkenes (7) (or phenylacetylene) in acetonitrile with 2 equivalents of cerium(IV) ammonium nitrate (CAN).