1-(2-氟-3-吡啶基)乙醇 | 79574-61-1

• 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: 1-(2-氟-3-吡啶基)乙醇
• 英文名称: 1-(2-Fluoro-3-pyridyl)ethanol
• 英文别名: 1-(2-fluoropyridin-3-yl)ethanol
• CAS: 79574-61-1
• 化学式: C₇H₈FNO
• 分子量: 141.145
• InChiKey: JUYIDKNNTBXRHG-UHFFFAOYSA-N

物化性质

• 沸点：
  115 °C(Press: 13 Torr)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-氟-3-吡啶基)乙醇 在 盐酸 、 manganese(IV) oxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 3-<1-<<<2-(Diethylamino)ethyl>amino>-3-pyridyl>ethenyl>indole
  参考文献：
  名称：

  A new convergent route to 1-substituted ellipticines

  摘要：

  1-(2-Fluoro-4-pyridyl)ethanone was synthesized from 2-fluoropyridine and was ortho-lithiated after activation as the propylene glycol ketal. The resulting 3-lithio derivative was trapped by various electrophiles but reacted in low yield with N-protected 3-indolecarbaldehyde. Model compounds 1-[[[2-(diethylamino)ethyl]amino]-3-pyridyl]ethanol and -ethanone were prepared and selectively condensed with indole. 1-[[[2-(Diethylamino)-ethyl]amino]-3-pyridyl]ethanol and -ethanone bearing a ketal-protected acetyl moiety at the C-4 position have been obtained in high yields starting from the propylene glycol ketal of 1-(2-fluoro-4-pyridyl)ethanone. These reagents could not be condensed with indole either due to side reactions between the C-3 and C-4 functions or to steric hindrance. 1-(2-Substituted-4-bromo-3-pyridyl)ethanols were synthesized via a metalation/halogen-dance strategy starting from 2-fluoropyridine. 1-(2,4-Dihalo-3-pyridyl)-1-chloroethane could be prepared and condensed with 1-indolylmagnesium iodide, which allowed the construction of the expected 3-[1-(3-pyridyl)ethyl]indole skeleton. Functionalization of the pyridine C-4 bromo position was achieved by a vinylstannane cross-coupling reaction using a palladium(0) catalyst. Acidic treatment of the resulting 4-(1-ethoxyethenyl)pyridine led to 1-fluoroellipticine. The whole sequence requires six steps from indole and 2-fluoropyridine and allows an attractive overall yield.

  DOI：

  10.1021/jo00028a032
• 作为产物：
  描述：

  2-氟吡啶 、 乙醛 在 正丁基锂 、 二异丙胺 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 26.0h， 以56%的产率得到1-(2-氟-3-吡啶基)乙醇
  参考文献：
  名称：

  5-Membered heterocyclic compound

  摘要：

  本发明提供了以下通式(I)表示的5元杂环化合物： 本化合物具有优异的抑制胃酸分泌效果，并显示出抗溃疡活性等。

  公开号：

  US20090156642A1

文献信息

• Metallation regioselective en serie pyridinique: Synthese originale d'amino-2 aroyl-3 pyridines
  作者：Timur Güngör、Francis Marsais、Guy Queguiner

  DOI：10.1016/s0022-328x(00)80124-2

  日期：1981.7
• CUENGOER T.; MARSAIS F. QUEGUINER G., J. OF ORGANOMETALL. CHEM., 1981, 215, 139-150
  作者：CUENGOER T.、 MARSAIS F. QUEGUINER G.

  DOI：——

  日期：——
• 5-MEMBERED HETEROCYCLIC COMPOUNDS AS PROTON PUMP INHIBITORS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2190822B1

  公开（公告）日：2014-12-31
• TRIAZOLE CARBAMATE PYRIDYL SULFONAMIDES AS LPA RECEPTOR ANTAGONISTS AND USES THEREOF
  申请人：Gilead Sciences, Inc.

  公开号：US20210171500A1

  公开（公告）日：2021-06-10

  The present disclosure relates generally to compounds that bind to Lysophosphatidic Acid Receptor 1 (LPAR1) and act as antagonists of LPAR1. The disclosure further relates to the use of the compounds for the preparation of a medicament for the treatment of diseases and/or conditions through binding of LPAR1, including fibrosis and liver diseases such as non-alcoholic steatohepatitis (NASH).
• [EN] 5-MEMBERED HETEROCYCLIC COMPOUND<br/>[FR] COMPOSÉ HÉTÉROCYCLIQUE À 5 CHAÎNONS
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2009041705A2

  公开（公告）日：2009-04-02

  The present invention provides compounds represented by the formula (I): The present compounds have a superior acid secretion inhabitory effect, and show a antiulcer activity.