[3-(氨基氧基)-1-丙炔-1-基]苯 | 149649-90-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [3-(氨基氧基)-1-丙炔-1-基]苯
• 英文名称: O-(3-phenyl-2-propynyl)hydroxylamine
• 英文别名: O-(3-phenylprop-2-ynyl)hydroxylamine
• CAS: 149649-90-1
• 化学式: C₉H₉NO
• 分子量: 147.177
• InChiKey: ZHFXDAQXMNYCTI-UHFFFAOYSA-N

物化性质

• 沸点：
  281.0±23.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [3-(氨基氧基)-1-丙炔-1-基]苯 在 碳酸氢钠 、 sodium carbonate 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 17.0h， 生成 benzyl 2,5-dihydro-3-phenyl-4-(2-thienyl)-2H-isoxazole-2-carboxylate
  参考文献：
  名称：

  Iodocyclization of Hydroxylamine Derivatives Based on the Control of Oxidative Aromatization Leading to 2,5-Dihydroisoxazoles and Isoxazoles

  摘要：

  An efficient method for the synthesis of 2,5-dihydroisoxazoles and isoxazoles using iodocyclization of N-alkoxycarbonyl O-propargylic hydroxylamines has been developed. 2,5-Dihydro-4-iodoisoxazole underwent the cross-coupling reactions without aromatization to afford polyfunctionalized 2,5-dihydroisoxazoles. This process was applied to the preparation of valdecoxib and its 2,5-dihydro-derivative.

  DOI：

  10.1021/jo200407b
• 作为产物：
  描述：

  3-苯基-2-丙炔-1-醇 在 三苯基膦 、 甲基肼 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [3-(氨基氧基)-1-丙炔-1-基]苯
  参考文献：
  名称：

  m1-选择性毒蕈碱激动剂的设计与合成：（R）-（-）-（Z）-1-氮杂双环[2.2.1]庚-3-酮，O-（3-（3'-甲氧基苯基）-2-丙炔基肟肟马来酸酯（CI-1017），一种功能性m1选择性毒蕈碱激动剂。

  摘要：

  一系列（Z）-（+/-）-1-氮杂双环[2.2。]的合成和SAR。1]庚烷-3-酮，O-（3-芳基-2-丙炔基）肟被描述。重点介绍了24Z（PD 142505）及其对映异构体的生物化学和药理作用。24Z在功能上是m1选择性毒蕈碱激动剂。功效和m1选择性存在于R对映异构体（R）-24Z（CI-1017）中。

  DOI：

  10.1021/jm960683m

文献信息

• In vitro and in vivo evaluation of the subtype-selective muscarinic agonist PD 151832
  作者：J. Jaen、S. Barrett、M. Brann、M. Callahan、R. Davis、P. Doyle、D. Eubanks、D. Lauffer、L. Lauffer、W. Lipinski、D. Moreland、C. Nelson、C. Raby、R. Schwarz、C. Spencer、H. Tecle

  DOI：10.1016/0024-3205(95)00019-3

  日期：1995.2

  PD 151832 is a potent partial muscarinic agonist that displays a high level of functional selectivity for the muscarinic m1 receptor subtype, as evidenced by its selective stimulation of PI turnover and cellular metabolic activity in transfected Hm1-CHO cells at concentrations that produce minimal stimulation of other cloned human muscarinic receptors. PD 151832 enhanced the amplification of Hm1-transfected

  PD 151832是一种强效的部分毒蕈碱激动剂，对毒蕈碱m1受体亚型显示出高水平的功能选择性，这一点可通过其对PI转染的选择性刺激和对Hm1-CHO细胞的细胞代谢活性的选择性刺激来证明，其浓度对其他药物几乎没有刺激克隆的人毒蕈碱受体。PD 151832增强了Hm1转染的NIH-3T3细胞的扩增，其浓度低于在Hm2或Hm3转染的细胞中产生类似作用所需的浓度。PD 151832的功能性m1选择性与其对小鼠水迷宫性能的改善相一致，其剂量远低于产生周围副交感神经副作用所需的剂量。
• FUNGICIDAL OXIMES AND HYDRAZONES
  申请人：Hanagan Mary Ann

  公开号：US20130030002A1

  公开（公告）日：2013-01-31

  Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, wherein E, X, G, W 2 and Z are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention. Also disclosed are compounds of Formula 1A including all stereoisomers, N-oxides, and salts thereof, wherein E, X, G and Z 1 are as defined in the disclosure. Also disclosed is the use of the compounds of Formula 1A as intermediates for preparing compounds of Formula 1.

  本发明涉及公式1的化合物，包括所有立体异构体、N-氧化物和其盐，其中E、X、G、W2和Z如本公开说明书中所定义。还涉及含有公式1化合物的组合物以及控制由真菌病原体引起的植物病害的方法，包括施用本发明化合物或组合物的有效量。还涉及公式1A的化合物，包括所有立体异构体、N-氧化物和其盐，其中E、X、G和Z1如本公开说明书中所定义。还涉及将公式1A的化合物用作制备公式1化合物的中间体的用途。
• Synthesis of Azetidine Nitrones and Exomethylene Oxazolines through a Copper(I)-Catalyzed 2,3-Rearrangement and 4π-Electrocyclization Cascade Strategy
  作者：Jin-Qi Zhang、Pei-Wen Qiu、Cui Liang、Dong-Liang Mo

  DOI：10.1021/acs.orglett.2c03156

  日期：2022.10.28

  A variety of azetidine nitrones are prepared in moderate to good yields through copper(I) combined with 2-aminopyridine to catalyze skeletal rearrangement of O-propargylic oximes. Mechanistic studies reveal that the reaction undergoes a copper(I)-catalyzed tandem [2,3]-rearrangement, 4π-electrocyclization, ring opening, and recyclization over four steps in one pot. Substituents at the terminus of alkyne

  通过铜 (I) 与 2-氨基吡啶结合催化O-炔丙基肟的骨架重排，以中等到良好的产率制备了多种氮杂环丁烷硝酮。机理研究表明，该反应在一锅中经历了铜 (I) 催化的串联 [2,3]-重排、4π-电环化、开环和再循环四个步骤。炔烃和肟部分末端的取代基分别对氮杂环丁烷硝酮和外亚甲基恶唑啉的形成有显着影响。此外，所获得的氮杂环丁烷硝酮可以很容易地参与与炔酸酯的[3 + 2]环加成反应，并以溴[2.2]-对环芳烷为原料，通过五步合成了[2.2]-对环芳烷衍生的氮杂环丁烷硝酮，产率为45%。
• Synthesis and Biological Characterization of 1,4,5,6-Tetrahydropyrimidine and 2-Amino-3,4,5,6-tetrahydropyridine Derivatives as Selective m1 Agonists
  作者：William S. Messer,、Yahaya F. Abuh、Yang Liu、Sumudra Periyasamy、Dan O. Ngur、Michael A. N. Edgar、Afif A. El-Assadi、Sbeih、Philip G. Dunbar、Scott Roknich、Taikyun Rho、Zheng Fang、Babatunde Ojo、Hao Zhang、James J. Huzl、Peter I. Nagy

  DOI：10.1021/jm960467d

  日期：1997.4.1

  Previous studies identified several novel tetrahydropyrimidine derivatives exhibiting muscarinic agonist activity in rat brain. Such compounds might be useful in treating cognitive and memory deficits associated with low acetylcholine levels, as found in Alzheimer's disease. To determine the molecular features of ligands important for binding and activity at muscarinic receptor subtypes, the series of tetrahydropyrimidines was extended. Several active compounds were examined further for functional selectivity through biochemical studies of muscarinic receptor activity using receptor subtypes expressed in cell lines. Several amidine derivatives displayed high efficacy at m1 receptors and lower activity at m3 receptors coupled to phosphoinositide (PI) metabolism in A9 L cells. Four ligands, including 1b, 1f, 2b, and 7b, exhibited marked functional selectivity for m1 vs m3 receptors. Compound 1f also exhibited low activity at m2 receptors coupled to the inhibition of adenylyl cyclase in A9 L cells. Molecular modeling studies also were initiated to help understand the nature of the interaction of muscarinic agonists with the m1 receptor using a nine amino model of the m1 receptor. Several important interactions were identified, including interactions between the ester moiety and Thr192. Additional interactions were found for oxadiazoles and alkynyl derivatives with Asn382, suggesting that enhanced potency and selectivity may be achieved by maximizing interactions with Asp105, Thr192, and Asn382. Taken together, the data indicate that several amidine derivatives display functional selectivity for m1 muscarinic receptors, warranting further evaluation as therapeutic agents for the treatment of Alzheimer's disease. In addition, several amino acid residues were identified as potential binding sites for m1 agonists. These data may be useful in directing efforts to develop even more selective m1 agonists.
• Dérivés d'indénoindolones, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：Les Laboratoires Servier

  公开号：EP1266887B1

  公开（公告）日：2005-08-17