Tert-butyl 2-(bromomethyl)furan-3-carboxylate | 896735-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: Tert-butyl 2-(bromomethyl)furan-3-carboxylate
• CAS: 896735-97-0
• 化学式: C₁₀H₁₃BrO₃
• 分子量: 261.115
• InChiKey: BFLUYNIKABMPBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-(bromomethyl)furan-3-carboxylate 在 selenium(IV) oxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 苯 为溶剂， 反应 2.33h， 生成 2-((1R,2S,4R)-2-Hydroxy-4-methoxycarbonyl-3-methylene-cyclobutyl)-furan-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A biogenetically patterned synthetic approach to the unusual furan methylenecyclobutanol moiety in providencin

  摘要：

  Irradiation of a solution of alpha,beta-unsaturated aldehyde 10 in benzene leads to the methylenecyclobutanol 11 by way of a novel intrarnolecular C-H insertion reaction. The conversion of 10 into 11 has relevance to the possible origin of the cyclobutane ring-based furanocembrane providencin 1 found in gorgonian octocorals. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.158
• 作为产物：
  描述：

  2-甲基-3-糠酸 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 硫酸 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 Tert-butyl 2-(bromomethyl)furan-3-carboxylate
  参考文献：
  名称：

  A biogenetically patterned synthetic approach to the unusual furan methylenecyclobutanol moiety in providencin

  摘要：

  Irradiation of a solution of alpha,beta-unsaturated aldehyde 10 in benzene leads to the methylenecyclobutanol 11 by way of a novel intrarnolecular C-H insertion reaction. The conversion of 10 into 11 has relevance to the possible origin of the cyclobutane ring-based furanocembrane providencin 1 found in gorgonian octocorals. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.158

文献信息

• A biogenetically patterned synthetic approach to the unusual furan methylenecyclobutanol moiety in providencin
  作者：Christopher D. Bray、Gerald Pattenden

  DOI：10.1016/j.tetlet.2006.03.158

  日期：2006.6

  Irradiation of a solution of alpha,beta-unsaturated aldehyde 10 in benzene leads to the methylenecyclobutanol 11 by way of a novel intrarnolecular C-H insertion reaction. The conversion of 10 into 11 has relevance to the possible origin of the cyclobutane ring-based furanocembrane providencin 1 found in gorgonian octocorals. (c) 2006 Elsevier Ltd. All rights reserved.