6-乙基吡啶甲酸乙酯 | 41337-78-4

• 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: 6-乙基吡啶甲酸乙酯
• 英文名称: ethyl 6-ethylpyridine-2-carboxylate
• 英文别名: Ethyl 6-ethylpicolinate
• CAS: 41337-78-4
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: VRJCFLQYJFNQKU-UHFFFAOYSA-N

物化性质

• 沸点：
  278.1±28.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  6-乙基吡啶甲酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以870 mg的产率得到2-乙基-6-羟甲基吡啶
  参考文献：
  名称：

  Discovery of Ritonavir, a Potent Inhibitor of HIV Protease with High Oral Bioavailability and Clinical Efficacy

  摘要：

  The structure-activity studies leading to the potent and clinically efficacious HIV protease inhibitor ritonavir are described. Beginning with the moderately potent and orally bioavailable inhibitor A-80987, systematic investigation of peripheral (P3 and P2') heterocyclic groups designed to decrease the rate of hepatic metabolism provided analogues with improved pharmacokinetic properties after oral dosing in rats. Replacement of pyridyl groups with thiazoles provided increased chemical stability toward oxidation while maintaining sufficient aqueous solubility for oral absorption, Optimization of hydrophobic interactions with the HIV protease active site produced ritonavir, with excellent in vitro potency (EC50 = 0.02 mu M) and high and sustained plasma concentrations after oral administration in four species. Details of the discovery and preclinical development of ritonavir are described.

  DOI：

  10.1021/jm970636+
• 作为产物：
  描述：

  5-己烯-3-醇 在 镍 tetrafluoroboric acid 、 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 6-乙基吡啶甲酸乙酯
  参考文献：
  名称：

  使用腈氧化物和高烯丙醇通过环加成路线合成取代吡啶

  摘要：

  腈氧化物与未保护的高烯丙醇的环加成，然后是 Swern 氧化，产生 5-(2-氧代烷基)-2-异恶唑啉。随后在过量四氟硼酸存在下，在乙醇中对所得杂环进行 Raney Ni 还原，得到取代的吡啶衍生物。

  DOI：

  10.1246/bcsj.64.375

文献信息

• NOVEL MORPHOLINE DERIVATIVE OR SALT THEREOF
  申请人：FUJIFILM Corporation

  公开号：US20160168139A1

  公开（公告）日：2016-06-16

  There is provided a morpholine derivative represented by General Formula [1A] or a salt thereof. (In the formula, a ring A represents a ring represented by General Formula [I]; * represents a bonding position; Z 2 represents CH or the like; Z 1 represents CR 6 or the like; R 6 represents a hydrogen atom or the like; X 1 represents CHR 7 or the like; R 7 represents a hydrogen atom or the like; X 2 represents CH 2 or the like; R 1 and R 2 are the same as or different from each other, and each of R 1 and R 2 represents a hydrogen atom or the like; R 3 , R 4 , and R 5 are the same as or different from each other, and each of R 3 , R 4 , and R 5 represents a hydrogen atom, NR a R b , or the like; and each of R a and R b represents a hydrogen atom, a C 1-8 alkyl group which may have a substituent, or the like.)

  提供一种由通用式[1A]表示的吗啉衍生物或其盐。 （在该式中，环A代表由通用式[I]表示的环；*代表连接位置；Z 2 代表CH或类似物；Z 1 代表CR 6 或类似物；R 6 代表氢原子或类似物；X 1 代表CHR 7 或类似物；R 7 代表氢原子或类似物；X 2 代表CH 2 或类似物；R 1 和R 2 相同或不同，且R 1 和R 2 中的每一个代表氢原子或类似物；R 3 ，R 4 和R 5 相同或不同，且R 3 ，R 4 和R 5 中的每一个代表氢原子，NR a R b 或类似物；R a 和R b 中的每一个代表氢原子，可能具有取代基的C 1-8 烷基基团，或类似物。）
• Rh(III)-Catalyzed Regioselective Synthesis of Pyridines from Alkenes and α,β-Unsaturated Oxime Esters
  作者：Jamie M. Neely、Tomislav Rovis

  DOI：10.1021/ja3104389

  日期：2013.1.9

  O-pivaloyl oximes are coupled to alkenes by Rh(III) catalysis to afford substituted pyridines. The reaction with activated alkenes is exceptionally regioselective and high-yielding. Mechanistic studies suggest that heterocycle formation proceeds via reversible C-H activation, alkene insertion, and a C-N bond formation/N-O bond cleavage process.

  α,β-不饱和的 O-新戊酰基肟通过 Rh(III) 催化与烯烃偶联，得到取代的吡啶。与活化烯烃的反应具有异常的区域选择性和高产率。机理研究表明，杂环的形成是通过可逆的 CH 活化、烯烃插入和 CN 键形成/NO 键裂解过程进行的。
• [EN] SUBSTITUTED N-(1H-INDAZOL-4-YL)IMIDAZO[1,2-a]PYRIDINE-3-CARBOXAMIDE COMPOUNDS AS TYPE III RECEPTOR TYROSINE KINASE INHIBITORS<br/>[FR] COMPOSÉS N-(1H-INDAZOL-4-YL)IMIDAZO[1,2-A]PYRIDINE-3-CARBOXAMIDES SUBSTITUÉS EN TANT QU'INHIBITEURS DE TYROSINE KINASE DE RÉCEPTEURS DE TYPE III
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2012082689A1

  公开（公告）日：2012-06-21

  Compounds of Formula I: and pharmaceutically acceptable salts thereof in which R1, R2, R3, R4, R5 and R6 have the meanings given in the specification, are inhibitors of cFMS and are useful in the treatment of fibrosis, bone-related diseases, cancer, autoimmune disorders, inflammatory diseases, cardiovascular diseases, pain and burns in a mammal.

  公式I的化合物及其药学上可接受的盐，在其中R1、R2、R3、R4、R5和R6具有规范中给定的含义，是cFMS的抑制剂，并且在治疗哺乳动物的纤维化、与骨相关的疾病、癌症、自身免疫性疾病、炎症性疾病、心血管疾病、疼痛和烧伤方面是有用的。
• Synthesis of Substituted Pyridines by a Cycloaddition Route Using Nitrile Oxides and Homoallyl Alcohols
  作者：Shuji Kanemasa、Yoshihiko Asai、Junji Tanaka

  DOI：10.1246/bcsj.64.375

  日期：1991.2

  Cycloadditions of nitrile oxides with unprotected homoallyl alcohols, followed by Swern oxidations, lead to 5-(2-oxoalkyl)-2-isoxazolines. Subsequent Raney Ni reduction of the resulting heterocycles in ethanol in the presence of excess tetrafluoroboric acid affords substituted pyridine derivatives.

  腈氧化物与未保护的高烯丙醇的环加成，然后是 Swern 氧化，产生 5-(2-氧代烷基)-2-异恶唑啉。随后在过量四氟硼酸存在下，在乙醇中对所得杂环进行 Raney Ni 还原，得到取代的吡啶衍生物。
• SUBSTITUTED N-(1H-INDAZOL-4-YL)IMIDAZO[1,2-]PYRIDINE-3-CARBOXAMIDE COMPOUNDS AS TYPE III RECEPTOR TYROSINE KINASE INHIBITORS
  申请人：Boys Mark Laurence

  公开号：US20130274244A1

  公开（公告）日：2013-10-17

  Compounds of Formula I: and pharmaceutically acceptable salts thereof in which R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the meanings given in the specification, are inhibitors of cFMS and are useful in the treatment of fibrosis, bone-related diseases, cancer, autoimmune disorders, inflammatory diseases, cardiovascular diseases, pain and burns in a mammal.

  公式I的化合物及其药学上可接受的盐，其中R1、R2、R3、R4、R5和R6的含义如规范中所述，是cFMS的抑制剂，可用于治疗哺乳动物的纤维化、与骨有关的疾病、癌症、自身免疫性疾病、炎症性疾病、心血管疾病、疼痛和烧伤。