2-methyl-4-(pyridin-3-yl)but-3-yn-2-ol | 24202-80-0

• 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-methyl-4-(pyridin-3-yl)but-3-yn-2-ol
• 英文别名: 2-Methyl-4-(3-pyridinyl)-3-butyn-2-ol；2-methyl-4-pyridin-3-ylbut-3-yn-2-ol
• CAS: 24202-80-0
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: CZSZFVFDKRMCLP-UHFFFAOYSA-N

物化性质

• 熔点：
  55-56 °C
• 沸点：
  283.8±20.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-4-(pyridin-3-yl)but-3-yn-2-ol 在 copper(I) chloride 、 sodium hydroxide 、 氧气 作用下， 以 吡啶 、 甲苯 为溶剂， 反应 5.0h， 生成 1,4-bis(3-pyridyl)buta-1,3-diyne
  参考文献：
  名称：

  Synthesis of 1,4-di(n-pyridyl)buta-1,3-diyne and formation of charge-transfer complexes. X-Ray structure of 1,4-di(3-pyridyl)buta-1,3-diyne

  摘要：

  炔基吡啶通过两种不同的途径被成功制备：(a) 通过氯亚甲基(三苯基)膦叶立德与吡啶甲醛的Wittig反应，随后脱去氯化氢；(b) 由2-甲基-4-(吡啶基)丁-3-炔-2-醇中间体，通过脱去丙酮。1,4-双(吡啶基)丁-1,3-二炔通过氧化偶联反应以良好产率获得。报道了3-取代二聚物的X射线结构。得到了3-取代二炔的单-和二甲基盐，并形成了与四甲基对苯二胺(TMPD)的电荷转移络合物。

  DOI：

  10.1039/a605468d
• 作为产物：
  描述：

  2-吡啶基三氟甲磺酸酯 、 2-甲基-3-丁炔-2-醇 在 palladium on activated charcoal copper(l) iodide 、 potassium carbonate 、 三苯基膦 作用下， 生成 2-methyl-4-(pyridin-3-yl)but-3-yn-2-ol
  参考文献：
  名称：

  A Practical and Efficient Synthesis of the Selective Neuronal Acetylcholine-Gated Ion Channel Agonist (S)-(−)-5-Ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y)

  摘要：

  An efficient, high-yielding synthetic procedure for the preparation of the novel neuronal acetylcholine-gated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate [(S)-2, SIB-1508Y] is described. The key steps in the process include the lithium bis(trimethylsilyl)amide-mediated acylation of N-vinylpyrrolidinone with ethyl 5-bromonicotinate, a high-yielding sodium borohydride reduction of imine 5, and a new heteroaryl-alkyne cross-coupling protocol for the introduction of the ethyne moiety in (S)-2. The preparation of enantiomerically pure (S)-2 was accomplished via a combination of enantioselective reduction of imine 5 and crystallization of enantiomerically enriched 5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine (7) as the dibenzoyl-L-tartaric acid salt.

  DOI：

  10.1021/jo971572d

文献信息

• Sonogashira Reaction of Aryl and Heteroaryl Halides with Terminal Alkynes Catalyzed by a Highly Efficient and Recyclable Nanosized MCM-41 Anchored Palladium Bipyridyl Complex
  作者：Bo-Nan Lin、Shao-Hsien Huang、Wei-Yi Wu、Chung-Yuan Mou、Fu-Yu Tsai

  DOI：10.3390/molecules15129157

  日期：——

  A heterogeneous catalyst, nanosized MCM-41-Pd, was used to catalyze the Sonogashira coupling of aryl and heteroaryl halides with terminal alkynes in the presence of CuI and triphenylphosphine. The coupling products were obtained in high yields using low Pd loadings to 0.01 mol%, and the nanosized MCM-41-Pd catalyst was recovered by centrifugation of the reaction solution and re-used in further runs without significant loss of reactivity.

  使用纳米尺寸的MCM-41-Pd异质催化剂，在CuI和三苯基膦的存在下，催化芳基和杂芳基卤化物与末端炔烃的Sonogashira偶联反应。通过使用低至0.01摩尔%的Pd负载量，偶联产物以高产率获得，并且纳米尺寸的MCM-41-Pd催化剂通过离心反应溶液进行回收，并在进一步反应中重复使用，活性没有显著损失。
• Organocatalytic cycloaddition of carbonyl sulfide with propargylic alcohols to 1,3-oxathiolan-2-ones
  作者：Hui Zhou、Rui Zhang、Hui Zhang、Sen Mu、Xiao-Bing Lu

  DOI：10.1039/c9cy00062c

  日期：——

  adducts of a Lewis base (LB) were synthesized and first used to catalyze the cycloaddition of COS with propargylic alcohols under mild reaction conditions, selectively providing the functionalized 1,3-oxathiolane-2-ones with complete (Z) configuration selectivity. Among them, COS adducts of highly polarized olefins proved to be highly efficient organocatalysts for this transformation, with excellent yields

  合成了路易斯碱（LB）的一系列羰基硫（COS）加合物，并首先用于在温和的反应条件下催化COS与炔丙醇的环加成反应，选择性地提供官能化的1,3-氧杂硫杂环戊烷-2-酮（Z）构型选择性。其中，高极化烯烃的COS加合物被证明是该转化的高效有机催化剂，具有优异的收率和广泛的官能团相容性。通过同位素标记和化学计量实验进行的机理研究无可辩驳地表明，催化反应是通过LB-COS加合物介导的亲核加成机理。通过结合气体捕获（活化）和催化剂的功能，该策略为经济高效的COS还原工艺提供了方向。
• Imidazolyl and pyrazolyl ethyne compounds
  申请人：Cosford D. Nicholas

  公开号：US20050085523A1

  公开（公告）日：2005-04-21

  In accordance with the present invention, there is provided a novel class of heterocyclic compounds. Compounds of the invention contain a substituted, unsaturated five, six or seven membered heterocyclic ring that includes at least one nitrogen atom and at least one carbon atom. The ring additionally includes three, four or five atoms independently selected from carbon, nitrogen, sulfur and oxygen atoms. The heterocyclic ring has at least one substituent located at a ring position adjacent to a ring nitrogen atom. This mandatory substituent of the ring includes a moiety (B), linked to the heterocyclic ring via a carbon-carbon double bond, a carbon-carbon triple bond or an azo group. The mandatory substituent is positioned adjacent to the ring nitrogen atom. Invention compounds are capable of a wide variety of uses. For example heterocyclic compounds can act to modulate physiological processes by functioning as agonists and antagonists of receptors in the nervous system. Invention compounds may also act as insecticides, and as fungicides. Pharmaceutical compositions containing invention compounds also have wide utility.

  根据本发明，提供了一类新型的杂环化合物。该发明的化合物包含一个取代的、不饱和的五、六或七元杂环环，其中至少包含一个氮原子和至少一个碳原子。该环另外包括三、四或五个独立选择的碳、氮、硫和氧原子。杂环环在至少一个邻近环氮原子的环位置上具有至少一个取代基。该环的强制性取代基包括一个通过碳-碳双键、碳-碳三键或偶氮基与杂环环相连的基团（B）。强制性取代基位于环氮原子的邻近位置。本发明的化合物能够具有各种用途。例如，杂环化合物可以通过作为神经系统受体的激动剂和拮抗剂来调节生理过程。本发明的化合物也可以作为杀虫剂和杀菌剂。含有本发明化合物的药物组合物也具有广泛的用途。
• UC Pd: A New Form of Pd/C for Sonogashira Couplings
  作者：Christophe Duplais、Arnold J. Forman、Benjamin A. Baker、Bruce H. Lipshutz

  DOI：10.1002/chem.200902471

  日期：2010.3.15

  at 50 °C. It is also the only form of Pd/C that can be recycled. In side‐by‐side reactions with several commercially available forms of Pd/C, none compete successfully with UC Pd under standardized conditions. Physical data obtained from extensive surface analysis using TEM, XRD, XPS, and CO‐TPD measurements lead to an explanation behind the unique reactivity of this new recyclable form of Pd/C.

  对不同来源的 Pd/C 的筛选显示出具有高度可变的纳米颗粒尺寸和金属氧化态的试剂。通常，具有较高表面积的催化剂被认为可能更具反应性。在本文中，描述了一种新形式的 Pd/C，即“UC Pd”，它显示出包含更大的纳米颗粒，但它是商业上用于 Sonogashira 偶联反应的那些催化剂中反应性最强的催化剂。UC Pd 在没有铜助催化剂的情况下，在非常温和和“绿色”的条件下，在 50°C 下使用廉价的 95% EtOH 可有效发挥作用。它也是唯一可以回收的 Pd/C 形式。在与几种市售形式的 Pd/C 的并行反应中，在标准化条件下，没有一种能与 UC Pd 成功竞争。使用 TEM、XRD、XPS、从广泛的表面分析中获得的物理数据，
• Pyridazine, pyrimidine and pyrazine ethyne compounds
  申请人：Cosford D. Nicholas

  公开号：US20050043307A1

  公开（公告）日：2005-02-24

  In accordance with the present invention, there is provided a novel class of heterocyclic compounds. Compounds of the invention contain a substituted, unsaturated five, six or seven membered heterocyclic ring that includes at least one nitrogen atom and at least one carbon atom. The ring additionally includes three, four or five atoms independently selected from carbon, nitrogen, sulfur and oxygen atoms. The heterocyclic ring has at least one substituent located at a ring position adjacent to a ring nitrogen atom. This mandatory substituent of the ring includes a moiety (B), linked to the heterocyclic ring via a carbon-carbon double bond, a carbon-carbon triple bond or an azo group. The mandatory substituent is positioned adjacent to the ring nitrogen atom. Invention compounds are capable of a wide variety of uses. For example heterocyclic compounds can act to modulate physiological processes by functioning as agonists and antagonists of receptors in the nervous system. Invention compounds may also act as insecticides, and as fungicides. Pharmaceutical compositions containing invention compounds also have wide utility.

  根据本发明，提供了一类新型的杂环化合物。该发明的化合物包含一个取代的、不饱和的五、六或七元杂环环，其中至少包含一个氮原子和至少一个碳原子。该环另外包括三、四或五个独立选择的碳、氮、硫和氧原子。杂环环至少有一个取代基位于邻近环氮原子的环位置。该环的强制性取代基包括一个通过碳-碳双键、碳-碳三键或偶氮基与杂环环连接的基团（B）。强制性取代基位于环氮原子的邻近位置。本发明的化合物能够广泛用于各种用途。例如，杂环化合物可以通过作为神经系统受体的激动剂和拮抗剂来调节生理过程。本发明的化合物也可以作为杀虫剂和杀菌剂。含有本发明化合物的药物组合物也具有广泛的用途。

表征谱图