2-苯氧基-1,4-苯醌 | 3490-49-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-苯氧基-1,4-苯醌
• 英文名称: 2-phenoxy-1,4-benzoquinone
• 英文别名: 2-Phenoxycyclohexa-2,5-diene-1,4-dione
• CAS: 3490-49-1
• 化学式: C₁₂H₈O₃
• 分子量: 200.194
• InChiKey: YKYILJANBFCBQH-UHFFFAOYSA-N

物化性质

• 熔点：
  71 °C
• 沸点：
  313.3±31.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  2-苯氧基-1,4-苯醌 在 溶剂黄146 、 锌 作用下， 生成 2-phenoxy-1,4-dihydroquinone
  参考文献：
  名称：

  PHENOXYQUINONES. 1. 2-PHENOXY-p-BENZOQUINONE AND 2-PHENOXY-5-METHYL-p-BENZOQUINONE

  摘要：

  DOI：

  10.1021/jo01151a030
• 作为产物：
  描述：

  2,4,6-三氯苯酚 在 30percent Pd/C chromium(VI) oxide 、 盐酸 、 calcium hypochlorite 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 5.58h， 生成 2-苯氧基-1,4-苯醌
  参考文献：
  名称：

  Formation of Dimer-Type Ketals in the Reaction of 2,4,6-Trichlorophenol and 2,4,6-Trichloro-m-cresol with Calcium Hypochlorite in Methanol:  Conversion to Quinones and Other Compounds

  摘要：

  2,4,6-Trichlorophenol (2) and 2,4,6-trichloro-m-cresol (5) react with calcium hypochlorite (Ca(OCl)(2)) in MeOH to give respectively dimer-type ketals 2-(2',4',6'-trichlorophenoxy)-4,4-dimethoxy-6-chlorocyclohexadien-2,5- one (6) and 2-(3'-methyl-2',4',6'-trichlorophenoxy)-4,4-dimethoxy-5-methyl-6-chlorocyclohexadien-2,5-one (7). Ketal 6, which was too unstable to be isolated, and 7 hydrolyzed in H2O/HCl to 2-(2',4',6'-trichlorophenoxy)-6-chloro-1,4-benzoquinone (8) and 2-(3'-methyl-2',4',6'-trichlorophenoxy)-5methyl-6-chloro-1,4-benzoquinone (9), respectively. Ketal 6 and quinone 8 were also produced when 2 and Ca(OCl)(2) reacted in DMF, followed by addition of MeOH and H2O, respectively. The mechanisms of these reactions are examined. Conversion of the ketals and quinones to other products is described.

  DOI：

  10.1021/jo020311n

文献信息

• Unified Synthesis of Quinone Sesquiterpenes Based on a Radical Decarboxylation and Quinone Addition Reaction
  作者：Taotao Ling、Erwan Poupon、Erik J. Rueden、Sun H. Kim、Emmanuel A. Theodorakis

  DOI：10.1021/ja027517q

  日期：2002.10.1

  several quinone sesquiterpenes is described herein. Essential to this strategy is a novel radical addition reaction that permits the attachment of a fully substituted bicyclic core 16 to a variably substituted quinone 10. The addition product 15 can be further functionalized, giving access to natural products with a high degree of oxygenation at the quinone unit. The quinone addition reaction is characterized

  本文描述了几种醌倍半萜的统一合成。该策略的关键是一种新的自由基加成反应，它允许将完全取代的双环核 16 连接到可变取代的醌 10。加成产物 15 可以进一步官能化，从而获得具有高度氧化的天然产物醌单位。醌加成反应的特点是优异的化学选择性，仅发生在共轭和未取代的双键上，区域选择性受到位于醌环上的杂原子的共振效应的强烈影响。这些特征已成功应用于阿瓦罗 (1)、阿瓦隆 (2)、甲氧阿瓦隆 (4、5)、伊马醌 (6) 和 smenospongidine (7) 的合成，从而证明了这种新方法的合成价值。
• Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C–H Iodination, Bromination, and Phenylselenation
  作者：Guilherme A. M. Jardim、John F. Bower、Eufrânio N. da Silva Júnior

  DOI：10.1021/acs.orglett.6b01586

  日期：2016.9.16

  4-benzoquinones exhibit nucleophilic reactivity, such that exposure to appropriate electrophiles generates products of C–H iodination, bromination, and phenylselenation. This provides a mild and general method for direct halofunctionalization, and the first method that can achieve direct C–H phenylselenation of this compound class. The scope and limitations of the new protocols are outlined, and representative

  在Rh催化的条件下，典型的亲电子1,4-苯醌具有亲核反应性，因此暴露于适当的亲电子会产生CH碘化，溴化和苯硒化的产物。这为直接的卤代官能化提供了一种温和而通用的方法，并且是第一个可以实现此类化合物直接C–H苯基硒化的方法。概述了新协议的范围和局限性，并突出了代表性的衍生化。
• A new route to isodityrosine-derived cyclic peptides: Application to K-13
  作者：A.V.Rama Rao、Mukund K. Gurjar、A.Bhaskar Reddy、Vivek B. Khare

  DOI：10.1016/0040-4039(93)85034-t

  日期：1993.3

  A versatile approach suitable for isodityrosine derived cyclic peptides, and its application to K-13 have been described.

  已经描述了适用于异酪氨酸衍生的环肽的通用方法及其在K-13中的应用。
• Process for producing three-dimensionally crosslinked polyester having the liquid crystal structure
  申请人：POLYPLASTICS CO. LTD.

  公开号：EP0249662A1

  公开（公告）日：1987-12-23

  A polyester, being capable of the anisotropic property in the molten state and a thermotropic liquid crystals, or a composition comprising a low molecular weight polyester and a thermotropic liquid crystal mixture is three dimensionally crosslinked, while having the structure of liquid crystals, by a crosslinking reaction with a compound having at least three reactive groups. The reactive group preferably includes hydroxy, carboxyl, amino, amide, carbodiimide, isocyanate, carbamate, epoxy and ester.

  一种在熔融状态下具有各向异性和各向同性液晶的聚酯，或一种由低分子量聚酯和各向同性液晶混合物组成的组合物，在具有液晶结构的同时，通过与一种至少有三个反应基团的化合物发生交联反应而实现三维交联。活性基团最好包括羟基、羧基、氨基、酰胺、碳化二亚胺、异氰酸酯、氨基甲酸酯、环氧基和酯。
• DE963153
  申请人：——

  公开号：——

  公开（公告）日：——