3-(4-吡啶基)-2-丙炔-1-醇 | 93524-95-9

• 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
• 中文名称: 3-(4-吡啶基)-2-丙炔-1-醇
• 英文名称: 3-(4-pyridinyl)-2-propyn-1-ol
• 英文别名: 3-(pyridin-4-yl)prop-2-yn-1-ol；3-(4-Pyridyl)-2-propyn-1-ol；3-pyridin-4-ylprop-2-yn-1-ol
• CAS: 93524-95-9
• 化学式: C₈H₇NO
• 分子量: 133.15
• InChiKey: QYFHTILWEGBMKR-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  273.6±20.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090
• 储存条件：
  室温且干燥

反应信息

• 作为反应物：
  描述：

  3-(4-吡啶基)-2-丙炔-1-醇 在 palladium on activated charcoal 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 4-吡啶丙醇
  参考文献：
  名称：

  The insulin secretory action of novel polycyclic guanidines: Discovery through open innovation phenotypic screening, and exploration of structure–activity relationships

  摘要：

  We report the discovery of the glucose-dependent insulin secretogogue activity of a novel class of polycyclic guanidines through phenotypic screening as part of the Lilly Open Innovation Drug Discovery platform. Three compounds from the University of California, Irvine, 1-3, having the 3-arylhexahydropyrrolo[1,2-c] pyrimidin-1-amine scaffold acted as insulin secretagogues under high, but not low, glucose conditions. Exploration of the structure-activity relationship around the scaffold demonstrated the key role of the guanidine moiety, as well as the importance of two lipophilic regions, and led to the identification of 9h, which stimulated insulin secretion in isolated rat pancreatic islets in a glucose-dependent manner. (C) 2014 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.01.021
• 作为产物：
  描述：

  4-碘吡啶 、 2-丙炔-1-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 3-(4-吡啶基)-2-丙炔-1-醇
  参考文献：
  名称：

  使用空气稳定的贱金属催化剂将炔烃化学选择性氢化为（Z）烯烃。

  摘要：

  已经实现了使用空气稳定且易于获得的锰催化剂对炔烃的高度选择性加氢。该反应在温和的反应条件下进行并能耐受各种官能团，从而以高收率得到（Z）-烯烃和烯丙基醇。力学实验表明，该反应通过涉及金属-配体协同作用的双功能活化来进行。

  DOI：

  10.1021/acs.orglett.0c01783

文献信息

• [EN] RET INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF<br/>[FR] INHIBITEURS DE RET, COMPOSITIONS PHARMACEUTIQUES ET UTILISATIONS ASSOCIÉES
  申请人：SUNSHINE LAKE PHARMA CO LTD

  公开号：WO2020114494A1

  公开（公告）日：2020-06-11

  Provided herein are a RET inhibitor, a pharmaceutical composition thereof and uses thereof. In particular, provided is a compound having Formula (I) or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof. Provided is a pharmaceutical composition comprising the compound, and uses of the compound and pharmaceutical composition thereof for the preparation of a medicament, in particular for treatment and prevention of RET-related diseases and conditions, including cancer, irritable bowel syndrome, and/or pain associated with irritable bowel syndrome.

  本文提供了一种RET抑制剂，其药物组合物及用途。具体而言，提供了具有化学式（I）或其立体异构体、几何异构体、互变异构体、N-氧化物、溶剂合物、代谢物、药用可接受的盐或其前药的化合物。提供了包含该化合物的药物组合物，并提供了该化合物及其药物组合物的用途，用于制备药物，特别是用于治疗和预防与RET相关的疾病和症状，包括癌症、肠易激综合征以及与肠易激综合征相关的疼痛。
• Sonogashira cross-coupling reactions with heteroaryl halides in the presence of a tetraphosphine–palladium catalyst
  作者：Marie Feuerstein、Henri Doucet、Maurice Santelli

  DOI：10.1016/j.tetlet.2005.01.044

  日期：2005.3

  Heteroaryl halides undergoes cross-couplings with alkynes in good yields in the presence of [PdCl(C3H5)]2/cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as catalyst. A variety of heteroaryl halides such as pyridines, quinolines, a pyrimidine, an indole, a thiophene, or a thiazole have been used successfully. The reaction also tolerates several alkynes such as phenylacetylene and

  在[PdCl（C 3 H 5）] 2 /顺式，顺式，顺式-1,2,3,4-四（二苯基膦甲基）环戊烷的存在下，杂芳基卤化物与炔烃进行交叉偶联，收率很高。已经成功地使用了各种杂芳基卤化物，例如吡啶，喹啉，嘧啶，吲哚，噻吩或噻唑。该反应还可以耐受几种炔烃，例如苯乙炔和一系列烷-1-炔醇。此外，该催化剂可在低负荷下与某些底物一起使用。
• Preparation of monoalkylpiperidines via the mild hydrogenation of monoalkynylpyridines
  作者：Toyonobu Usuki、Akira Komatsu

  DOI：10.1016/j.tetlet.2017.06.022

  日期：2017.7

  Monoalkynylpyridines were prepared via a Sonogashira cross-coupling reaction between monoiodopyridines and alkynes. Mild hydrogenation of the obtained monoalkynylpyridines was then conducted to produce the corresponding monoalkylpiperidines in moderate to excellent yields. The hydrogenation reaction was carried out under H2 (1 atm) in the presence of 10 wt% Pd/C (5 eq) in either AcOH or MeOH at room

  通过单碘吡啶和炔之间的Sonogashira交叉偶联反应制备单炔吡啶。然后进行所获得的单炔基吡啶的轻度氢化，以中等至优异的产率产生相应的单烷基哌啶。氢化反应是在H 2（1 atm）下，在10 wt％Pd / C（5 eq）存在下于室温在AcOH或MeOH中进行的。因此，本温和的方法对于快速和容易地制备单烷基哌啶是有用的。
• On the regioselectivity of Pd-catalyzed additions of organoboronic acids to unsymmetrical alkynes
  作者：Nakjoon Kim、Ki Seong Kim、Aruna Kumar Gupta、Chang Ho Oh

  DOI：10.1039/b316446b

  日期：——

  The Pd-catalyzed reaction of unsymmetrical alkynes with organoboronic acids gave a mixture of products and, whose ratios were controlled by the electronic as well as steric effects of the substrates.

  Pd催化的不对称炔烃与有机硼酸的反应生成了产物混合物，其比率受底物的电子和空间效应控制。
• Photochemical synthesis and properties of axially chiral naphthylpyridines
  作者：Pablo Wessig、Charlotte Pick

  DOI：10.1016/j.jphotochem.2011.06.006

  日期：2011.7

  Five alkynyl pyridines were prepared and cyclized to naphthylpyridines as the main products in the course of a Photo-Dehydro-Diels-Alder reaction. Four of the final products are axially chiral and the determination of the rotational barrier by DFT calculations, dynamic NMR and HPLC experiments is demonstrated.

  制备了五个炔基吡啶，并在光-脱氢-狄尔斯-阿尔德反应过程中环化成萘啶作为主要产物。最终产品中有四个是轴向手性的，并且通过DFT计算，动态NMR和HPLC实验证明了旋转势垒的确定。