1-(4-ethoxy-phenyl)-2,2-dihydroxy-ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-ethoxy-phenyl)-2,2-dihydroxy-ethanone
• 英文别名: 1-(4-Aethoxy-phenyl)-2,2-dihydroxy-aethanon；1-(4-Ethoxyphenyl)-2,2-dihydroxyethanone
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: ONGYLRVQXCDGKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  邻氨基苯甲醇 、 1-(4-ethoxy-phenyl)-2,2-dihydroxy-ethanone 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以50%的产率得到
  参考文献：
  名称：

  Acid-mediated four-component tandem cyclization: Access to multifused 1,3-benzoxazine frameworks

  摘要：

  An acid-mediated multicomponent reaction has been developed for the direct synthesis of multifused 1,3-benzoxazine derivatives from simple and readily available arylglyoxal monohydrates and 2-aminobenzyl alcohols under mild conditions. This novel protocol is proposed to proceed through intramolecular poly-heterocyclizations, thus leading to the formation of three new rings and six new chemical bonds, including four C-N and two C-O bonds. (C) 2018 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2018.10.059
• 作为产物：
  描述：

  4-乙氧基苯乙酮 在 碘 作用下， 以 二甲基亚砜 为溶剂， 生成 1-(4-ethoxy-phenyl)-2,2-dihydroxy-ethanone
  参考文献：
  名称：

  Metal-free dual sp3 C–H functionalization: I2-promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles

  摘要：

  An I-2-promoted sp(3) C-H functionalization has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available methyl ketones and benzylamines without any metal and peroxide catalyst. This domino oxidative cyclization process involves the cleavage of C H bond and the formation of C-N, C-O bonds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.072

文献信息

• Acid-Promoted Multicomponent Tandem Cyclization to Synthesize Fully Substituted Oxazoles via Robinson–Gabriel-Type Reaction
  作者：Rong-Rong Zhou、Qun Cai、Deng-Kui Li、Shi-Yi Zhuang、Yan-Dong Wu、An-Xin Wu

  DOI：10.1021/acs.joc.7b00763

  日期：2017.6.16

  An acid-promoted multicomponent reaction for the synthesis of diverse fully substituted oxazole derivatives from simple and readily available arylglyoxal monohydrates, nitriles, and various C-nucleophiles has been developed. This protocol features wide functional group diversity which is capable of installing 4-hydroxycoumarin, 2-naphthol, and 1,3-cyclohexanedione motifs to oxazoles. Mechanistic analysis

  已经开发了一种由酸促进的多组分反应，用于从简单易得的芳基乙二醛一水合物，腈和各种C-亲核试剂中合成各种完全取代的恶唑衍生物。该协议具有广泛的官能团多样性，能够将4-羟基香豆素，2-萘酚和1,3-环己二酮基序安装到恶唑类化合物上。机理分析表明，经典的Robinson-Gabriel反应是这种串联转化的关键步骤。
• Multicomponent Strategy to Pyrazolo[3,4-<i>e</i>]indolizine Derivatives under Microwave Irradiation
  作者：Jian-Jun Wang、Xian Feng、Zhan Xun、Da-Qing Shi、Zhi-Bin Huang

  DOI：10.1021/acs.joc.5b01314

  日期：2015.8.21

  A simple and efficient one-pot construction of pyrazolo[3,4-e]indolizine derivatives via a diethylamine-catalyzed three-component domino reaction of arylglyoxals, cyclic 1,3-diones, and 5-aminopyrazoles under microwave irradiation is described. In this one-pot transformation, seven bonds and two new rings are efficiently formed. This synthesis was confirmed to follow the group-assisted-purification

  描述了在微波辐射下通过芳基乙二醛，环状1,3-二酮和5-氨基吡唑的二乙胺催化的三组分多米诺反应，一种简单有效的一锅构建吡唑并[3,4- e ]吲哚嗪衍生物。在这种一锅转换中，有效地形成了七个键和两个新的环。确认该合成遵循组辅助纯化（GAP）化学过程，可以避免传统的重结晶或色谱纯化方法。
• A C–H Oxidation/Two-Fold Cyclization Approach to Imidazopyridoindole Scaffold under Mild Oxidizing Conditions
  作者：Jia-Chen Xiang、Zi-Xuan Wang、Yan Cheng、Jin-Tian Ma、Miao Wang、Bo-Cheng Tang、Yan-Dong Wu、An-Xin Wu

  DOI：10.1021/acs.joc.7b02448

  日期：2017.12.15

  An expeditious one-step synthesis of the imidazopyridoindole scaffold was achieved through the C–H oxidation/two-fold cyclization reaction of methyl ketone and tryptamine derivatives. Mild oxidizing conditions were employed to realize the efficient oxidation of C(sp3)–H bonds, while suppressing overoxidation of the intermediate and ensuring the cross-trapping of two in situ generated acylimine intermediates

  咪唑并吡啶并吲哚骨架的快速一步合成是通过甲乙酮和色胺的衍生物的C–H氧化/双重环化反应实现的。使用温和的氧化条件可实现C（sp 3）-H键的有效氧化，同时抑制中间体的过氧化并确保两个原位生成的acylimine中间体的交叉捕获。
• Design and Synthesis of 2-Acylbenzothiazoles via In Situ Cross-Trapping Strategy from Benzothiazoles with Aryl Ketones
  作者：Qinghe Gao、Xia Wu、Fengcheng Jia、Meicai Liu、Yanping Zhu、Qun Cai、Anxin Wu

  DOI：10.1021/jo302754c

  日期：2013.3.15

  An I-2/KOH synergistically promoted direct ring-opening aroylation of benzothiazoles with aryl ketones has been discovered. Aryl ketones were seen to act as carbonyl sources to construct 2-acylbenzothiazoles. This reaction could provide an example for the convergent integration of self-labor domino sequences based on an in situ cross-trapping strategy.
• Reprint of: Acid-mediated four-component tandem cyclization: Access to multifused 1,3-benzoxazine frameworks
  作者：Jungang Wang、Rongrong Zhou、Shiyi Zhuang、Anxin Wu

  DOI：10.1016/j.tet.2019.02.058

  日期：2019.3

  An acid-mediated multicomponent reaction has been developed for the direct synthesis of multifused 1,3-benzoxazine derivatives from simple and readily available arylglyoxal monohydrates and 2-aminobenzyl alcohols under mild conditions. This novel protocol is proposed to proceed through intramolecular poly-heterocyclizations, thus leading to the formation of three new rings and six new chemical bonds, including four C-N and two C-O bonds. (C) 2019 Published by Elsevier Ltd.