N-hydroxy-3-(4-methoxyphenyl)propanamide | 67363-26-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-hydroxy-3-(4-methoxyphenyl)propanamide
• CAS: 67363-26-2
• 化学式: C₁₀H₁₃NO₃
• mdl: MFCD00033230
• 分子量: 195.218
• InChiKey: YPKVKEDNKOLIAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-hydroxy-3-(4-methoxyphenyl)propanamide 在 tetraethylammonium metaperiodate 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-(4-methoxyphenethyl)-N'-phenylurea
  参考文献：
  名称：

  Corrie, John E.T.; Kirby, Gordon W.; Sharma, Ram P., Journal of the Chemical Society. Perkin transactions I, 1982, # 7, p. 1571 - 1574

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基肉桂酸 在 氯化亚砜 、 palladium 10% on activated carbon 、 盐酸羟胺 、 氢气 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 17.5h， 生成 N-hydroxy-3-(4-methoxyphenyl)propanamide
  参考文献：
  名称：

  Chemical intervention in bacterial lignin degradation pathways: Development of selective inhibitors for intradiol and extradiol catechol dioxygenases

  摘要：

  Bacterial lignin degradation could be used to generate aromatic chemicals from the renewable resource lignin, provided that the breakdown pathways can be manipulated. In this study, selective inhibitors of enzymatic steps in bacterial degradation pathways were developed and tested for their effects upon lignin degradation. Screening of a collection of hydroxamic acid metallo-oxygenase inhibitors against two catechol dioxygenase enzymes, protocatechuate 3,4-dioxygenase (3,4-PCD) and 2,3-dihydroxyphenylpropionate 1,2-dioxygenase (MhpB), resulted in the identification of selective inhibitors D13 for 3,4-PCD (IC50 15 mu M) and D3 for MhpB (IC50 110 mu M). Application of D13 to Rhodococcus jostii RHA1 in minimal media containing ferulic acid led to the appearance of metabolic precursor protocatechuic acid at low concentration. Application of 1 mM disulfiram, an inhibitor of mammalian aldehyde dehydrogenase, to R. jostii RHA1, gave rise to 4-carboxymuconolactone on the beta-ketoadipate pathway, whereas in Pseudomonas fluorescens Pf-5 disulfiram treatment gave rise to a metabolite found to be glycine betaine aldehyde. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.05.002

文献信息

• Synthesis of Hydroxamic Acids by Using the Acid Labile O-2-Methylprenyl Protecting Group
  作者：Aigars Jirgensons、Anna Nikitjuka

  DOI：10.1055/s-0032-1317687

  日期：——

  Coupling of carboxylic acids with O-2-methylprenyl hydroxylamine provided O-protected hydroxamic acids, which could be deprotected by treatment with trifluoroacetic acid (TFA) in dichloromethane giving volatile by-products. Protected hydroxamic acids could be N-arylated or alkylated followed by deprotection to give N-substituted hydroxamic acids.

  羧酸与 O-2-甲基异戊二烯羟胺的偶联提供了 O-保护的异羟肟酸，可以通过在二氯甲烷中用三氟乙酸 (TFA) 处理来脱保护，产生挥发性副产物。受保护的异羟肟酸可以被 N-芳基化或烷基化，然后去保护以得到 N-取代的异羟肟酸。
• Revisiting Arene C(sp² )−H Amidation by Intramolecular Transfer of Iridium Nitrenoids: Evidence for a Spirocyclization Pathway
  作者：Yeongyu Hwang、Yoonsu Park、Yeong Bum Kim、Dongwook Kim、Sukbok Chang

  DOI：10.1002/anie.201808892

  日期：2018.10.8

  Two mechanistic pathways, that is, electrocyclization and electrophilic aromatic substitution, are operative in most intramolecular C−H amination reactions proceeding by metal nitrenoid catalysis. Reported here is an alternative mechanistic scaffold leading to benzofused δ‐lactams selectively. Integrated experimental and computational analysis revealed that the reaction proceeds by a key spirocyclization

  在通过金属类固醇催化进行的大多数分子内CH胺化反应中，有两种机理途径，即电环化和亲电子芳族取代。此处报道的是另一种机制性支架，可以选择性地导致苯并稠合的δ-内酰胺。综合的实验和计算分析表明，该反应通过关键的螺环化步骤进行，然后进行骨架重排。基于这种机理的见解，已开发出合成螺内酰胺的新途径。
• Synthesis of Lactams via Ir-Catalyzed C–H Amidation Involving Ir-Nitrene Intermediates
  作者：Jitian Liu、Wenjing Ye、Shuojin Wang、Junrong Zheng、Weiping Tang、Xiaoxun Li

  DOI：10.1021/acs.joc.0c00157

  日期：2020.3.20

  We have developed a divergent strategy for the synthesis of five- and six-membered lactams via either an amidation of sp3 C-H bonds or electrophilic substitution of arenes via Ir-nitrene intermediates. With the employment of a readily available iridium catalyst in dichloromethane or hexafluoro-2-propanol, a wide range of lactams were synthesized in good to excellent yields with high selectivity.

  我们已经开发了一种通过sp3 CH键的酰胺化或Ir-nitrene中间体亲电取代芳烃来合成五元和六元内酰胺的策略。通过在二氯甲烷或六氟-2-丙醇中使用易于获得的铱催化剂，以高至优异的产率和高选择性合成了多种内酰胺。
• Cross metathesis-mediated synthesis of hydroxamic acid derivatives
  作者：Shital Kumar Chattopadhyay、Subhankar Ghosh、Suman Sil

  DOI：10.3762/bjoc.14.285

  日期：——

  An alternative synthesis of α,ß-unsaturated hydroxamates via cross metathesis between a class-I olefin and N-benzyloxyacrylamide is reported. The reaction proceeds better in the presence of Grubbs' second generation catalyst within short time and in good yields (57-85%) with a range of substrates. Subsequent hydrogenation of each of the CM products delivers the title compounds in moderate to very good

  据报道，通过I类烯烃和N-苄氧基丙烯酰胺之间的交叉复分解，可以合成α，ß-不饱和异羟肟酸酯。在格拉布斯第二代催化剂的存在下，该反应在短时间内以多种底物在较高收率下（57-85％）更好地进行。随后，每种CM产品的氢化反应都会以中等至非常高的收率（70-89％）提供标题化合物。该协议的一个重要证明是生物活性环状肽Chap-31的异常氨基酸成分的制备。
• Ruthenium-Catalyzed Intramolecular Arene C(sp²)–H Amidation for Synthesis of 3,4-Dihydroquinolin-2(1<i>H</i>)-ones
  作者：Wenlong Sun、Cho-Hon Ling、Chi-Ming Au、Wing-Yiu Yu

  DOI：10.1021/acs.orglett.1c00781

  日期：2021.5.7

  2-dioxazol-5-ones to form dihydroquinoline-2-ones in excellent yields with excellent regioselectivity via a formal intramolecular arene C(sp2)–H amidation. The reactions of the 2- and 4-substituted aryl dioxazolones proceeds initially through spirolactamization via electrophilic amidation at the arene site, which is para or ortho to the substituent. A Hammett correlation study showed that the spirolactamization

  我们报道了[Ru（对-cymene）（l-脯氨酸）Cl]（[Ru1]）催化的1,4,2-二恶唑-5-酮环化反应形成二氢喹啉-2-酮，具有优异的产率和极好的区域选择性通过正式的分子内芳烃C（sp 2）–H酰胺化。2-和4-取代的芳基二恶唑酮的反应首先通过在芳烃位点上的亲电酰胺化的螺内酰胺化进行，该芳烃位点对取代基是对位的或邻位的。Hammett相关性研究表明，螺内酰胺化可能是由于对苯丙氨酸的亲电子亚硝基化合物攻击而发生的，其特征是-0.73的负ρ值。