4-2-吡啶-2-甲基-3-丁基-2-醇 | 29767-97-3

• 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: 4-2-吡啶-2-甲基-3-丁基-2-醇
• 中文别名: 4-(2-吡啶基)-2-甲基-3-丁炔-2-醇
• 英文名称: 2-methyl-4-(pyrid-2-yl)but-3-yn-2-ol
• 英文别名: 2-methyl-4-(pyridin-2-yl)but-3-yn-2-ol；2-methyl-4-(2'-pyridyl)-3-butyn-2-ol；4-(2-pyridyl)-2-methyl-3-butyn-2-ol；2-methyl-4-pyridin-2-ylbut-3-yn-2-ol
• CAS: 29767-97-3
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: YBUWIVMOMHEALF-UHFFFAOYSA-N

物化性质

• 熔点：
  82-84°C
• 沸点：
  120°C 1,5mm
• 密度：
  1.10±0.1 g/cm3(Predicted)
• 闪点：
  120°C/1.5mm
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，未有已知危险反应。请避免与氧化物接触。

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

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2933399090
• 储存条件：
  请将贮藏器密封，并存放在阴凉、干燥处。同时，确保工作环境具有良好的通风或排气设施。

反应信息

• 作为反应物：
  描述：

  4-2-吡啶-2-甲基-3-丁基-2-醇 在 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以84%的产率得到2-乙炔基吡啶
  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-氯吡啶 、 2-甲基-3-丁炔-2-醇 在 palladium on activated charcoal copper(l) iodide 、 二异丙胺 、 三苯基膦 作用下， 以 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 24.0h， 以51%的产率得到4-2-吡啶-2-甲基-3-丁基-2-醇
  参考文献：
  名称：

  Sonogashira Coupling of Aryl Halides Catalyzed by Palladium on Charcoal

  摘要：

  With the proper choice of solvent, palladium on charcoal acts as an efficient catalyst in the Sonogashira cross-coupling reaction of aryl bromides. The catalytically active species in the process is probably palladium, which leaches into the solution but returns onto the surface of the charcoal at the end of the reaction.

  DOI：

  10.1021/jo034149f

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。
• Fused Selenazolinium Salt Derivatives with a Se-N⁺Bond: Preparation and Properties
  作者：Pavel Arsenyan、Jelena Vasiljeva、Sergey Belyakov、Edvards Liepinsh、Marina Petrova

  DOI：10.1002/ejoc.201500582

  日期：2015.9

  Convenient methods for the preparation of stable, fused selenazolinium salt systems with a Se–N+ bond have been developed. The mechanism for the formation of the selenazole cycle was investigated in detail by conducting multinuclear NMR experiments. The ability of these compounds to form stable inner salts was demonstrated. We have shown the glutathione peroxidase (GPx) like properties of selenazolopyridinium

  已经开发了用于制备稳定的、具有 Se-N+ 键的稠合硒唑啉盐体系的便捷方法。通过进行多核核磁共振实验，详细研究了硒唑循环的形成机制。证明了这些化合物形成稳定内盐的能力。我们已经通过氧化含硫的天然氨基酸以及芳香醛和杂芳香醛，展示了硒唑并吡啶鎓盐的类似谷胱甘肽过氧化物酶 (GPx) 的特性。大多数化合物的分子结构已通过 X 射线衍射研究证实。
• Syntheses and quadratic hyperpolarizabilities of some (pyridylalkynyl)metal complexes: crystal structures of [Ni{2-(CC)C5H3NNO2-5}(PPh3)(η-C5H5)], [Au{2-(CC)C5H3NNO2-5}(PPh3)] and [Au{2-(CC)C5H4N}(PPh3)] ‡
  作者：Raina H. Naulty、Marie P. Cifuentes、Mark G. Humphrey、Stephan Houbrechts、Carlo Boutton、André Persoons、Graham A. Heath、David C. R. Hockless、Barry Luther-Davies、Marek Samoc

  DOI：10.1039/a702249b

  日期：——

  The complexes [Ru2-(CC)C5H3NR-5}(PPh3)2(η-C5H5)] (R = NO2 1 or H 2), [Ni2-(CC)C5H3NR-5}(PPh3)(η-C5H5)] (R = NO2 3 or H 4) and [Au2-(CC)C5H3NR-5}L] (L = PPh3, R = NO2 5 or H 6; L = PMe3, R = NO2 7) have been synthesized and 3, 5 and 6 structurally characterized; no significant increase in quinoidal vinylidene contribution to the acetylide ground-state structure is apparent on progression from structurally characterized phenylacetylide complexes to the new pyridylacetylide complexes, or upon replacement of 5-H by 5-NO2 in progressing from 6 to 5. The molecular quadratic optical non-linearities of 1–7 have been determined by hyper-Rayleigh scattering (HRS). The HRS measurements at 1064 nm are consistent with an increase in β upon replacement of phenyl by an N-heterocyclic ring (replacing a nitrophenylacetylide by a nitropyridylacetylide ligand) for the ruthenium and gold systems, but with no change for the nickel complexes, and with an increase in non-linearity upon replacement of PMe3 by PPh3 in progressing from 7 to 5. The bulk second-order susceptibilities of the series have been determined by Kurtz powder measurements at 1064 nm, with the only significant response (about eight times that of urea) being that of 3; this complex was the only one of the three structurally characterized to pack non-centrosymmetrically in the crystal lattice. Electrochemical data for 1–4 have been obtained; comparison to analogous nitrophenylacetlylide complexes reveals that replacing nitrophenylacetylide by nitropyridylacetylide leads to a significant increase in MII/III oxidation potential for the ruthenium complexes, but to no change for the nickel examples. The parameter E°MII/III – E°NO2/NO2– was evaluated for 1–4, results for M = Ru vs. Ni being consistent with experimentally determined non-linearities, i.e. smaller ΔE° and larger non-linearities for ruthenium vs. nickel.

  复合物 [Ru2-(CC)C5H3NR-5}(PPh3)2(η-C5H5)] (R = NO2 1 或 H 2)、[Ni2-(CC)C5H3NR-5}(PPh3)(η-C5H5)] (R = NO2 3 或 H 4) 和 [Au2-(CC)C5H3NR-5}L] (L = PPh3, R = NO2 5 或 H 6; L = PMe3, R = NO2 7) 已被合成并结构表征 3、5 和 6；从结构表征的苯乙炔基复合物到新的吡啶乙炔基复合物，或从 6 到 5 替换 5-H 为 5-NO2 的过程中，乙炔基的醌式乙烯基贡献对乙炔基基态结构的显著增加并不明显。分子二阶非线性光学性质已通过超雷利散射(HRS)测定。HRS 测量在 1064 nm 处与通过用 N-杂环替代苯基 (用硝基吡啶乙炔基取代硝基苯乙炔基配体) 在钌和金系统中增加 β 一致，但对镍复合物没有变化，并且在从 7 到 5 的过程中用 PPh3 替代 PMe3 时非线性增加。通过 Kurtz 粉末测量在 1064 nm 处确定了系列的有效二阶极化率，唯一显著的响应 (约为尿素的八倍) 来自 3；这种复合物是三个结构表征中唯一一个在晶格中非中心对称排列的。获得了 1-4 的电化学数据; 与类似的硝基苯乙炔基复合物比较，用硝基吡啶乙炔基替代硝基苯乙炔基会导致钌复合物的 MII/III 氧化电位显著增加，但对镍复合物没有变化。对 1-4 评估了参数 E°MII/III - E°NO2/NO2，结果 M = Ru 和 Ni 与实验确定的非线性一致，即较小的 ΔE° 和较大的非线性对于钌比镍。
• Stereoselective addition reactions of diphenylphosphine to pyridyl and pyrimidylalkynes: chiral 1,2-diheteroaryl-1,2-bis(diphenylphosphino)ethanes and their Group 6 metal carbonyl complexes
  作者：Jonathan L Bookham、Darren M Smithies

  DOI：10.1016/s0022-328x(98)01078-x

  日期：1999.4

  parent diphosphine. At moderately elevated temperatures, nitrogen coordination of 2-pyridyl and 2-pyrimidyl groups occurred for tetracarbonyl complexes of meso- or erythro-stereochemistry, but not for complexes of rac- or threo-form, to yield corresponding fac-tricarbonyl complexes. At 162°C the complex cis-rac-(CO)4WP,P′-Ph2PCH(R)CH(R)PPh2} (R=R′=2-pyridyl) is converted quantitatively into fac-erythro-(CO)3WP

  碱催化的二苯基膦加到二芳基乙炔RCCR'中（R = R'= 2-吡啶基1 ; R = R'= 3-吡啶基2 ; R = 2-吡啶基，R'= 3-吡啶基3 ; R =苯基，R'= 2-吡啶基4，3-吡啶基5，2-嘧啶基6）通式博士的产率的二膦2 PCH（R）CH（R'）PPH 2与烯烃副产物博士一起2 PC（R ）CHR'和HC（R）C（R'）PPh 2在除1以外的所有情况下都为2。选择的P，P'配位的M（CO）4种复合物（M =钼，钨）的已制备的二膦和它们的1 H-，13给出了13 C -NMR和31 P-NMR数据。明确使用四羰基配合物的13个CO-NMR信号模式确定母体二膦的立体化学。在适度升高的温度，2-吡啶基和2-嘧啶基团的氮协调发生了的四羰络合物内消旋-或赤-立体化学，但不适合的络合物外消旋-或苏-形式，以产生对应的FAC三羰络合物。在162°C下，复杂的顺式-rac-（CO）4
• An Improved Procedure for the Preparation of Aryl- and Hetarylacetylenes
  作者：A. G. Mal’kina、L. Brandsma、S. F. Vasilevsky、B. A. Trofimov

  DOI：10.1055/s-1996-4265

  日期：1996.5

  A number of relatively volatile acetylenes RC≡CH (R = aryl or hetaryl) have been prepared with high yields by heating a mixture of the corresponding alcohols RC≡CC(CH3)2OH and paraffin oil with small amounts of powdered potassium hydroxide in vacuum. The alcohols were obtained by Pd/Cu-catalyzed cross coupling of aryl or hetaryl halides RX (X = Br, in one case I) with the commercially available HC≡CC(CH3)2OH.

  通过在真空条件下加热相应的醇RC≡CC(CH3)2OH与石蜡油及少量粉末状氢氧化钾的混合物，成功制备了一系列相对易挥发的乙炔RC≡CH（R=芳基或杂芳基），产率较高。这些醇是通过钯/铜催化下的芳基或杂芳基卤化物RX（X=溴，有一次碘）与市售的HC≡CC(CH3)2OH进行的交叉偶联反应得到的。

表征谱图