4-hydroxy-5-phenylcyclohexa-3,5-diene-1,2-dione | 23305-16-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-5-phenylcyclohexa-3,5-diene-1,2-dione
• 英文别名: 2-hydroxy-5-phenylcyclohexa-2,5-diene-1,4-dione；2-hydroxy-5-phenyl-1,4-benzoquinone；2-hydroxy-5-phenyl-[1,4]benzoquinone；2-Hydroxy-5-phenyl-[1,4]benzochinon；2-Hydroxy-5-phenyl-1,4-benzochinon
• CAS: 23305-16-0
• 化学式: C₁₂H₈O₃
• 分子量: 200.194
• InChiKey: HWETVAMORRXQRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5-phenylcyclohexa-3,5-diene-1,2-dione 以 二氯甲烷 、 乙腈 为溶剂， 生成 1-Phenyl-3,5-dioxycyclopenten
  参考文献：
  名称：

  The chemistry of 2-oxido-3-phenyliodonio-1,4-benzoquinones: Transformation to 2-cyclopentene-1,4-diones and cycloadditions

  摘要：

  The conversion of substituted 2-hydroxy-1,4-benzoquinones, 1, to 2-cyclopentene-1,4-diones, 3, is effected by thermolysis of their iodonium zwitterions, 2. Some cycloadditions through 2 are also described.

  DOI：

  10.1016/s0040-4039(00)74430-3
• 作为产物：
  描述：

  对羟基联苯 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 1,2-双(叔丁基氨基)乙烷 、 氧气 、 硫酸 、 水 作用下， 以 二氯甲烷 为溶剂， 23.0 ℃ 、101.33 kPa 条件下， 反应 5.08h， 以32%的产率得到4-hydroxy-5-phenylcyclohexa-3,5-diene-1,2-dione
  参考文献：
  名称：

  A divergent and selective synthesis of ortho- and para-quinones from phenols

  摘要：

  We describe a divergent synthesis of substituted ortho- and para-quinones by catalytic aerobic oxygenation of phenols. Substituted quinones are omnipresent in chemistry and biology, but their synthesis frequently suffers from low efficiency and poor scope. Our methodology employs a catalytic aerobic di-functionalization of phenols to aryloxy-ortho-quinones. Regioselective substitution with an alcohol provides the alkoxy substituted ortho- or para-quinone, while hydrolysis affords the para-hydroxyquinone. These are mild and selective conditions for the synthesis of diversely substituted quinones from readily available phenol starting materials. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.04.095

文献信息

• One-Step Synthesis of Naphthofurandione, Benzofurandione, and Phenalenofuranone Derivatives by the CAN-Mediated Cycloaddition
  作者：Kazuhiro Kobayashi、Tomokazu Uneda、Koujirou Tanaka、Masako Mori、Hideo Tanaka、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1246/bcsj.71.1691

  日期：1998.7

  The 3+2-type cycloaddition reaction of 2-hydroxy-1,4-naphthoquinones with various alkenes or phenylacetylene was mediated by ammonium cerium(IV) nitrate (CAN) to give the corresponding naphtho[2,3-b]furan-4,9-dione and naphtho[1,2-b]furan-4,5-dione derivatives. The reaction of 2-hydroxy-1,4-benzoquinones with alkenes in the presence of CAN similarly proceeded to give benzofuran-4,7-dione and benzofuran-4,5-dione derivatives. 3-Hydroxy-1H-phenalen-1-one also underwent the CAN-mediated cycloaddition with alkenes or phenylacetylene to give the corresponding 7H-phenaleno[1,2-b]furan-7-one derivatives.

  2-羟基-1,4-萘醌与各种烯烃或苯乙炔在硝酸铈铵（CAN）的催化下发生3+2型环加成反应，生成相应的萘并[2,3-b]呋喃-4,9-二酮和萘并[1,2-b]呋喃-4,5-二酮衍生物。2-羟基-1,4-苯醌与烯烃在CAN存在下同样发生反应，得到苯并呋喃-4,7-二酮和苯并呋喃-4,5-二酮衍生物。3-羟基-1H-菲兰烯-1-酮也能在CAN的催化下与烯烃或苯乙炔发生环加成反应，生成相应的7H-菲兰诺[1,2-b]呋喃-7-酮衍生物。
• Acid-catalyzed addition of indoles to hydroxyquinones
  作者：Sofia Koulouri、Elizabeth Malamidou-Xenikaki、Spyros Spyroudis

  DOI：10.1016/j.tet.2005.09.003

  日期：2005.11

  Hydroxyquinones react smoothly with substituted indoles in the presence of a catalytic amount of p-toluenesulfonic acid to afford a variety of addition products. The main products are either the corresponding p-quinone or the corresponding hydroquinone, resorcinol and benzenetriol mono- and diindolyl derivatives, depending on the nature of the hydroxyquinone and the substituents on the indole ring

  在催化量的对甲苯磺酸的存在下，羟基醌与取代的吲哚反应平稳，从而提供了多种加成产物。主要产物是相应的对苯醌或相应的氢醌，间苯二酚和苯三醇单和二吲哚基衍生物，这取决于羟基醌的性质和吲哚环上的取代基。
• Access to Aryl‐Naphthaquinone Atropisomers by Phosphine‐Catalyzed Atroposelective (4+2) Annulations of δ‐Acetoxy Allenoates with 2‐Hydroxyquinone Derivatives
  作者：Xin Chen、Dingding Gao、Dong Wang、Tong Xu、Wei Liu、Ping Tian、Xiaofeng Tong

  DOI：10.1002/anie.201908923

  日期：2019.10.21

  of various chiral carbon centers, its synthetic potential toward an enantioenriched atropisomer has not been explored yet. Reported herein is a phosphine-catalyzed atroposelective (4+2) annulation of δ-acetoxy allenoates and 2-hydroxyquinone derivatives. The reaction provides expedient access to aryl-naphthaquinone atropisomers by the de novo construction of a benzene ring. The two functionalities of

  尽管不对称膦催化是构建各种手性碳中心的有力工具，但尚未探索其对映体富对映异构体的合成潜力。本文报道了δ-乙酰氧基烯丙基酯和2-羟基醌衍生物的膦催化的对映选择性（4 + 2）环化。通过苯环的从头构建，该反应提供了便利的芳基-萘醌阻转异构体的途径。催化剂的两种官能度，叔膦（刘易斯碱）和叔胺（布朗斯台德碱）共同使该方法具有很高的区域选择性和对映选择性。
• Fieser et al., Journal of the American Chemical Society, 1948, vol. 70, p. 3177
  作者：Fieser et al.

  DOI：——

  日期：——
• 1013. Thiele acetylation of 2-phenyl-1,4-benzoquinone and its 5-methoxy-derivative
  作者：J. M. Blatchly、J. F. W. McOmie

  DOI：10.1039/jr9630005311

  日期：——