二苯酮-4,4-二甲酸二乙酯 | 1797-82-6

• 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: 二苯酮-4,4-二甲酸二乙酯
• 英文名称: 4,4'-diethoxycarbonylbenzophenone
• 英文别名: diethyl 4,4'-benzophenonedicarboxylate；bis(4-carbethoxyphenyl)methanone；diethyl 4,4′-carbonyldibenzoate；Diethyl 4,4'-carbonyldibenzoate；ethyl 4-(4-ethoxycarbonylbenzoyl)benzoate
• CAS: 1797-82-6
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: FEDHHDIXLPGIMX-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  473.3±30.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2918300090
• 储存条件：
  紧封贮藏器存放在阴凉干燥处，并远离氧化剂。

反应信息

• 作为反应物：
  描述：

  二苯酮-4,4-二甲酸二乙酯 在 锂硼氢 、 偶氮二甲酸二异丙酯 、 三乙基硼氢化锂 、 臭氧 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 正戊烷 为溶剂， 反应 72.0h， 生成 adamantane-2-spiro-3'-5',5'-bis[4'-(aminomethyl)phenyl]-1',2',4'-trioxolane
  参考文献：
  名称：

  Effect of functional group polarity on the antimalarial activity of spiro and dispiro-1,2,4-trioxolanes

  摘要：

  Based on the structures of several lipophilic trioxolane antimalarial prototypes, we set out to determine which functional groups were associated with good antimalarial profiles and identify more polar (lower LogP/LogD) lead compounds with good physicochemical properties. More lipophilic trioxolanes tended to have better oral activities than their more polar counterparts. Trioxolanes with a wide range of neutral and basic, but not acidic, functional groups had good antimalarial profiles. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.041
• 作为产物：
  描述：

  4,4'-二甲基二苯甲酮 在 potassium permanganate 、 硫酸 作用下， 以 甲苯 为溶剂， 生成 二苯酮-4,4-二甲酸二乙酯
  参考文献：
  名称：

  Effect of functional group polarity on the antimalarial activity of spiro and dispiro-1,2,4-trioxolanes

  摘要：

  Based on the structures of several lipophilic trioxolane antimalarial prototypes, we set out to determine which functional groups were associated with good antimalarial profiles and identify more polar (lower LogP/LogD) lead compounds with good physicochemical properties. More lipophilic trioxolanes tended to have better oral activities than their more polar counterparts. Trioxolanes with a wide range of neutral and basic, but not acidic, functional groups had good antimalarial profiles. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.041

文献信息

• One-Pot Synthesis of Diarylmethanones through Palladium-Catalyzed Sequential Coupling and Aerobic Oxidation of Aryl Bromides with Acetophenone as a Latent Carbonyl Donor
  作者：Xing Wang、Fu-Di Liu、Hai-Yang Tu、Ai-Dong Zhang

  DOI：10.1021/jo5010185

  日期：2014.7.18

  A one-pot palladium-catalyzed synthesis of symmetrical and unsymmetrical diarylmethanones using acetophenone and aryl bromides as raw materials has been developed. In this reaction, acetophenone acts as a latent carbonyl donor and two pathways of palladium-catalyzed sequential coupling and aerobic oxidation are identified. The reaction is applicable to a spectrum of substrates and delivers the products

  已经开发了一种以苯乙酮和芳基溴化物为原料的一锅钯催化合成对称和不对称的二芳基甲酮。在该反应中，苯乙酮充当潜在的羰基供体，并鉴定了钯催化的顺序偶联和有氧氧化的两条途径。该反应适用于各种底物，并以中等至良好的产率提供产物。该方法可通过两步操作用于合成酮洛芬（一种非甾体类抗炎药），总产率为45％。
• Organocatalytic deprotonative functionalization of C(sp2)–H and C(sp3)–H bonds using in situ generated onium amide bases
  作者：Kiyofumi Inamoto、Hitomi Okawa、Hiroshi Taneda、Maomi Sato、Yutaro Hirono、Misato Yonemoto、Shoko Kikkawa、Yoshinori Kondo

  DOI：10.1039/c2cc35701a

  日期：——

  Onium amides, generated in situ from the combination of aminosilanes and onium fluorides (R(4)PF, R(4)NF), are employed for the first time as bases for catalytic deprotonative functionalization of C(sp(2))-H and activated C(sp(3))-H bonds under mild conditions.

  由氨基硅烷和氟化鎓（R（4）PF，R（4）NF）的组合就地生成的鎓酰胺首次用作C（sp（2））-H催化去质子功能化的基础和活化的C（sp（3））-H键在温和的条件下。
• A New Approach to 3-Substituted Indoles through Palladium-Catalyzed C-H Activation Followed by Intramolecular Amination Reaction of Enamines
  作者：Kiyofumi Inamoto、Takayuki Doi、Tadataka Saito、Kou Hiroya

  DOI：10.1055/s-0028-1087413

  日期：——

  Palladium-catalyzed C-H activation followed by intramolecular amination reaction of enamine compounds was achieved using a Pd(OAc)2 (10 mol%)/Cu(OAc)2 (100 mol%) catalyst system in DMSO. This work introduces an entirely new approach to 3-substituted indoles.

  使用Pd(OAc)2（10 mol%）/Cu(OAc)2（100 mol%）催化体系在DMSO中实现了钯催化的C-H活化，随后进行了烯胺化合物的分子内胺化反应。本工作介绍了一种全新的合成3-取代吲哚的方法。
• Synthesis of Symmetrical Diaryl Ketones by Cobalt-Catalyzed Reaction of Arylzinc Reagents with Ethyl Chloroformate
  作者：Alice Rérat、Christophe Michon、Francine Agbossou-Niedercorn、Corinne Gosmini

  DOI：10.1002/ejoc.201600738

  日期：2016.9

  Symmetrical diaryl ketones were prepared by a cross-coupling reaction between aryl bromides and ethyl chloroformate. This new method, which uses a catalyst composed of CoBr2 and a bipyridine ligand along with readily available starting materials, allows for the synthesis of a variety of symmetrical diaryl ketones in moderate to excellent yields (37–99 %) under mild conditions. This reaction, in which

  通过芳基溴化物和氯甲酸乙酯之间的交叉偶联反应制备对称二芳基酮。这种新方法使用由 CoBr2 和联吡啶配体组成的催化剂以及容易获得的起始材料，允许在温和条件下以中等至优异的产率 (37-99%) 合成各种对称的二芳基酮。在这种反应中，氯甲酸乙酯在钴和锌的存在下充当一氧化碳的替代物，代表了先前已知的二芳基甲酮合成方法的有趣替代方法。
• Spiro and dispiro 1,2,4-trioxolane antimalarials
  申请人：Medicines for Malaria Ventures MMV

  公开号：US20040039008A1

  公开（公告）日：2004-02-26

  A means and method for treating malaria, schistosomiasis, and cancer using a spiro or dispiro 1,2,4-trioxolane is described. The preferred 1,2,4-trioxolanes include a spiroadamantane group on one side of the trioxolane group, and a spirocyclohexyl on the other side of the trioxolane group, whereby the spirocyclohexyl ring is preferably substituted at the 4-position. In comparison to artemisinin semisynthetic derivatives, the compounds of this invention are structurally simple, easy to synthesize, non-toxic, and potent against malarial parasites.

  本发明涉及使用螺环或二螺环1,2,4-三噁烷治疗疟疾、血吸虫病和癌症的方法和手段。首选的1,2,4-三噁烷包括一个螺环戊烷基团位于三噁烷基团的一侧，以及一个螺环己基团位于三噁烷基团的另一侧，其中螺环己环在4位处优选被取代。与青蒿素半合成衍生物相比，本发明的化合物结构简单，易于合成，无毒，并且对疟原虫具有强效作用。