3-(3-Bromopropyl)furan | 98126-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(3-Bromopropyl)furan
• 英文别名: 3-(3-furyl)propyl bromide
• CAS: 98126-48-8
• 化学式: C₇H₉BrO
• 分子量: 189.052
• InChiKey: KMIWOOJKAHQDHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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-(3-Bromopropyl)furan 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 15.5h， 生成 3-[(11E,15E)-4,8,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaenyl]furan
  参考文献：
  名称：

  Concise synthesis and structure–activity relationship of furospinosulin-1, a hypoxia-selective growth inhibitor from marine sponge

  摘要：

  Structure activity relationship of furospinosulin-1 (1), a hypoxia-selective growth inhibitor isolated from marine sponge, was investigated. Concise synthetic method of 1 was developed, and some structurally modified analogues were prepared. Biological evaluation of them revealed that the whole chemical structure was important for the hypoxia-selective growth inhibitory activity of 1. Among prepared, the desmethyl analogue 30 showed excellent hypoxia-selective inhibitory activity similar to that of 1 and also exhibited in vivo anti-tumor activity with oral administration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.009
• 作为产物：
  描述：

  3-<3-<(4-Methylbenzenesulfonyl)oxy>propyl>furan 在 lithium bromide 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以1.9938 g的产率得到3-(3-Bromopropyl)furan
  参考文献：
  名称：

  阳极环化，七元环以及自由基阳离子与自由基途径的选择

  摘要：

  尽管氧化环化反应中的许多步骤可能很重要，但环化步骤本身才是中心作用。如果此步骤无法顺利进行，则其余序列的优化是徒劳的。我们在这里报告，环化的关键是引导反应沿着正确的途径进行。一些反应需要使用自由基途径，而某些则需要使用自由基阳离子途径。提供了每个示例的示例，以及使用公用中间体访问两个路径的策略。

  DOI：

  10.1002/cjoc.201900132

文献信息

• Total Synthesis of (−)-Ircinianin and (+)-Wistarin
  作者：Jun'ichi Uenishi、Reiko Kawahama、Osamu Yonemitsu

  DOI：10.1021/jo961993f

  日期：1997.3.1

  (-)-Ircinianin (1), a cyclic furanosesterterpenetetronic acid isolated from a marine sponge (genus Ircinia), is synthesized in 17 steps from (S)-2-methylpropane-1,3-diol mono THP ether 10 and 3-furfural. The key step involves a NiCl2-CrCl2-mediated coupling reaction of iodotriene 9 with chiral aldehyde 8 in DMSO and subsequent intramolecular Diels-Alder reaction in one pot. Both reactions proceed very smoothly at room temperature and eventually give the cyclic product 30A possessing the desired cyclic skeleton of 1 in 60% yield. The structure of 30A is determined by X-ray crystallographic analysis. The stereochemistry of Diels-Alder reactions of 7A and another acyclic precursor 7B are discussed. The first total synthesis of(+)-wistarin (2) is accomplished in 55% yield by iodoether ring formation of 1 and hydrogenolysis of the iodide 33A. Based on the coupling constant in the proton NMR spectrum of 33A, the reported structure 2A is revised to 2B.

  (-)-Ircinianin (1)，一种从海海绵（Ircinia属）中分离出的环状糠酸酯倍半萜四烯酸，通过(S)-2-甲基丙烷-1,3-二醇单THP醚(10)和3-糠醛在17步反应中合成。关键步骤涉及在DMSO中，NiCl₂-CrCl₂介导的碘代三烯(9)与手性醛(8)之间的偶联反应，随后在同一锅中进行分子内Diels-Alder反应。这两个反应在室温下进行得非常顺利，最终以60%的收率得到环状产物30A，其具有目标化合物1所需的环状骨架。通过X射线晶体学分析确定了30A的结构。讨论了Diels-Alder反应中7A和另一个非环前体7B的立体化学。通过1和碘醚环的形成以及碘化物33A的氢解，首次完成了(+)-wistarin (2)的全合成，产率为55%。根据33A的¹H NMR光谱中的偶合常数，对报道的结构2A进行了修订，最终结构为2B。
• Annulated heterocycles through a radical-cation cyclization: synthetic and mechanistic studies
  作者：Jeffrey B. Sperry、Dennis L. Wright

  DOI：10.1016/j.tet.2006.03.058

  日期：2006.7

  and thiophenes, especially reactions leading to dearomatization of the nucleus, make them highly versatile synthons for complex molecule construction. As part of a program to exploit this intrinsic reactivity, we have developed a convenient method to prepare annulated versions of these heterocycles. The strategy is based on a two-step annulation involving the initial conjugate addition of a heteroaryl

  呋喃和噻吩可能进行广泛的化学转化，特别是导致原子核脱芳构的反应，使其成为用于复杂分子构建的高度通用的合成子。作为开发这种内在反应性的计划的一部分，我们已经开发了一种方便的方法来制备这些杂环的环状形式。该策略基于两步退火，其中包括将杂芳基有机金属初始共轭添加到烯酮中，同时捕获烯醇盐作为甲硅烷基烯醇醚。该分子的阳极氧化导致自由基阳离子的最初形成，该自由基阳离子被杂芳基封端的环化捕获，从而得到环状产物。
• Furans in Synthesis. The Preparation of Spiro-Cyclic Systems.
  作者：Steven P. Tanis、Paul M. Herrinton、Lisa A. Dixon

  DOI：10.1016/s0040-4039(00)98204-2

  日期：1985.1

  Furan-terminated cationic cyclizations allylic alcohols, enones, and N-acyl iminium ions as initiators have been explored as routes to highly functionalized spiro[4,5]decanes, spiro[5,5]undecanes, spiro[4,6]undecanes, and spiro[5,6]dodecanes.

  已研究了呋喃封端的阳离子环化烯丙醇，烯酮和N-酰基亚胺离子作为引发剂，作为通往高度官能化的螺[4,5]癸烷，螺[5,5]十一烷，螺[4,6]十一烷的途径，和螺[5,6]十二烷。
• Synthesis of Polycyclic Heterocycles via a One-Pot Ortho Alkylation/Direct Heteroarylation Sequence
  作者：Andrew Martins、Dino Alberico、Mark Lautens

  DOI：10.1021/ol061859+

  日期：2006.10.1

  Polycyclic thiophenes and furans were synthesized using a one-pot ortho alkylation/direct heteroarylation reaction sequence. Under the optimized reaction conditions, aryl iodides were coupled with 3-(bromoalkyl) thiophenes or -furans, affording six-and seven-membered annulated ring products via formation of two C-C bonds from two aryl C-H bonds.
• Furans in synthesis. 5. Furan-terminated cationic cyclizations in the preparation of fused, spirocyclic and bridged ring systems. An application to the synthesis of nakafuran 9
  作者：Steven P. Tanis、Paul M. Herrinton

  DOI：10.1021/jo00221a008

  日期：1985.10