3-bromomethyl-4-iodofuran | 1375645-24-1

• 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-bromomethyl-4-iodofuran
• 英文别名: 3-(Bromomethyl)-4-iodofuran；3-(bromomethyl)-4-iodofuran
• CAS: 1375645-24-1
• 化学式: C₅H₄BrIO
• 分子量: 286.895
• InChiKey: YNAPGJBEXBRKET-UHFFFAOYSA-N

物化性质

• 沸点：
  246.4±25.0 °C(Predicted)
• 密度：
  2.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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-bromomethyl-4-iodofuran 在 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 水 、 三正丁基氢锡 、 sodium hydride 、 sodium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 ethyl (E)-3-(4-(2-((5-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)pentyl)oxy)vinyl)furan-3-yl)propanoate
  参考文献：
  名称：

  Toward the total synthesis of Luminamicin: construction of 14-membered lactone framework possessing versatile enol ether moiety

  摘要：

  Luminamicin (1) was found to exhibit selective antibacterial activity against anaerobic bacteria by our group in 1985. The concise structure of 14-membered lactone of 1 was synthesized. Construction of a versatile enol ether moiety was achieved by Stille cross coupling via hydrostanylation of the ethynyl ether, and a maleic anhydride moiety was derived from the furan constitution by the oxidation after the macrolactonization at a late-stage. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.098
• 作为产物：
  描述：

  (4-Iodofuran-3-yl)methanol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以100%的产率得到3-bromomethyl-4-iodofuran
  参考文献：
  名称：

  Toward the total synthesis of Luminamicin: construction of 14-membered lactone framework possessing versatile enol ether moiety

  摘要：

  Luminamicin (1) was found to exhibit selective antibacterial activity against anaerobic bacteria by our group in 1985. The concise structure of 14-membered lactone of 1 was synthesized. Construction of a versatile enol ether moiety was achieved by Stille cross coupling via hydrostanylation of the ethynyl ether, and a maleic anhydride moiety was derived from the furan constitution by the oxidation after the macrolactonization at a late-stage. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.098

文献信息

• Toward the total synthesis of Luminamicin: construction of 14-membered lactone framework possessing versatile enol ether moiety
  作者：Aoi Kimishima、Tomoyasu Hirose、Akihiro Sugawara、Takanori Matsumaru、Kaoru Nakamura、Ken Katsuyama、Masaki Toda、Hirokazu Takada、Rokuro Masuma、Satoshi Ōmura、Toshiaki Sunazuka

  DOI：10.1016/j.tetlet.2012.03.098

  日期：2012.6

  Luminamicin (1) was found to exhibit selective antibacterial activity against anaerobic bacteria by our group in 1985. The concise structure of 14-membered lactone of 1 was synthesized. Construction of a versatile enol ether moiety was achieved by Stille cross coupling via hydrostanylation of the ethynyl ether, and a maleic anhydride moiety was derived from the furan constitution by the oxidation after the macrolactonization at a late-stage. (C) 2012 Elsevier Ltd. All rights reserved.