5-methyl-2-picolinic acid | 1609562-68-6

• 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: 5-methyl-2-picolinic acid
• 英文别名: N,N-diethyl-5-methylpicolinamide；N,N-diethyl-5-methylpyridine-2-carboxamide
• CAS: 1609562-68-6
• 化学式: C₁₁H₁₆N₂O
• 分子量: 192.261
• InChiKey: KGXWZEBOLWSDKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-2-picolinic acid 、 丙烯酸乙酯 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以95%的产率得到ethyl (E)-3-[2-(diethylcarbamoyl)-5-methylpyridin-3-yl]acrylate
  参考文献：
  名称：

  铑（III）催化的Picolinamides的氧化烯烃氧化反应：3-Alkenylpicolinamides的便捷合成

  摘要：

  已开发了铑（III）催化的吡啶甲酰胺衍生物的选择性烯烃化反应。该反应显示出高区域选择性，低催化剂负载量（0.5 mol％），高收率和良好的官能团耐受性，为合成3-链烯基吡啶甲酸酰胺提供了便利的策略。

  DOI：

  10.1002/adsc.201300895
• 作为产物：
  描述：

  5-甲基-2-甲酸吡啶 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 5-methyl-2-picolinic acid
  参考文献：
  名称：

  Efficient Synthesis of Isoquinolines via Rh(III)-Catalyzed Oxidative Annu­lation of Picolinamides with Alkynes

  摘要：

  An efficient synthesis of isoquinolines via Rh(III)-catalyzed oxidative annulation of picolinamides with alkynes using Cu(OAc)(2) as an oxidant has been developed. The scope of the reaction was studied with a selection of various picolinamides and alkynes, and the desired isoquinolines were obtained in good to excellent yields.

  DOI：

  10.1055/s-0033-1340870

文献信息

• [EN] IMIDAZO [1,5-A] PYRAZINE DERIVATIVES AS PI3Kdelta INHIBITORS<br/>[FR] DÉRIVÉS D'IMIDAZO [1,5-A] PYRAZINE EN TANT QU'INHIBITEURS DE PI3KDELTA
  申请人：BEIGENE LTD

  公开号：WO2018103688A1

  公开（公告）日：2018-06-14

  Disclosed is a compound of Formula (I), or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, and pharmaceutical compositions comprising thereof. Also disclosed is a method of treating PI3Kδ related disorders or diseases by using the compound disclosed herein.

  揭示的是化合物的化学式（I），或其立体异构体，或其药学上可接受的盐，以及包含其的药物组合物。还公开了利用此处披露的化合物治疗PI3Kδ相关疾病或疾病的方法。
• Spirocyclic Heterocyclic Derivatives And Methods Of Their Use
  申请人：Dolle E. Roland

  公开号：US20080102031A1

  公开（公告）日：2008-05-01

  Spirocyclic heterocyclic derivatives, pharmaceutical compositions containing these compounds, and methods for their pharmaceutical use are disclosed. In certain embodiments, the spirocyclic heterocyclic derivatives are ligands of the δ opioid receptor and may be useful, inter alia, for treating and/or preventing pain, anxiety, gastrointestinal disorders, and other δ opioid receptor-mediated conditions.

  本发明公开了螺环异杂环衍生物、含有这些化合物的制药组合物以及它们的制药用途方法。在某些实施例中，螺环异杂环衍生物是δ阿片受体的配体，可能有助于治疗和/或预防疼痛、焦虑、胃肠疾病和其他δ阿片受体介导的疾病等。
• SPIROCYCLIC HETEROCYCLIC DERIVATIVES AND METHODS OF THEIR USE
  申请人：Dolle Roland E.

  公开号：US20100029614A1

  公开（公告）日：2010-02-04

  Spirocyclic heterocyclic derivatives, pharmaceutical compositions containing these compounds, and methods for their pharmaceutical use are disclosed. In certain embodiments, the spirocyclic heterocyclic derivatives are ligands of the δ opioid receptor and may be useful, inter alia, for treating and/or preventing pain, anxiety, gastrointestinal disorders, and other δ opioid receptor-mediated conditions.

  本发明公开了螺环杂环衍生物、含有这些化合物的制药组合物以及它们的制药用途的方法。在某些实施例中，螺环杂环衍生物是δ阿片受体的配体，并且可能有用于治疗和/或预防疼痛、焦虑、胃肠障碍和其他δ阿片受体介导的疾病等方面。
• Photo‐Excited Nickel‐Catalyzed Silyl‐Radical‐Mediated Direct Activation of Carbamoyl Chlorides To Access (Hetero)aryl Carbamides**
  作者：Sudip Maiti、Sayan Roy、Pintu Ghosh、Aashi Kasera、Debabrata Maiti

  DOI：10.1002/anie.202207472

  日期：2022.11.2

  AbstractAmide bonds connect the amino acids in proteins and exist as a prevalent structural motif in biomolecules. Herein, we have exploited the concept of cross‐electrophile coupling by merging the photo‐redox and transition‐metal catalysis to construct carbamides from superabundant (hetero)aryl halides along with commercially feasible carbamoyl chlorides. The success of this method relies on the prior formation of NiII‐aryl halide intermediates, which involves in a photoexcited Ni‐halide homolysis event by energy transfer from aryl bromide and single‐electron transfer from aryl chloride to assist generation of the vital carbamoyl radical. The breadth of application of this technique is demonstrated both in inter‐ as well as intramolecular routes for the synthesis of a plethora of (hetero)aryl carbamides with diverse functionalities, and biologically important benzolactams.
• US7338962B2
  申请人：——

  公开号：US7338962B2

  公开（公告）日：2008-03-04