2-羟基-1-(4-硝基苯基)-1-乙酮 | 64611-67-2

• 物质功能分类: 医药中间体 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-羟基-1-(4-硝基苯基)-1-乙酮
• 中文别名: 2'-羟基-4-硝基苯乙酮
• 英文名称: 2-hydroxy-1-(4-nitrophenyl)ethanone
• 英文别名: α-hydroxy-p-nitroacetophenone
• CAS: 64611-67-2
• 化学式: C₈H₇NO₄
• 分子量: 181.148
• InChiKey: DRGHCHSDUDQWHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  140-143°C
• 沸点：
  338.4±17.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2914700090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温且干燥环境下使用。

反应信息

• 作为反应物：
  描述：

  2-羟基-1-(4-硝基苯基)-1-乙酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 4-硝基苯基-乙二醇
  参考文献：
  名称：

  Highly enantioselective deracemization of 1-phenyl-1,2-ethanediol and its derivatives by stereoinversion using Candida albicans in a one-pot process

  摘要：

  A very simple methodology was developed to transform racemic 1-(4-substitutedphenyl)-1,2-ethanediols using resting cells of Candida albicans CCT 0776 through a one-pot two-step process in which the (R)-stereoisomer was completely oxidized to the corresponding substituted-alpha-hydroxyacetophenones, which were completely reduced to produce (S)-1-(4-substitutedphenyl)-1,2-ethanediols in good isolated yield (60-85%) and with high enantiomeric excess (99% ee). The overall process corresponded to an enantioselective deracemization by stereoinversion of the (R)-enantiomer. The process was not achieved for other similar 1,2-diols using the same reaction conditions, which indicates a structural restriction of substrates by the active pocket of the enzymes of C. albicans involved in the stereoinversion process. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.08.018
• 作为产物：
  描述：

  4-硝基苯乙烯 在 叔丁基过氧化氢 、 碘 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 2-羟基-1-(4-硝基苯基)-1-乙酮
  参考文献：
  名称：

  钯催化的非对映选择性形式[5 + 3]环加成反应，制备融合有八元环的螺氧吲哚

  摘要：

  据报导，钯衍生的Isatin衍生的α-（三氟甲基）亚胺与芳基取代的乙烯基碳酸亚乙酯（VEC）的形式[5 + 3]的分子间环加成反应，提供了含三氟甲基的螺环新多烯与八元环稠合而成在温和的条件下，在布朗斯台德酸的存在下，以一锅法以高收率得到一个单一的非对映异构体。还使用手性膦配体实现了该反应的不对称形式，同时将得到的产物进一步转化以在氧化时得到螺氧基吲哚并吡咯烷衍生物。

  DOI：

  10.1021/acs.orglett.9b01748

文献信息

• Selective Debromination and α-Hydroxylation of α-Bromo Ketones Using Hantzsch Esters as Photoreductants
  作者：Jaehun Jung、Jun Kim、Gyurim Park、Youngmin You、Eun Jin Cho

  DOI：10.1002/adsc.201500734

  日期：2016.1.7

  Two transformations initiated by photoinduced one‐electron transfer to α‐bromo ketones have been demonstrated. Hantzsch esters donate one electron to α‐bromo ketones under photoirradiation, promoting reductive debromination. Subsequent reactions of the resulting radical species of the ketones with molecular oxygen and Hantzsch esters lead to α‐hydroxylation or debromination, respectively. The relative

  已经证明了由光诱导单电子转移到α-溴代酮引发的两种转变。Hantzsch酯在光辐照下向α-溴代酮提供一个电子，从而促进还原性脱溴作用。酮的自由基基团随后与分子氧和Hantzsch酯的反应分别导致α-羟基化或脱溴。这两个途径的相对优势很大程度上取决于反应条件，包括溶剂，O 2含量和汉茨sch酸酯的浓度。合成协议具有优势，因为它们需要环境友好的光源，分子氧和可见光。
• Spiro[indene-1,4′-oxa-zolidinones] Synthesis via Rh(III)-Catalyzed Coupling of 4-Phenyl-1,3-oxazol-2(3<i>H</i>)-ones with Alkynes: A Redox-Neutral Approach
  作者：Zhongsu Liu、Wenjing Zhang、Shan Guo、Jin Zhu

  DOI：10.1021/acs.joc.9b01804

  日期：2019.9.20

  C-H activation synthesis of heterocyclic spiro[4,4]nonanes has persistently witnessed the use of additional stoichiometric transition-metal oxidant when employing C═C bond as the spiro ring closure site. Herein, we have addressed the issue by reporting a redox-neutral strategy for spiro[indene-1,4'-oxa-zolidinones] synthesis via Rh(III)-catalyzed coupling of 4-phenyl-1,3-oxazol-2(3H)-ones with alkynes

  杂环金属螺[4,4]壬烷的过渡金属催化CH活化合成一直证明使用C═C键作为螺环封闭位点时会使用其他化学计量的过渡金属氧化剂。在这里，我们已经解决了这个问题，报告了通过Rh（III）催化的4-苯基-1,3-恶唑2（偶合）偶联合成螺[indene-1,4'-oxa-zolidinones]的氧化还原中性策略。 3H）-带有炔烃的化合物。该合成具有广泛的底物范围和高的区域特异性。
• Experimental Study on the Reaction Pathway of α-Haloacetophenones with NaOMe: Examination of Bifurcation Mechanism
  作者：Kohei Tagawa、Keita Sasagawa、Ken Wakisaka、Shunsuke Monjiyama、Mika Katayama、Hiroshi Yamataka

  DOI：10.1246/bcsj.20130253

  日期：2014.1.15

  The reaction of PhCOCH2Br and NaOMe in MeOH gave PhCOCH2OH as the major product and PhCOCH2OMe as the minor product. Substituent effects on the reactivity and product selectivity revealed that an electron-withdrawing substituent on the phenyl ring enhanced the overall reactivity and gave more alcohol than ether. It was indicated that the alcohol was formed via carbonyl addition-epoxidation, whereas the ether was formed by direct substitution. Substituent effects on the reaction rates, as well as the effects of NaOMe concentration on the rate and product ratio for both reactions of PhCOCH2Br and PhCOCH2Cl are in line with the mechanism that the alcohol and ether products were formed via two independent and concurrent routes, carbonyl addition and α-carbon attack, respectively, and thus the reaction mechanism could be different from the bifurcation mechanism previously predicted for the reaction of PhCOCH2Br by a simulation study in the gas phase.

  在甲醇中，PhCOCH2Br与NaOMe的反应主要生成PhCOCH2OH，次要生成PhCOCH2OMe。取代基对反应活性和产物选择性的影响表明，苯环上的吸电子取代基增强了整体反应活性，生成更多的醇而非醚。表明醇是通过羰基加成-环氧化反应生成的，而醚是通过直接取代反应生成的。取代基对反应速率的影响，以及NaOMe浓度对PhCOCH2Br和PhCOCH2Cl反应速率和产物比例的影响，均与以下机理一致：即醇和醚产物分别通过两个独立且并行的路径——羰基加成和α-碳攻击生成，因此反应机理可能不同于之前气体相模拟研究中预测的PhCOCH2Br反应的分支机制。
• Photocatalytic oxidation of primary and secondary benzylic alcohols to carbonyl compounds catalyzed by H3PW12O40/SiO2 under an O2 atmosphere
  作者：Saeid Farhadi、Mozhgan Afshari、Mansoureh Maleki、Zaynab Babazadeh

  DOI：10.1016/j.tetlet.2005.10.019

  日期：2005.12

  An efficient, selective and green procedure for the photocatalytic oxidation of primary and secondary benzylic alcohols to the corresponding aldehydes and ketones has been achieved using silica-encapsulated H3PW12O40 as a recyclable heterogeneous photocatalyst in acetonitrile under oxygen gas as the sole reoxidant of the catalyst.

  使用二氧化硅封装的H 3 PW 12 O 40作为乙腈中氧气可再循环的非均相光催化剂，在氧气作为唯一再氧化剂的条件下，已实现了将伯和仲苄醇光催化氧化为相应的醛和酮的高效，选择性和绿色程序催化剂。
• Kinase inhibitors
  申请人：——

  公开号：US20030225098A1

  公开（公告）日：2003-12-04

  The present application is directed to pyrazolopyrirnidine and furopyrimidine analogs of the formula (I) 1 wherein the substituents are as defined herein, which are useful as kinase inhibitors.

  本申请涉及式(I)的吡唑吡啶和呋喃嘧啶类似物，其中取代基如本文所定义，这些类似物可用作激酶抑制剂。