5,5'-dimethyl-3,3'-diphenyl-3,3'-bibenzo-furan-2,2'-(3H,3'H)-dione | 65425-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 5,5'-dimethyl-3,3'-diphenyl-3,3'-bibenzo-furan-2,2'-(3H,3'H)-dione
• 英文别名: 5,5'-dimethyl-3,3'-diphenyl-3,3'-dibenzofuran-2,2'(3H,3'H)-dione；5,5′-dimethyl-3,3′-diphenyl-3H,3′H[3,3′]-bibenzofuranyl-2,2′-dione；5,5’-dimethyl-3,3’-diphenyl-[3,3’-bibenzofuran]-2,2’(3H,3’H)-dione；5,5'-dimethyl-3,3'-diphenyl-3H,3'H-[3,3']bibenzofuranyl-2,2'-dione；5,5'-Dimethyl-3,3'-diphenyl-3H,3'H-[3,3']bibenzofuranyl-2,2'-dion；5-methyl-3-(5-methyl-2-oxo-3-phenyl-1-benzofuran-3-yl)-3-phenyl-1-benzofuran-2-one
• CAS: 65425-11-8
• 化学式: C₃₀H₂₂O₄
• 分子量: 446.502
• InChiKey: GQCVFPNLEDRSMX-UHFFFAOYSA-N

物化性质

• 沸点：
  531.7±50.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  34.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5,5'-dimethyl-3,3'-diphenyl-3,3'-bibenzo-furan-2,2'-(3H,3'H)-dione 在 邻二氯苯 作用下， 生成
  参考文献：
  名称：

  Some reactions of persistent benzofuranone radicals related to the ‘old’ diazonamide structure

  摘要：

  The benzofuranone dimers 9 and 10/11 readily (ca. 75 degreesC) dissociate to the persistent radicals 16 and 17 respectively, which are stable to, dioxygen. The OMe analog 25 dissociates to form the radical 24, which reacts with dioxygen of TEMPO to give 26. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.11.103
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 铜 、 苯 作用下， 生成 5,5'-dimethyl-3,3'-diphenyl-3,3'-bibenzo-furan-2,2'-(3H,3'H)-dione
  参考文献：
  名称：

  Schmidt, Chemische Berichte, 1928, vol. 61, p. 1349,1351

  摘要：

  DOI：

文献信息

• Cu-Catalyzed Cross-Dehydrogenative Coupling of Heteroaryl C(sp²)–H and Tertiary C(sp³)–H Bonds for the Construction of All-Carbon Triaryl Quaternary Centers
  作者：Zhi Tang、Zhili Liu、Zhou Tong、Zhihui Xu、Chak-Tong Au、Renhua Qiu、Nobuaki Kambe

  DOI：10.1021/acs.orglett.9b01755

  日期：2019.7.5

  A Cu-catalyzed protocol for cross-dehydrogenative coupling of benzofuranones with quinolines, indoles, carbazoles, and thiophene, which furnishes highly functionalized 3,3-diaryl benzofuranones bearing a three aryl quaternary carbon center at the C3 position in good yields, has been developed. A radical mechanism is proposed.

  已开发出一种铜催化的苯并呋喃酮与喹啉，吲哚，咔唑和噻吩的交叉脱氢偶联方案，该方案可提供高产率的高官能度3,3-二芳基苯并呋喃酮，其在C3位置带有三个芳基季碳中心，收率很高。 。提出了一种激进的机制。
• Photochemical and thermal transformations of 2(3H)-furanones and bis(benzofuranones). A laser flash photolysis study
  作者：B. B. Lohray、C. V. Kumar、P. K. Das、M. V. George

  DOI：10.1021/ja00336a010

  日期：1984.11

  Photochemical and thermal transformations of a few 2(3H)-furanones and bis(benzofuranones) were investigated in detail. Laser flash photolysis technique was employed for the first time to examine the mechanistic aspects of these photochemical reactions. Spectral and kinetic data are presented for the triplets of 2(3H)-furanones containing styrene and cis-stilbene moieties constrained into planar geometries

  详细研究了一些 2(3H)-呋喃酮和双 (苯并呋喃酮) 的光化学和热转变。首次采用激光闪光光解技术来检查这些光化学反应的机械方面。提供了 2(3H)-呋喃酮三联体的光谱和动力学数据，其中包含限制在平面几何形状中的苯乙烯和顺二苯乙烯部分。呋喃酮的光解在苯或甲醇溶液中进行。
• Catalytic Oxidation of 3-Arylbenzofuran-2(3<i>H</i>)-ones with PCC-H₅IO₆: Syntheses of 3-Aryl-3-hydroxy/3-amido-3-arylbenzofuran-2(3<i>H</i>)-ones
  作者：Bhaskar B. Dhotare、Mukesh Kumar、Sandip K. Nayak

  DOI：10.1021/acs.joc.8b01395

  日期：2018.9.7

  A pyridinium chlorochromate (PCC)-mediated facile oxidative dimerization of 3-arylbenzofuran-2-ones at ambient temperature was developed which undergo oxidative cleavage to 3-aryl-3-hydroxy-benzofuran-2-ones with PCC at elevated temperatures. Finally, direct oxidation of 3-arylbenzofuran-2-ones to 3-aryl-3-hydroxy-benzofuran-2-ones was realized using a combination of PCC (10 mol %) and 2.0 equiv of

  在环境温度下，开发了氯氰化吡啶鎓（PCC）介导的3-芳基苯并呋喃-2-酮的简便氧化二聚反应，该反应在升高的温度下被PCC氧化裂解为3-芳基-3-羟基-苯并呋喃-2-酮。最后，使用PCC（10mol％）和2.0当量的H 5 IO 6的组合，实现了3-芳基苯并呋喃-2-酮直接氧化为3-芳基-3-羟基-苯并呋喃-2-酮。通过Ritter反应将合成的3-芳基-3-羟基-苯并呋喃酮进一步高产率地转化为相应的3-氨基-3-芳基-苯并呋喃酮。因此，本方案提供了使用催化量的廉价铬（VI）氧化剂通过其二聚体对3-芳基苯并呋喃酮进行C-3羟基化的非常规方法。
• I₂-Mediated Cross-Dehydrogenative Coupling and Amidation of 3-Aryl Benzofuranones with Aryl Amines for the Synthesis of 3,3-Diaryl Indolin-2-ones
  作者：Zhi Tang、Zhiqing Wang、Zhihong Peng、Qinghua Yang、Shuang-Feng Yin、Renhua Qiu

  DOI：10.1021/acs.joc.0c02846

  日期：2021.2.5

  We have developed a protocol for efficient synthesis of indolin-2-ones from benzofuranones and aryl amines using iodine as a mediator. A diverse range of benzofuranones and aryl amines undergo cross-dehydrogenative coupling and amidation of 3-aryl benzofuranones for the cascade reaction to generate products in 24–93% yields. This reaction can be easily scaled-up to give an indolin-2-one in a gram scale

  我们已经开发了使用碘作为介体从苯并呋喃酮和芳基胺高效合成吲哚-2-酮的方案。各种各样的苯并呋喃酮和芳基胺经过交叉脱氢偶联和3-芳基苯并呋喃酮的酰胺化反应进行级联反应，以24-93％的产率生成产物。该反应可以容易地按比例放大以得到克级的吲哚-2-酮。对产物进行进一步的化学处理可实现酚环的有用转化，包括烷基化，芳基化等。
• Cu(I)-Catalyzed C–H Alkenylation of Tertiary C(sp³)–H Bonds of 3-Aryl Benzofuran-2(<i>3H</i>)-ones to Give <i>Z</i>- and <i>E</i>-Styrene Containing Quaternary Carbon Centers with 99/1 Regioselectivity
  作者：Zhou Tong、Xinju Peng、Lifen Peng、Wei Deng、Zhiqing Wang、Hao Lu、Weijun Yang、Shuang-Feng Yin、Nobuaki Kambe、Renhua Qiu

  DOI：10.1021/acs.joc.2c00325

  日期：2022.5.6

  all-carbon quaternary centers is a challenging issue. Herein, we developed an efficient protocol for the synthesis of (Z)-olefins (27 examples, yield up to 97%, Z/E up to 99/1) and (E)-olefins (16 examples, yield up to 94%, E/Z up to 99/1) containing all-carbon quaternary centers. This protocol is adopted for the copper-catalyzed regioselective C–H alkenylation of the tertiary C(sp3)–H bond of 3-aryl

  含有全碳季中心的异构纯烯烃的合成是一个具有挑战性的问题。在此，我们开发了一种用于合成 ( Z )-烯烃（27 个示例，产率高达 97%，Z / E高达 99/1）和 ( E )-烯烃（16 个示例，产率高达 94%）的有效方案, E / Z高达 99/1) 含有全碳四元中心。该方案适用于铜催化的 3-芳基苯并呋喃-2( 3H )-酮与炔烃和烯烃的叔 C(sp 3 )-H 键的区域选择性 C-H 烯基化。底物中的多种官能团具有良好的耐受性，例如 F、Cl、Br、Me、OMe、酯、CF 3等。以良好的产量进行了克级实验，并在对照实验的基础上提出了激进机制。