2,4-dimethyl-3-(pyridin-2-yl)pentan-3-ol | 151200-96-3

• 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
• 英文名称: 2,4-dimethyl-3-(pyridin-2-yl)pentan-3-ol
• 英文别名: 2,4-dimethyl-3-(2-pyridyl)-pentan-3-ol；(2'-pyridyl)-2,4-dimethylpentan-3-ol；2,4-Dimethyl-3-pyridin-2-ylpentan-3-ol
• CAS: 151200-96-3
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: OFKLYXUSGNMQDM-UHFFFAOYSA-N

物化性质

• 沸点：
  85-88 °C(Press: 0.2 Torr)
• 密度：
  0.980±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  2,4-dimethyl-3-(pyridin-2-yl)pentan-3-ol 、 bis((trimethylsilyl)methyl)zinc 以 乙醚 为溶剂， 生成 bis((trimethylsilyl)methyl)zinc(2,4-dimethyl-3-(2-pyridyl)3-pentoxide)
  参考文献：
  名称：

  Organozinc complexes with monoanionic chelating phenolates or 2-pyridylmethanolates. Molecular structure of [Zn(CH2SiMe3){OCH2(2-Py)}]4

  摘要：

  The influence of the chelate ring size and of the presence of sterically demanding groups in the chelating ligand on the degree of association of organozinc ortho-substituted phenolates and alpha-substituted 2-pyridylmethanolates has been studied. Organozinc derivatives were made of phenols with one or two potentially ortho-chelating (dimethylamino)methyl groups and of the alpha-substituted 2-pyridylmethanols, 2-(2-pyridyl)propan-2-ol, 2,4-dimethyl-3-(2-pyridyl)pentan-3-ol, diphenyl-2-pyridylmethanol, 1-phenyl-1-(2-pyridyl)ethanol, and 2,2-dimethyl-1-(2-pyridyl)-propanol. The CH2NMe2-substituted phenolate compound 1a, containing a six-membered chelate ring via Zn-N coordination is dimeric, whereas compounds 2b and 2b', having two CH2NMe2 substituents in the phenolate ligand, exist in benzene as a monomer-dimer equilibrium. The alkylzinc 2-pyridylmethanolate complexes 3c and 3c', in which intramolecular Zn-N coordination leads to a five-membered chelate ring, are trimeric in solution. Surprisingly, 3c is a tetramer in the solid state. Introduction of substituents in the five-membered chelate ring of these 2-pyridylmethanolates affects the stability of the aggregates in solution. Complexes 3d and 3g, with small substituents on the a-carbon atoms of the pyridylcarbinolate fragment, exist in solution as equilibria of dimers and trimers, whereas compounds 3e, 3f, and 3h, with more sterically demanding a-substituents, are concentration independent dimers in solution. The molecular structure of tetrameric 3c in the solid state contains a puckered eight-membered Zn4O4 ring in which the zinc atoms are coordinatively saturated by four intramolecularly coordinating pyridyl fragments. Crystals of [Zn(CH2SiMe3){OCH2(2-PY)}]4, 3c, are monoclinic, space group P2(1)/c with unit-cell dimensions a = 12.625(1) angstrom, b = 17.815(1) angstrom, c = 12.299(1) angstrom, beta = 111.23(1)-degrees, and final R = 0.028.

  DOI：

  10.1021/om00033a039
• 作为产物：
  描述：

  吡啶 、 2,4-二甲基-3-戊酮 在 氢化铝 、 汞 、 mercury dichloride 作用下， 生成 2,4-dimethyl-3-(pyridin-2-yl)pentan-3-ol
  参考文献：
  名称：

  组胺拮抗剂；基本取代的吡啶衍生物。

  摘要：

  DOI：

  10.1021/ja01192a010

文献信息

• Improved Metathesis Lifetime: Chelating Pyridinyl-Alcoholato Ligands in the Second Generation Grubbs Precatalyst
  作者：Jean du Toit、Margaritha Jordaan、Carlijn Huijsmans、Johannes Jordaan、Cornelia van Sittert、Hermanus Vosloo

  DOI：10.3390/molecules19055522

  日期：——

  Hemilabile ligands can release a free coordination site “on demand” of an incoming nucleophilic substrate while occupying it otherwise. This is believed to increase the thermal stability and activity of catalytic systems and therefore prevent decomposition via free coordination sites. In this investigation chelating pyridinyl-alcoholato ligands were identified as possible hemilabile ligands for incorporation into the second generation Grubbs precatalyst. The O,N-alcoholato ligands with different steric bulk could be successfully incorporated into the precatalysts. The incorporation of the sterically hindered, hemilabile O,N-ligands improved the thermal stability, activity, selectivity and lifetime of these complexes towards the metathesis of 1-octene. A decrease in the activity of the second generation Grubbs precatalyst was additionally observed after incorporating a hemilabile O,N-ligand with two phenyl groups into the system, while increasing their lifetime.

  半亲和配体可以 "按需 "释放进入的亲核底物的自由配位位点，而不占用该位点。这被认为可以提高催化系统的热稳定性和活性，从而防止通过游离配位位点发生分解。在这项研究中，螯合吡啶醇配体被确定为可能加入第二代格拉布斯前催化剂的可亲血配体。具有不同立体体积的 O,N-醇配体可以成功地加入到前催化剂中。掺入立体受阻的半亲和 O,N-配体提高了这些配合物在 1-辛烯偏析过程中的热稳定性、活性、选择性和寿命。此外，在体系中加入带有两个苯基的半亲和 O,N-配体后，第二代格拉布斯前催化剂的活性降低了，但寿命却延长了。
• New dioxomolybdenum(VI) catalysts for the selective oxidation of terminal n-alkenes with molecular oxygen
  作者：Wolfgang A. Herrmann、Gerhard M. Lobmaier、Thomas Priermeier、Mike R. Mattner、Bernd Scharbert

  DOI：10.1016/s1381-1169(96)00381-0

  日期：1997.3

  presence of 2. An additional advantage is that the catalyst can be recovered. The synthesis and the characterization of the new dixomolybdenum(VI) complexes and the ligands is described in addition to their catalytic properties. The structure of the new complex bis[N,O-(2′-pyridyl)pentan-3-olato}]dioxomolybdenum(VI) (2) was determined by X-ray diffraction: monoclinic space group P , a = 1444.5(2)

  MoO 2 L 2 [L =（2'-吡啶基）醇]型新的二氧钼钼（VI）络合物能够显着改变金属催化的自氧化过程的产物分布。使用催化剂双[ N，O -（2'-吡啶基）戊基-3-olato}]二氧钼（VI）（2），在1-辛烯的自氧化过程中形成环氧化物作为主要产物。在2的存在下用分子氧（1 bar和100°C）处理1-辛烯时，产物的选择性从24％（环氧，自氧化）增加到58％。另一个优点是可以回收催化剂。除了其催化性能之外，还描述了新的二钼（VI）配合物和配体的合成和表征。通过X射线衍射确定新的复合物bis [ N，O -（2'-吡啶基）戊丹-3-olato}]二氧钼（VI）（2）的结构：单斜空间群P ，a = 1444.5（ 2）时，b = 1052.4（1）时，ç = 1511.5（2）时，β= 115.86（1）°， 。环氧化数据表明催化剂的配体球对产物分布的重要影响。现在，我们可以对金属催化的自氧化反应中的配合物进行微调。
• Friedel–Crafts Reactions with <i>N</i>-Heterocyclic Alcohols
  作者：Jacob C. Hood、Maksim V. Anokhin、Douglas A. Klumpp

  DOI：10.1021/acs.joc.3c00403

  日期：2023.8.4

  N-Heterocyclic alcohols are shown to be excellent substrates for superacid-promoted Friedel–Crafts reactions. The N-heterocyclic alcohols ionize to produce reactive, dicationic intermediates which provide good to excellent yields of arylation products.

  N-杂环醇被证明是超强酸促进的弗里德尔-克来福特反应的优良底物。N-杂环醇电离产生反应性双阳离子中间体，其提供良好至极好的芳基化产物产率。
• US5969166A
  申请人：——

  公开号：US5969166A

  公开（公告）日：1999-10-19
• Histamine Antagonists. Basically Substituted Pyridine Derivatives
  作者：Charles H. Tilford、Robert S. Shelton、M. G. van Campen

  DOI：10.1021/ja01192a010

  日期：1948.12