2-methyl-1-(pyridine-2-yl)propan-1-ol | 102439-95-2

• 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-1-(pyridine-2-yl)propan-1-ol
• 英文别名: 2-methyl-1-(pyridin-2-yl)-1-propanol；2-methyl-1-(pyridin-2-yl)propan-1-ol；α-isopropyl(2-pyridyl)methanol；2-methyl-1-[2]pyridyl-propan-1-ol；2-methyl-1-pyridin-2-ylpropan-1-ol
• CAS: 102439-95-2
• 化学式: C₉H₁₃NO
• mdl: MFCD12153509
• 分子量: 151.208
• InChiKey: CWQKDQOZSPOCRK-UHFFFAOYSA-N

物化性质

• 沸点：
  238.8±15.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 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-1-(pyridine-2-yl)propan-1-ol 在 四溴化碳 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.75h， 生成 (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-((S)-2-methyl-1-(pyridin-2-yl)propyl)piperidin-2-one
  参考文献：
  名称：

  Discovery of Potent and Simplified Piperidinone-Based Inhibitors of the MDM2–p53 Interaction

  摘要：

  Continued optimization of the N-substituent in the piperidinone series provided potent piperidinone-pyridine inhibitors 6, 7, 14, and 15 with improved pharmacokinetic properties in rats. Reducing structure complexity of the N-alkyl substituent led to the discovery of 23, a potent and simplified inhibitor of MDM2. Compound 23 exhibits excellent pharmacokinetic properties and substantial in vivo antitumor activity in the SJSA-1 osteosarcoma xenograft mouse model.

  DOI：

  10.1021/ml500142b
• 作为产物：
  描述：

  2-氰基吡啶 在 sodium tetrahydroborate 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-methyl-1-(pyridine-2-yl)propan-1-ol
  参考文献：
  名称：

  Rhodium Catalyzed Asymmetric Hydrogenation of 2-Pyridine Ketones

  摘要：

  Catalyzed by [Rh(COD)Binapine]BF4, the asymmetric hydrogenation of 2-pyridine ketones has been achieved with excellent enantioselectivities (enantiomeric excesses up to 99%) under mild conditions. This method is suitable for various kinds of 2-pyridine ketones and their derivatives. A number of enantiomerically pure chiral 2-pyridine-aryl/alkyl alcohols were prepared through hydrogenation, which can be used directly in organic synthesis.

  DOI：

  10.1021/acs.orglett.5b01878

文献信息

• Synthesis, Structure–Activity Relationships, and Preclinical Evaluation of Heteroaromatic Amides and 1,3,4-Oxadiazole Derivatives as 5-HT₄ Receptor Partial Agonists
  作者：Ramakrishna Nirogi、Abdul Rasheed Mohammed、Anil K. Shinde、Shankar Reddy Gagginapally、Durga Malleshwari Kancharla、Vanaja Reddy Middekadi、Narsimha Bogaraju、Srinivasa Rao Ravella、Pooja Singh、Sumit Raosaheb Birangal、Ramkumar Subramanian、Raghava Choudary Palacharla、Vijay Benade、Nageswararao Muddana、Pradeep Jayarajan

  DOI：10.1021/acs.jmedchem.8b00457

  日期：2018.6.14

  scaffolds having 5-HT4R pharmacophores were designed and evaluated. Most of the synthesized compounds showed potent in vitro affinities and in vivo efficacies. Upon analysis of focused structure–activity relationships, compound 4o was identified as a potent 5-HT4R partial agonist with favorable ADME properties and good in vivo efficacy. GR-125487, a selective 5-HT4R antagonist, attenuated the activity

  阿尔茨海默氏病（AD）是一种神经退行性疾病，在60岁以上的人群中患病率和发病率较高。改进的AD疗法的需求未得到满足，因为当前疗法对症且疗效中等。5-HT 4受体（5-HT 4 R）的部分激动剂可通过激活α-分泌酶将淀粉样蛋白前体蛋白（APP）的处理过程从淀粉样蛋白生成途径转变为非淀粉样蛋白生成途径，从而提供对症和疾病缓解治疗。酶。此外，它们还通过增加大脑中神经递质乙酰胆碱的水平来提供对症治疗。由于这种引人入胜的双重作用机理，几种具有5-HT 4的化学支架设计并评估了R药效团。大多数合成的化合物显示出有效的体外亲和力和体内功效。通过分析集中的结构与活性之间的关系，化合物4o被确定为有效的5-HT 4 R部分激动剂，具有良好的ADME特性和良好的体内功效。GR-125487，一种选择性的5-HT 4 R拮抗剂，减弱了新对象识别测试认知模型中化合物4o的活性。
• sp³C–H bond alkylation of ketones with alkenes via ruthenium(<scp>ii</scp>) catalysed dehydrogenation of alcohols
  作者：Bin Li、Christophe Darcel、Pierre H. Dixneuf

  DOI：10.1039/c4cc00931b

  日期：——

  The sp(3)C-H bond functionalisation of 2-pyridyl ethanols upon reaction with alkenes, in the presence of a [RuCl2(arene)]2 catalyst and Cu(OAc)2.H2O, is performed under mild conditions without additional base. This reaction proceeds via a tandem alcohol dehydrogenation/alkylation with alkenes of the resulting ketone at its alpha sp(3)C-H bond.

  在[RuCl2（arene）] 2催化剂和Cu（OAc）2.H2O存在下，在与烯烃反应后，2-吡啶基乙醇的sp（3）CH键官能化反应在温和的条件下进行，无需额外的碱。该反应通过与所得酮的烯烃在其αsp（3）CH键处的串联醇脱氢/烷基化而进行。
• N-alkylation of lactams with secondary heterobenzylic bromides
  作者：Ming Yu、Karis Stevenson、Gene Zhou

  DOI：10.1016/j.tetlet.2014.08.060

  日期：2014.10

  We herein report a general N-alkylation reaction of lactams with secondary heterobenzylic bromides. This methodology features mild reaction condition, moderate to high product isolation yield, and broad substrate scope. Good chemical and structural tolerance has also been demonstrated by both the secondary heterobenzylic bromides and lactam substrates.

  我们在此报道内酰胺与仲杂苄基溴化物的一般N-烷基化反应。该方法的特点是反应条件温和，产物分离产率中等到高以及底物范围广。二级杂苄基溴化物和内酰胺底物也证明了良好的化学和结构耐受性。
• Double Duty for Cyanogen Bromide in a Cascade Synthesis of Cyanoepoxides
  作者：Zhou Li、Vladimir Gevorgyan

  DOI：10.1002/anie.201006966

  日期：2011.3.14

  An unprecedented reaction mode of cyanogen bromide has been discovered. Under basic conditions, cyanogen bromide acts as an equivalent of both Br+ and CN− to convert enolizable ketones into the corresponding cyanoepoxides in good yields. This unique reaction mode provides new, one‐pot access to densely substituted cyanoepoxides from easily available ketones (see scheme).

  已经发现了前所未有的溴化氰反应模式。在碱性条件下，溴化氰同时充当Br中的等效+和CN -至烯醇化的酮转化成良好产率的相应cyanoepoxides。这种独特的反应模式为从容易获得的酮类中稠密取代的氰基环氧化物提供了新的一锅通（见方案）。
• Tunable System for Electrochemical Reduction of Ketones and Phthalimides
  作者：Yaxin Wang、Jianyou Zhao、Tianjiao Qiao、Jian Zhang、Gong Chen

  DOI：10.1002/cjoc.202100508

  日期：2021.12

  Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN3 as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously

  在此，我们报告了一种高效、可调的系统，用于在室温下电化学还原酮和邻苯二甲酰亚胺，无需化学计量的外部还原剂。通过使用 NaN 3作为电解质和石墨毡作为阴极和阳极，我们能够通过明智地选择溶剂和酸性添加剂，将基材的羰基选择性地还原为醇、频哪醇或亚甲基。反应条件与多种官能团兼容，邻苯二甲酰亚胺可以进行一锅还原环化反应，得到带有吲哚里西啶支架的产物。机理研究表明，反应涉及电子、质子和氢原子的转移。重要的是，N 3 /HN 3 循环作为氢原子穿梭运行，这对于将羰基还原为亚甲基至关重要。