3,4,5-trimethoxy-α-hydroxyacetophenone | 87428-53-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,5-trimethoxy-α-hydroxyacetophenone
• 英文别名: 2-hydroxy-1-(3,4,5-trimethoxy-phenyl)-ethanone；2-Hydroxy-1-(3,4,5-trimethoxy-phenyl)-aethanon；α-Hydroxy-3,4,5-trimethoxy-acetophenon；3,4,5-Trimethoxy-α-hydroxy-acetophenon；2-Hydroxy-1-(3,4,5-trimethoxyphenyl)ethan-1-one；2-hydroxy-1-(3,4,5-trimethoxyphenyl)ethanone
• CAS: 87428-53-3
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: POXBLWNPHHZUJF-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  356.1±37.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4,5-trimethoxy-α-hydroxyacetophenone 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 11.0h， 生成 3-(4-Methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-oxazol-2-one
  参考文献：
  名称：

  Combretoxazolones: synthesis, cytotoxicity and antitumor activity

  摘要：

  Two series of combretoxazolones including 3,4-diaryloxazolones (6) and 4,5-diaryloxazolones (7) were synthesized and evaluated for cytotoxicity and antitumor activity. Both series showed strong cytotoxicities against a variety of tumor cell lines. Compound 6g exhibited a significant antitumor activity in BDF1 mice bearing B16 murine melanoma cells with inhibition rates of 67 and 61 % at 100 and 30 mg/kg/day, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00622-9
• 作为产物：
  描述：

  2-溴-1-(3,4,5-三甲氧基苯基)乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 3,4,5-trimethoxy-α-hydroxyacetophenone
  参考文献：
  名称：

  木质素模型化合物α-羟基苯乙酮合成吲哚和咔唑

  摘要：

  大多数木质素解聚产物都具有特定的官能团并具有多种反应性，因此具有作为合成高附加值产品的起始原料的巨大潜力。我们在本文中描述了使用氧化的木质素模型化合物 α-羟基苯乙酮作为合成吲哚或咔唑的起始材料并结合使用吡咯或吲哚作为对应试剂的有效策略。使用 Sc(OTf) 3进行反应作为生物基绿色溶剂甘油中的催化剂，获得了中等至优异的产率。在反应结束时，溶剂和催化剂都可以回收再利用。这里提出的新方法不仅为木质素降解产物的增值转化提供了一条生态高效的途径，而且还扩展了吲哚和咔唑衍生物的多样性，这在功能光电材料的开发中具有潜在的重要性。

  DOI：

  10.1039/d1gc04892a

文献信息

• Iron-TEMPO-Catalyzed Domino Aerobic Alcohol Oxidation/Oxidative Cross-Dehydrogenative Coupling for the Synthesis of α-Keto Amides
  作者：Surya Srinivas Kotha、Selvaraj Chandrasekar、Samrat Sahu、Govindasamy Sekar

  DOI：10.1002/ejoc.201402961

  日期：2014.11

  An iron-TEMPO-catalyzed (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyloxy), aerobic process was developed to synthesize α-keto amides. This reaction proceeds through a domino alcohol oxidation/oxidative cross-dehydrogenative coupling sequence, uses 2-hydroxyacetophenones and amines as the starting materials, and takes place under molecular oxygen, which makes the transformation highly efficient, practical

  开发了铁-TEMPO 催化（TEMPO = 2,2,6,6-四甲基-1-哌啶基氧基）的有氧工艺来合成 α-酮酰胺。该反应通过多米诺醇氧化/氧化交叉脱氢偶联序列进行，以2-羟基苯乙酮和胺类为起始原料，在分子氧下进行，使转化高效、实用且环保。
• NOVEL BENZAMIDE DERIVATIVE AND USE THEREOF
  申请人：VIVOZON, INC.

  公开号：US20140336378A1

  公开（公告）日：2014-11-13

  Disclosed are a novel benzamide derivative and pharmaceutical use thereof, and more particularly, a novel benzamide derivative having a structure of Formula 1 or pharmaceutically acceptable salts thereof, and a composition for prevention or treatment of pain or itching including the above material. The novel benzamide derivative and pharmaceutically acceptable salt thereof according to the present invention exhibit excellent pain-suppressive effect and, in particular, pain-suppressive effect in not only a neuropathic animal model but also other models such as a formalin model, and therefore, may be used in suppression of different pains such as nociceptive pain, chronic pain, etc. Further, since it was demonstrated that the present invention displays anti-pruritic efficacy even in an itching model, to which a mechanism and treatment concept established with respect to pain is applied, the present invention may also be effectively used in radical treatment of atopic dermatitis by applying the inventive product to an anti-pruritic composition in order to suppress an initial itching stage and treat symptoms thereof, thus preventing skin damage or inflammation after the scratching stage.

  揭示了一种新的苯甲酰胺衍生物及其药用，更具体地说，一种具有化学式1结构或其药用盐的新苯甲酰胺衍生物，以及包括上述材料的用于预防或治疗疼痛或瘙痒的组合物。根据本发明，所述新的苯甲酰胺衍生物及其药用盐表现出优异的镇痛效果，特别是在不仅神经病理动物模型中而且其他模型如福尔马林模型中表现出的镇痛效果，因此，可用于抑制不同类型的疼痛，如伤害性疼痛、慢性疼痛等。此外，由于证明了本发明在瘙痒模型中显示出抗瘙痒功效，应用于疼痛方面建立的机制和治疗概念，因此，本发明还可通过将创新产品应用于抗瘙痒组合物中，以抑制初始瘙痒阶段并治疗其症状，从而预防刮痒阶段后的皮肤损伤或炎症。
• Metal free synthesis of α-keto amides from 2-hydroxy acetophenones through domino alcohol oxidation–oxidative amidation reaction
  作者：Surya Srinivas Kotha、Govindasamy Sekar

  DOI：10.1016/j.tetlet.2015.09.053

  日期：2015.11

  An efficient method for the synthesis of α-keto amides using 2-iodoxybenzoic acid (IBX) promoted domino alcohol oxidation and oxidative amidation reaction sequence between 2-oxoalcohols and amines under metal-free conditions is developed. In this protocol, IBX is used as an oxidizing agent to synthesize the α-keto amides, which makes this methodology highly efficient, practical, and environmentally

  开发了一种在无金属条件下利用2-碘氧基苯甲酸（IBX）促进多米诺骨牌醇氧化和2-氧代醇与胺类之间的氧化酰胺化反应顺序合成α-酮酰胺的有效方法。在该协议中，IBX用作氧化剂来合成α-酮酰胺，这使该方法高效，实用且对环境无害。
• Copper-Mediated S_N2′ Allyl–Alkyl and Allyl–Boryl Couplings of Vinyl Cyclic Carbonates
  作者：Núria Miralles、José Enrique Gómez、Arjan W. Kleij、Elena Fernández

  DOI：10.1021/acs.orglett.7b02947

  日期：2017.11.17

  for the copper-catalyzed borylmethylation and borylation of vinyl cyclic carbonates through an SN2′ mechanism is reported. These singular reactions involve selective SN2′ allylic substitutions with concomitant ring opening of the cyclic carbonate and with extrusion of CO2 and formation of a useful hydroxyl functionality in a single step. The stereoselectivity of the homoallylic borylation and allylic

  报道了一种通过S N 2'机理进行铜催化的乙烯基环状碳酸酯的硼烷基甲基化和硼化的方法。这些奇异反应包括选择性的S N 2'烯丙基取代，伴随有环状碳酸酯的开环，以及CO 2的挤出和在单个步骤中形成有用的羟基官能团。可以控制均烯丙基硼化和烯丙基硼化过程的立体选择性，并且合成上有用的不饱和（E）-戊-2-烯-1,5-二醇和（E）-丁-2-烯-1,4-二醇是访问。
• Synthesis of new 2,4-diamino-7<i>H</i>-pyrrolo[2,3-<i>d</i>]pyrimidines via the Taylor ring transformation/ring annulation strategy
  作者：Andre Rosowsky、Hongning Fu、Sherry F. Queener

  DOI：10.1002/jhet.5570380526

  日期：2001.9

  2-aminofuran-3-carbonitriles, which upon heating with guanidine underwent ring transformation/ring annulation to produce 2,4-diamino-7H-pyrrolo[2,3-d]pyrimidines rather than 2,4-diaminofuro[2,3-d]pyrimidines. One of the target compounds obtained in this manner, 2,4-diamino-5-(3,4,5-trimethoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine (1d), may be viewed as a conformationally restricted analogue of trimethoprim

  选定的实施例合成了5-位具有苯基或苄基的2,4-二氨基-7 H-吡咯并[2,3- d ]嘧啶作为二氢叶酸还原酶（DHFR）的抑制剂，来自卡氏肺孢子虫和弓形虫，两个潜在的抑制剂与艾滋病和免疫系统其他疾病相关的威胁生命的机会病原体。将多聚甲醛与取代的苯甲醛或与苯乙醛进行醛醇缩合，制得在4位带有苯基或苄基的α-羟基酮。羟基酮与丙二腈的进一步反应得到2-氨基呋喃-3-甲腈，将其与胍一起加热进行环转化/环环化以生成2,4-二氨基-7 H-pyrrolo [2,3- d ]嘧啶，而不是2,4-二氨基呋喃[2,3- d ]嘧啶。以此方式获得的目标化合物之一，2,4-二氨基-5-（3,4,5-三甲氧基苯基）-7 H-吡咯并[2,3- d ]嘧啶（1d），可被视为构象上的甲氧苄啶的限制性类似物，一种抗微生物剂，广泛与磺胺类药物合用，用于治疗艾滋病患者的卡氏疟原虫和刚地弓形虫的机会性感染。化合物1D抑制卡氏肺囊虫和冈氏弓形虫DHFR用IC