2-(furan-2-yl)propan-1-ol | 132819-58-0

• 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: 2-(furan-2-yl)propan-1-ol
• 英文别名: 2-(2-furyl)propan-1-ol；2-(2'-furyl)propanol
• CAS: 132819-58-0
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: GSBVYNOYBBIMJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(furan-2-yl)propan-1-ol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到
  参考文献：
  名称：

  Synthesis of the Tricyclic Ring Structure of Daphnanes via Intramolecular [4 + 3] Cycloaddition/SmI₂-Pinacol Coupling

  摘要：

  A synthetic approach toward the tricyclic 5,7,6-membered ring structure Of daphnane-family natural products is described. An intramolecular [4 + 3] cycloaddition reaction of furan with an oxypentadienyl cation constructed the oxa-bridged bicyclic structure in a stereoselective fashion. Structural analysis revealed that the desired exo isomer was predominantly acquired through epimerization. Finally, formation of the five-membered ring was achieved through SmI2-mediated pinacol coupling.

  DOI：

  10.1021/acs.orglett.5b01054
• 作为产物：
  描述：

  2-丙-1-烯-2-基呋喃 在 硼烷 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.75h， 以20.1 g的产率得到2-(furan-2-yl)propan-1-ol
  参考文献：
  名称：

  Enzymatic kinetic resolution of 1-(3′-furyl)-3-buten-1-ol and 2-(2′-furyl)-propan-1-ol

  摘要：

  The enzymatic kinetic resolution of the racemic alcohols 1-(3'-furyl)-3-buten-1-ol(+/-)-1 and 2-(2'-furyl)propan-1-ol (+/-)-2 was investigated by screening a range of lipases and esterases for enantioselective transacylation, as well as for enantioselective hydrolysis. For both alcohols, lipase-catalyzed hydrolysis of the derived racemic acetate gave the best results for accessing the desired (S)-enantiomers. In the case of the secondary alcohol (+/-)-1 ASL turned out to be the optimum enzyme, whereas PPL was found to be superior in the case of the primary alcohol (+/-)-2. Additionally, an alternative access to (S)-2 via Oppolzer's camphor sultam methodology is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00023-x

文献信息

• Donor–Acceptor Complex Enables Alkoxyl Radical Generation for Metal‐Free C(sp ³ )–C(sp ³ ) Cleavage and Allylation/Alkenylation
  作者：Jing Zhang、Yang Li、Ruoyu Xu、Yiyun Chen

  DOI：10.1002/anie.201707171

  日期：2017.10.2

  The alkoxyl radical is an essential and prevalent reactive intermediate for chemical and biological studies. Here we report the first donor–acceptor complex‐enabled alkoxyl radical generation under metal‐free reaction conditions induced by visible light. Hantzsch ester forms the key donor–acceptor complex with N‐alkoxyl derivatives, which is elucidated by a series of spectrometry and mechanistic experiments

  烷氧基是化学和生物学研究必不可少的，普遍的反应性中间体。在这里，我们报告了在可见光诱导的无金属反应条件下，第一批供体-受体配合物使能的烷氧基自由基的产生。Hantzsch酯与N烷氧基衍生物形成了关键的供体-受体配合物，这一点已通过一系列光谱学和机理实验得以阐明。首次使用这种无光催化剂的方法对线性的伯，仲和叔烷氧基进行了选择性的C（sp 3）-C（sp 3）键裂解和烯丙基化/烯基化反应。
• Iron-Catalyzed Borrowing Hydrogen β-<i>C</i>(sp³)-Methylation of Alcohols
  作者：Kurt Polidano、Jonathan M. J. Williams、Louis C. Morrill

  DOI：10.1021/acscatal.9b02461

  日期：2019.9.6

  Herein we report the iron-catalyzed beta-C(sp(3))-methylation of primary alcohols using methanol as a Cl building block. This borrowing hydrogen approach employs a well-defined bench-stable (cyclopentadienone)iron(0) carbonyl complex as precatalyst (5 mol %) and enables a diverse selection of substituted 2-arylethanols to undergo beta-C(sp(3))-methylation in good isolated yields (24 examples, 65% average yield).
• Metz, Peter; Stoelting, Joern; Laege, Mechtild, Angewandte Chemie, 1994, vol. 106, # 21, p. 2275 - 2276
  作者：Metz, Peter、Stoelting, Joern、Laege, Mechtild、Krebs, Bernt

  DOI：——

  日期：——
• Alcaide, Benito; Areces, Pilar; Borredon, Elisabeth, Heterocycles, 1990, vol. 31, # 11, p. 1997 - 2002
  作者：Alcaide, Benito、Areces, Pilar、Borredon, Elisabeth、Biurrun, Cristina、Castellas, Javier P.、Plumet, Joaquin

  DOI：——

  日期：——
• JPS5481273A
  申请人：——

  公开号：JPS5481273A

  公开（公告）日：1979-06-28

表征谱图