2-<4-(ethoxycarbonyl)phenyl>pyridine N-oxide | 102676-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-<4-(ethoxycarbonyl)phenyl>pyridine N-oxide
• 英文别名: 2-(4-(ethoxycarbonyl)phenyl)pyridine N-oxide；2-(4-Ethoxycarbonylphenyl)pyridine N-oxide；2-(p-ethoxycarbonylphenyl)pyridine-N-oxide；ethyl 4-(1-oxidopyridin-1-ium-2-yl)benzoate
• CAS: 102676-38-0
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: NWHMYVOPXGENMI-UHFFFAOYSA-N

物化性质

• 沸点：
  468.5±28.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<4-(ethoxycarbonyl)phenyl>pyridine N-oxide 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氯化亚砜 、 氨 、 氢气 、 硫酸二甲酯 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 90.0 ℃ 、275.79 kPa 条件下， 反应 94.5h， 生成 法倔唑
  参考文献：
  名称：

  Fadrozole hydrochloride: a potent, selective, nonsteroidal inhibitor of aromatase for the treatment of estrogen-dependent disease

  摘要：

  A new class of potent, selective, nonsteroidal inhibitors of aromatase have been discovered. The most potent member of this series is fadrozole hydrochloride, CGS 16949 A, 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile monohydrochloride, 26a. In addition, the 6,7-dihydropyrrolo[1,2-c]imidazole (21a) and the 6,7,8,9-tetrahydroimidazo[1,5-a]azepine (21b) analogues were synthesized and evaluated. CGS 16949 A's ability to selectively inhibit aromatase (IC50 = 4.5nM) over other cytochrome P-450 enzymes and suppress estrogen production when administered orally make it a suitable candidate to test the potential of an aromatase inhibitor in estrogen-dependent diseases including breast cancer.

  DOI：

  10.1021/jm00106a038
• 作为产物：
  描述：

  ethyl 4-(2-pyridinyl)benzoate 在 过氧乙酸 作用下， 反应 3.0h， 生成 2-<4-(ethoxycarbonyl)phenyl>pyridine N-oxide
  参考文献：
  名称：

  Fadrozole hydrochloride: a potent, selective, nonsteroidal inhibitor of aromatase for the treatment of estrogen-dependent disease

  摘要：

  A new class of potent, selective, nonsteroidal inhibitors of aromatase have been discovered. The most potent member of this series is fadrozole hydrochloride, CGS 16949 A, 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile monohydrochloride, 26a. In addition, the 6,7-dihydropyrrolo[1,2-c]imidazole (21a) and the 6,7,8,9-tetrahydroimidazo[1,5-a]azepine (21b) analogues were synthesized and evaluated. CGS 16949 A's ability to selectively inhibit aromatase (IC50 = 4.5nM) over other cytochrome P-450 enzymes and suppress estrogen production when administered orally make it a suitable candidate to test the potential of an aromatase inhibitor in estrogen-dependent diseases including breast cancer.

  DOI：

  10.1021/jm00106a038

文献信息

• C–H Arylation of Heterocyclic <i>N</i>-Oxides Through <i>in Situ</i> Diazotisation Of Anilines without Added Promoters: A Green And Selective Coupling Process
  作者：Aymeric P. Colleville、Richard A. J. Horan、Sandrine Olazabal、Nicholas C. O. Tomkinson

  DOI：10.1021/acs.oprd.6b00117

  日期：2016.7.15

  A green and selective method for the generation of biaryl compounds through C–H arylation of heterocyclic N-oxides, in which the addition of ascorbic acid as a promoter is not required for either the generation of an aryldiazonium species or the subsequent arylation, is presented. Reaction conditions were optimized through multivariate data analysis, including orthogonal projections to latent structures

  提出了一种绿色的，选择性的方法，用于通过杂环N-氧化物的CH芳基化反应生成联芳基化合物，其中，芳基重氮化合物的生成或随后的芳基化反应均不需要添加抗坏血酸作为促进剂。 。通过多变量数据分析对反应条件进行了优化，包括对潜在结构的正交投影（OPLS）和实验设计（DoE）方法，从而进一步改善了可持续性，然后将其应用于一系列底物，以确定反应条件的范围和局限性。处理。使用原位研究反应提出了红外光谱学和一种机制，该机制解释了本研究和以前的研究中的可用数据。该反应还以克数进行，并进行了量热研究，以支持进一步扩大无启动子转化的规模。
• Coupling of Nitrogen Heteroaromatics and Alkanes without Transition Metals: A New Oxidative Cross-Coupling at CH/CH Bonds
  作者：Guojun Deng、Kirika Ueda、Shuichi Yanagisawa、Kenichiro Itami、Chao-Jun Li

  DOI：10.1002/chem.200801893

  日期：2009.1.2

  Look—no transition metal! Transition‐metal‐free systems for the direct cross‐coupling reactions of nitrogen heteroaromatics and alkanes are described. Under the influence of tBuOOtBu, pyridine N‐oxide derivatives react with alkanes to furnish the corresponding cross‐coupling products (alkylated nitrogen heterocycles) in good yields.

  看，没有过渡金属！描述了用于氮杂芳烃和烷烃直接交叉偶联反应的无过渡金属体系。在t BuOO t Bu的影响下，吡啶N-氧化物衍生物与烷烃反应，以高收率提供相应的交叉偶联产物（烷基化氮杂环）。
• Substituted imidazo[5-a]pyridine derviatives and other substituted
  申请人：Ciba-Geigy Corporation

  公开号：US05428160A1

  公开（公告）日：1995-06-27

  Disclosed are compounds of formula I ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl, substituted lower alkyl, nitro, halogen, free, etherified or esterified hydroxy, free, etherified, oxidised etherified or esterified mercapto, unsubstituted, mono- or disubstituted amino, ammonio, free or functionally modified sulfo, free or functionally modified formyl, C.sub.2 -C.sub.20 -acyl, cyano, free or functionally modified carboxy; and R.sub.2 represents hydrogen, lower alkyl, substituted lower alkyl, halogen; free, etherified or esterified hydroxy; free, etherified, oxidised etherified or esterified mercapto; free or functionally modified carboxy, or acyl; the 7,8-dihydro derivatives thereof; and compounds of the formula I* ##STR2## wherein n denotes 0, 1, 2, 3, or 4, and R.sub.1 and R.sub.2 are as defined above under formula I and salts thereof; e.g. as aromatase inhibitors; pharmaceutical compositions containing these compounds; the use of these compounds for the treatment of conditions responsive to e.g. aromatase inhibition in mammals; processes and intermediates for preparing these compounds.

  本发明涉及一种式子I的化合物：##STR1## 其中R.sub.1代表氢，低烷基，取代的低烷基，硝基，卤素，自由的，醚化或酯化的羟基，自由的，醚化，氧化醚化或酯化的巯基，未取代的，单取代或双取代的氨基，铵离子，自由的或功能修饰的磺酸基，自由的或功能修饰的甲酰基，C.sub.2-C.sub.20-酰基，氰基，自由的或功能修饰的羧基；R.sub.2代表氢，低烷基，取代的低烷基，卤素；自由的，醚化或酯化的羟基；自由的，醚化，氧化醚化或酯化的巯基；自由或功能修饰的羧基或酰基；其7,8-二氢衍生物；以及式I*的化合物：##STR2## 其中n表示0、1、2、3或4，而R.sub.1和R.sub.2如上述式I中所定义，并且它们的盐；例如作为芳香化酶抑制剂；含有这些化合物的制药组合物；这些化合物用于治疗响应于例如哺乳动物中的芳香化酶抑制的情况的用途；制备这些化合物的过程和中间体。
• Substituted imidazo[1,5-A]pyridine derivatives and other substituted
  申请人：Ciba-Geigy Corporation

  公开号：US04728645A1

  公开（公告）日：1988-03-01

  Disclosed are compounds of formula I ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl, substituted lower alkyl, nitro, halogen, free, etherified or esterified hydroxy, free, etherified, oxidized etherified or esterified mercapto, unsubstituted, mono- or disubstituted amino, ammonio, free or functionally modified sulfo, free or functionally modified formyl, C.sub.2 -C.sub.20 -acyl, cyano, free or functionally modified carboxy; and R.sub.2 represents hydrogen, lower alkyl, substituted lower alkyl, halogen; free, etherified or esterified hydroxy; free, etherified, oxidized etherified or esterified mercapto; free or functionally modified carboxy, or acyl; the 7,8-dihydro derivatives thereof; and compounds of the formula I* ##STR2## wherein n denotes 0, 1, 2, 3 or 4, and R.sub.1 and R.sub.2 are as defined above under formula I and salts thereof; e.g. as aromatase inhibitors; pharmaceutical compositions containing these compounds; the use of these compounds for the treatment of conditions responsive to e.g. aromatase inhibition in mammals; processes and intermediates for preparing these compounds.

  本发明揭示了式I的化合物：##STR1## 其中R.sub.1代表氢、低碳基、取代的低碳基、硝基、卤素、自由、醚化或酯化的羟基、自由、醚化、氧化醚化或酯化的巯基、未取代的、单取代或双取代的氨基、铵离子、自由或功能修饰的磺酸基、自由或功能修饰的甲酰基、C.sub.2-C.sub.20酰基、氰基、自由或功能修饰的羧基；R.sub.2代表氢、低碳基、取代的低碳基、卤素；自由、醚化或酯化的羟基；自由、醚化、氧化醚化或酯化的巯基；自由或功能修饰的羧基或酰基。其7,8-二氢衍生物；以及式I*的化合物：##STR2## 其中n表示0、1、2、3或4，R.sub.1和R.sub.2如上所述，以及其盐；例如作为芳香化酶抑制剂；含有这些化合物的制药组合物；使用这些化合物治疗对哺乳动物的芳香化酶抑制等反应性疾病的方法；制备这些化合物的过程和中间体。
• Ethylenediamine derivatives
  申请人：——

  公开号：US20040122063A1

  公开（公告）日：2004-06-24

  The invention relates a compound represented by the formula (1): Q 1 -Q 2 -C(═O)—N(R 1 )-Q 3 -N(R 2 )-T 1 -Q 4 ( 1 ) wherein R 1 and R 2 represent H or the like; Q 1 represents an aromatic ring, heterocyclic ring or the like; Q 2 represents a single bond, aromatic ring, heterocyclic ring or the like; Q 3 represents a group 1 or the like, Q 4 represents an aromatic ring, heterocyclic ring or the like; and T 1 represents —CO— or —SO 2 —, and a medicine which comprises the compound and is useful for thrombosis and embolism.

  本发明涉及一种由式（1）表示的化合物：Q1-Q2-C(═O)—N(R1)-Q3-N(R2)-T1-Q4(1)，其中R1和R2代表H或类似物；Q1代表芳香环，杂环或类似物；Q2代表单键，芳香环，杂环或类似物；Q3代表群1或类似物，Q4代表芳香环，杂环或类似物；T1代表—CO—或—SO2—，以及包含该化合物并对治疗血栓和栓塞有用的药物。