3-bromo-2-octylfuran | 125130-85-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3-bromo-2-octylfuran
• 英文别名: 3-bromo-2-n-octylfuran
• CAS: 125130-85-0
• 化学式: C₁₂H₁₉BrO
• 分子量: 259.186
• InChiKey: FBYVAYUIZUHRFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-bromo-2-octylfuran 在 正丁基锂 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 3-fluoro-2-n-octylfuran
  参考文献：
  名称：

  Synthesis and NMR studies of 2- and 3-fluorosubstitued five-membered heterocycles

  摘要：

  A set of 2-fluoro- and 3-fluoro-substituted thiophenes, pyrroles and furans has been synthesized by a treatment of the corresponding lithio derivatives with N-fluorodibenzenesulfonamide. For all these compounds, (1)J(CC) and (1)J(CH) coupling constants and F-19 NMR chemical shifts have been measured. In all cases, a dramatic increase of the (1)J(C2C3) couplings has been observed in 2-fluoro- and 3-fluoro-substituted compounds in comparison with those measured for the parent compounds. The same is valid for (1)JC(3)C(4) measured in 3-fluoro derivatives.The DFF calculations performed for 2- and 3-fluoro-substituted compounds reproduce very well the experimental coupling values and show that the Fermi contact contribution is the main factor determining their magnitude. Also the trends observed in the F-19 NMR shieldings are well reflected in the calculated DFF data. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2003.07.001
• 作为产物：
  描述：

  (+/-)-4-hydroxydodec-2-ynal diethyl acetal 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以86%的产率得到3-bromo-2-octylfuran
  参考文献：
  名称：

  取代的乙酰酮的酸催化环化反应：3-卤代呋喃，黄酮和苯乙烯基色酮的合成新方法†

  摘要：

  I型乙缩醛（方案1）和III型乙炔酮（方案1），37和38 （方案7）是用于通过酸催化的环化反应合成各种杂环的通用合成前体。通过这种方式，可以以良好至优异的产率合成II和IV型取代的3-卤代呋喃（方案1）以及黄酮和苯乙烯基色酮（方案7）。3-卤代呋喃酮合成中的高度区域选择性（方案4）是HX（X = Cl，Br，I）的区域选择性β加成到乙炔醛和乙炔酮部分的结果。方案5中描述了一种可能的机制。由于3-氟呋喃很容易被金属化和取代，因此这种方法构成了高度取代的呋喃的新合成方法。

  DOI：

  10.1002/hlca.19890720305

文献信息

• Acid-Catalyzed Cyclization Reactions of Substituted Acetylenic Ketones: A new Approach for the Synthesis of 3-Halofurans, Flavones, and Styrylchromones
  作者：Daniel Obrecht

  DOI：10.1002/hlca.19890720305

  日期：1989.5.3

  Acetylenic acetals of type I(Scheme 1) and acetylenic ketones of type III(Scheme 1), 37 and 38(Scheme 7) are versatile synthetic precursors for the synthesis of various heterocycles by acid-catalyzed cyclization reactions. By this way, substituted 3-halofurans of type II and IV(Scheme 1) and flavones and styrylchromones (Scheme 7) can be synthesized in good-to-excellent yields. The high degree of regioselectivity

  I型乙缩醛（方案1）和III型乙炔酮（方案1），37和38 （方案7）是用于通过酸催化的环化反应合成各种杂环的通用合成前体。通过这种方式，可以以良好至优异的产率合成II和IV型取代的3-卤代呋喃（方案1）以及黄酮和苯乙烯基色酮（方案7）。3-卤代呋喃酮合成中的高度区域选择性（方案4）是HX（X = Cl，Br，I）的区域选择性β加成到乙炔醛和乙炔酮部分的结果。方案5中描述了一种可能的机制。由于3-氟呋喃很容易被金属化和取代，因此这种方法构成了高度取代的呋喃的新合成方法。
• Synthesis and NMR studies of 2- and 3-fluorosubstitued five-membered heterocycles
  作者：Elena Dvornikova、Małgorzata Bechcicka、Krystyna Kamieńska-Trela、Adam Krówczyński

  DOI：10.1016/j.jfluchem.2003.07.001

  日期：2003.12

  A set of 2-fluoro- and 3-fluoro-substituted thiophenes, pyrroles and furans has been synthesized by a treatment of the corresponding lithio derivatives with N-fluorodibenzenesulfonamide. For all these compounds, (1)J(CC) and (1)J(CH) coupling constants and F-19 NMR chemical shifts have been measured. In all cases, a dramatic increase of the (1)J(C2C3) couplings has been observed in 2-fluoro- and 3-fluoro-substituted compounds in comparison with those measured for the parent compounds. The same is valid for (1)JC(3)C(4) measured in 3-fluoro derivatives.The DFF calculations performed for 2- and 3-fluoro-substituted compounds reproduce very well the experimental coupling values and show that the Fermi contact contribution is the main factor determining their magnitude. Also the trends observed in the F-19 NMR shieldings are well reflected in the calculated DFF data. (C) 2003 Elsevier B.V. All rights reserved.