3-methoxy-(1-chloro-1-hydroxyimino-methyl)-benzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-methoxy-(1-chloro-1-hydroxyimino-methyl)-benzene
• 英文别名: N-Hydroxy-3-methoxybenzimidoylchloride；(1Z)-N-hydroxy-3-methoxybenzenecarboximidoyl chloride
• 化学式: C₈H₈ClNO₂
• 分子量: 185.61
• InChiKey: DEXRYCNUFWKXHS-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 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：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxy-(1-chloro-1-hydroxyimino-methyl)-benzene 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 3.0h， 生成 (5R)-3-(3-methoxyphenyl)-5-[(2S)-oxiran-2-yl]-4,5-dihydro-1,2-oxazole
  参考文献：
  名称：

  Conformationally restrained β-blocking oxime ethers. 2. Synthesis and β-adrenergic properties of diastereoisomeric anti and syn 2-(5′-(3′-aryl-substituted)isoxazolidinyl)-N-alkylethanolamines☆

  摘要：

  The diastereoisomeric 2-(5'-(3'-aryl)isoxazolidinyl) ethanolamines 1c-h-4c-h were synthesized as analogs of the corresponding P-blocking isoxazolines unsubstituted on the aromatic ring 1a-4a, with the aim of checking the effects on the adrenergic properties of the insertion of a methoxy group or a chlorine atom in the ortho, meta or para position of the phenyl ring of 1a-4a. The relative configurations of 1c-h-4c-h were assigned on the basis of their H-1-NMR spectral characteristics. The new isoxazolines 1c-h-4c-h were tested for their affinity towards beta(1)- and beta(2)-adrenoceptors by radioligand binding experiments; compounds showing the highest affinity were also assayed for their beta-adrenergic activity by functional tests on isolated preparations. The results showed that most of the new compounds (1c-h-4c-h) possess a slightly better capacity to interact with the beta-receptors, compared with the corresponding analogs unsubstituted on the phenyl ring (1a-4a), and that the substitution that leads to compounds with the best properties is the one with the chlorine atom. Quantum mechanical calculations carried out in order to look for possible correlations between the beta-adrenergic properties and the conformational and electronic characteristics induced by the presence of the substituents on the phenyl ring of compounds of types 1-4 do not suggest any reasonable explanation for the trend of the affinity data.

  DOI：

  10.1016/0223-5234(94)90108-2
• 作为产物：
  描述：

  (E)-3-methoxybenzaldoxime 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3-methoxy-(1-chloro-1-hydroxyimino-methyl)-benzene
  参考文献：
  名称：

  Conformationally restrained β-blocking oxime ethers. 2. Synthesis and β-adrenergic properties of diastereoisomeric anti and syn 2-(5′-(3′-aryl-substituted)isoxazolidinyl)-N-alkylethanolamines☆

  摘要：

  The diastereoisomeric 2-(5'-(3'-aryl)isoxazolidinyl) ethanolamines 1c-h-4c-h were synthesized as analogs of the corresponding P-blocking isoxazolines unsubstituted on the aromatic ring 1a-4a, with the aim of checking the effects on the adrenergic properties of the insertion of a methoxy group or a chlorine atom in the ortho, meta or para position of the phenyl ring of 1a-4a. The relative configurations of 1c-h-4c-h were assigned on the basis of their H-1-NMR spectral characteristics. The new isoxazolines 1c-h-4c-h were tested for their affinity towards beta(1)- and beta(2)-adrenoceptors by radioligand binding experiments; compounds showing the highest affinity were also assayed for their beta-adrenergic activity by functional tests on isolated preparations. The results showed that most of the new compounds (1c-h-4c-h) possess a slightly better capacity to interact with the beta-receptors, compared with the corresponding analogs unsubstituted on the phenyl ring (1a-4a), and that the substitution that leads to compounds with the best properties is the one with the chlorine atom. Quantum mechanical calculations carried out in order to look for possible correlations between the beta-adrenergic properties and the conformational and electronic characteristics induced by the presence of the substituents on the phenyl ring of compounds of types 1-4 do not suggest any reasonable explanation for the trend of the affinity data.

  DOI：

  10.1016/0223-5234(94)90108-2

文献信息

• Phosphinic acid-promoted addition reaction of isocyanides to (Z)-hydroximoyl chlorides: efficient synthesis of α-(hydroxyimino)amides
  作者：Takahiro Soeta、Suguru Takashita、Yoko Sakata、Yutaka Ukaji

  DOI：10.1039/c5ob02032h

  日期：——

  The reaction of (Z)-hydroximoyl chlorides with isocyanides promoted by phosphinic acid in the presence of triethylamine proceeds smoothly to afford α-(hydroxyimino)amides in good to high yields. Phosphinic acid plays an important role in effectively promoting the reaction. A wide range of (Z)-hydroximoyl chlorides and isocyanides were found to be suitable for this reaction.

  在三乙胺的存在下，（Z）-羟肟基氯与次膦酸促进的异氰酸酯的反应顺利进行，从而以高至高收率获得了α-（羟基亚氨基）酰胺。膦酸在有效促进反应中起重要作用。发现各种各样的（Z）-羟肟基氯和异氰酸酯适合于该反应。
• Efficient synthesis of 3,5-functionalized isoxazoles and isoxazolines<i>via</i>1,3-dipolar cycloaddition reactions of 1-propargyl- and 1-allylbenzotriazoles
  作者：Alan R. Katritzky、Martin A. C. Button、Sergey N. Denisenko

  DOI：10.1002/jhet.5570370616

  日期：2000.11

  3-Aryl-5-(benzotriazol-1-ylmethyl)- 10a-f and 3-p-methoxyphenyl-5-(α-benzotriazol-1-yl-α-ethoxymethyl)-isoxazole (13) were prepared in high yields by 1,3-dipolar cycloadditions of 1-propargyl-benzotriazole (5) and (α-ethoxypropargyl)benzotriazole (8), respectively, with nitrite oxides 3a-f (prepared in situ from benzohydroximoyl chlorides 2a-f). The benzotriazol-1-ylmethyl moiety was further elaborated

  通过以下方法高产率地制备了3-芳基-5-（苯并三唑-1-基甲基）-10a-f和3-对甲氧基苯基-5-（α-苯并三唑-1-基-α-乙氧基甲基）-异恶唑（13） 1-炔丙基-苯并三唑（5）和（α-乙氧基炔丙基）苯并三唑（8）的1，3-偶极环加成分别与亚硝酸盐氧化物3a-f（由苯并氧肟基氯化物2a-f原位制备）。通过顺序锂化并与醛，烷基卤化物和迈克尔受体反应，进一步精制了苯并三唑-1-基甲基部分。使用1-烯丙基苯并三唑（6）和1-（α-乙氧基烯丙基）苯并三唑（7）的相似的1，3-环加成以优异的产率得到3，5-取代的异恶唑啉11b，f和12。
• Pyrimidine derivatives as modulators of insulin-like growth factor-1 receptor (igf-i)
  申请人：Barlaam Bernard

  公开号：US20050054638A1

  公开（公告）日：2005-03-10

  The invention provides compounds of formula in which R 1 , R 2 , R 3 and R 4 have the meanings defined in the specification; processes for the preparation; pharmaceutical compositions containing them; a process for preparing the pharmaceutical compositions; and their use in therapy.

  该发明提供了公式中R1，R2，R3和R4具有规范中定义的含义的化合物；制备过程；包含它们的制药组合物；制备制药组合物的过程；以及它们在治疗中的使用。
• Substituted Spiro-Compounds And The Use Thereof For Producing Medicaments
  申请人：Frank Robert

  公开号：US20090275628A1

  公开（公告）日：2009-11-05

  The present invention relates to substituted spiro compounds, to processes for preparing them, to medicaments comprising these compounds and to the use of these compounds for producing medicaments.

  本发明涉及取代的螺环化合物，以及制备它们的过程，包括这些化合物的药物和使用这些化合物制备药物的用途。
• NOVEL COMPOUNDS
  申请人：Barlaam Bernard

  公开号：US20120095011A1

  公开（公告）日：2012-04-19

  The invention provides compounds of formula in which R 1 , R 2 , R 3 and R 4 have the meanings defined in the specification; processes for their preparation; pharmaceutical compositions containing them; a process for preparing the pharmaceutical compositions; and their use in therapy.

  本发明提供的化合物具有公式，其中R1，R2，R3和R4具有规范中定义的含义；制备它们的过程；包含它们的制药组合物；制备制药组合物的过程；以及它们在治疗中的使用。