1,1'-di-p-tolyl-1H,1'H-[1,1']biisobenzofuranyl-3,3'-dione | 96375-12-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,1'-di-p-tolyl-1H,1'H-[1,1']biisobenzofuranyl-3,3'-dione
• 英文别名: 1,1'-Di-p-tolyl-1H,1'H-[1,1']biisobenzofuranyl-3,3'-dion；3-(4-Methylphenyl)-3-[1-(4-methylphenyl)-3-oxo-2-benzofuran-1-yl]-2-benzofuran-1-one
• CAS: 96375-12-1
• 化学式: C₃₀H₂₂O₄
• 分子量: 446.502
• InChiKey: NQIQVQPIQBGQHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  34
• 可旋转键数：
  3
• 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
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4'-methyl-o-benzoylbenzoic acid chloride 在 sodium metabisulfite 、 sodium iodide 作用下， 生成 1,1'-di-p-tolyl-1H,1'H-[1,1']biisobenzofuranyl-3,3'-dione
  参考文献：
  名称：

  持久存在的氧代异苯并呋喃基自由基的制备及ESR光谱研究

  摘要：

  的非对映异构的1,1'-二芳基-1,1'-二（异苯并呋喃）-3,3'（1合成ħ，1' ħ） -二酮3a-d中从开始容易获得的2- aroylbenzoic酸1A-描述了d（方案1）。在无色二聚体3a-d中，只有在空间温度下拥挤的3a和3b在溶液中分别解离为深红色的游离3-氧代异苯并呋喃-1-基自由基4a和4b。自由基4a，b在没有O 2的情况下具有极强的持久性。确认了这些自由基的结构，并通过ESR和ENDOR光谱以及其ESR光谱的计算机模拟确定了耦合常数。甲苯在20°下3a的解离平衡常数确定为1.18·10 -5M。通过研究稳态自由基浓度随温度的变化，确定3a均解离的焓和熵变化。

  DOI：

  10.1002/hlca.19930760503

文献信息

• Acylpalladation of Internal Alkynes and Palladium-Catalyzed Carbonylation of (Z)-.beta.-Iodoenones and Related Derivatives Producing .gamma.-Lactones and .gamma.-Lactams
  作者：Christophe Coperet、Takumichi Sugihara、Guangzhong Wu、Izumi Shimoyama、Ei-ichi Negishi

  DOI：10.1021/ja00117a011

  日期：1995.3

  The reaction of either an internal alkyne-organic halide mixture or (Z)-beta-iodoenones with CO in the presence of a Pd-phosphine catalyst, e.g., Cl2Pd(PPh(3))2, can give one of the three discrete types of compounds as the major products depending on the substrate structure and the reaction conditions. Those substrates which are convertible to (Z)-gamma-oxo-alpha,beta-unsaturated acylpalladium derivatives lacking delta-H atoms are converted to the corresponding 2-butenolides (13) in the presence of water, which serves as a H donor. Carbon monoxide most likely is the source of two electrons. Either in the absence of water (or any other suitable H source) or in the presence of some factors disfavoring the butenolide formation, the same reaction gives the corresponding dimeric product (16). Even in cases where there is an alpha-H atom in the alpha-substitutent, 1,4-elimination products (11), reported to be the major products in a related Pd-catalyzed reaction of terminal alkyne-aryl iodide mixtures with CO, were not detected. In sharp contrast, those substrates which can give rise to (Z)-gamma-oxo-alpha, beta-unsaturated acylpalladium derivatives containing delta-H atoms give, under comparable reaction conditions, enol lactones (12), i.e., (Z)-3-alkylidene-2-butenolides, contaminated with only very minor amounts of 22 even in cases where an excess (4 equiv) of water was present. The required (Z)-beta-iodoenones can be readily prepared in one pot via ZrCp(2)-promoted cyclization of alkynes with nitriles. The ready availability of the starting compounds and the high Z stereoselectivity make the overall sequence an attractive synthetic route to 12. The courses of the Pd-catalyzed carbonylation reactions of (Z)-beta-iodo-alpha,beta-unsaturated imines 23 closely parallel the reactions of enones and produce the corresponding lactams, i.e., 24 and 25.
• Takahashi, Masaki; Fujita, Tsutomu; Watanabe, Shoji, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 3, p. 487 - 491
  作者：Takahashi, Masaki、Fujita, Tsutomu、Watanabe, Shoji、Sakamoto, Masami

  DOI：——

  日期：——
• Thio Compounds Derived from Aroyl-<i>o</i>-benzoic Acids
  作者：John. O'Brochta、Alexander. Lowy

  DOI：10.1021/ja01265a061

  日期：1939.10.1
• Limaye, Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1932, vol. 1/2, p. 52
  作者：Limaye

  DOI：——

  日期：——
• Preparation and ESR-Spectroscopical Investigation of Remarkably Persistent Oxoisobenzofuranyl Radicals
  作者：Gary Kruppa、Paul Hug、André Liégard、Guenther Rist、Petr Nesvadba

  DOI：10.1002/hlca.19930760503

  日期：1993.8.11

  2-aroylbenzoic acids 1a–d is described (Scheme 1). Of the colourless dimers 3a–d, only the sterically congested 3a and 3b dissociate at ambient temperature in solution to the deep red free 3-oxoisobenzofuran-1-yl radicals 4a and 4b, respectively. The radicals 4a, b are extremely persistent in the absence of O2. The structures of these radicals are confirmed and the coupling constants assigned by ESR and ENDOR

  的非对映异构的1,1'-二芳基-1,1'-二（异苯并呋喃）-3,3'（1合成ħ，1' ħ） -二酮3a-d中从开始容易获得的2- aroylbenzoic酸1A-描述了d（方案1）。在无色二聚体3a-d中，只有在空间温度下拥挤的3a和3b在溶液中分别解离为深红色的游离3-氧代异苯并呋喃-1-基自由基4a和4b。自由基4a，b在没有O 2的情况下具有极强的持久性。确认了这些自由基的结构，并通过ESR和ENDOR光谱以及其ESR光谱的计算机模拟确定了耦合常数。甲苯在20°下3a的解离平衡常数确定为1.18·10 -5M。通过研究稳态自由基浓度随温度的变化，确定3a均解离的焓和熵变化。