2-isobutyl-4-furanmethanol | 76656-64-9

• 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-isobutyl-4-furanmethanol
• 英文别名: 2-isobutyl-4-hydroxymethylfuran；(5-isobutylfuran-3-yl)methanol；(5-Isobutyl-3-furyl)methanol；[5-(2-methylpropyl)furan-3-yl]methanol
• CAS: 76656-64-9
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: DKJSPZPYGKPVHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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-isobutyl-4-furanmethanol 在 吡啶 、 氯化亚砜 作用下， 以 乙醚 、 苯 为溶剂， 反应 20.0h， 生成 2-isobutyl-4-(diethoxyphosphorylmethyl)furan
  参考文献：
  名称：

  Synthesis and aminomethylation of 2-isobutyl-3-and 4-diethoxyphosphorylmethylfurans

  摘要：

  Synthetic procedure for preparing 2-isobutyl-3- and 4-furancarboxylic acyl chlorides is developed. Reduction of these compounds with lithium alumohydride leads to corresponding alcohols which under treating with thionyl chloride in the presence of pyridine form chloromethyl derivatives. The latter compounds are phosphorylated with sodium diethyl phosphite under the Michaelis-Becker reaction conditions to give corresponding phosphonates. Reaction of compounds obtained with dimethyl(chloromethyl)amine proceeds at the free alpha-position of the furan ring and delivers aminophosphonates. These substances do not evolve dimethylamine even under the conditions of vacuum distillation (145-150 degrees C, 1 mm Hg).

  DOI：

  10.1134/s1070363206070103
• 作为产物：
  描述：

  2-(2-Isobutyl-[1,3]dioxolan-2-ylmethyl)-2-nitro-propane-1,3-diol 在 碳酸氢钠 、 溶剂黄146 作用下， 生成 2-isobutyl-4-furanmethanol
  参考文献：
  名称：

  Escalona, H.; Maldonado, L.A., Synthetic Communications, 1980, vol. 10, # 11, p. 857 - 862

  摘要：

  DOI：

文献信息

• Rapid Access to 3-Acyl-5-alkoxybutyrolactams Using Triplet and Singlet Oxygen
  作者：Manolis Sofiadis、John Sarris、Tamsyn Montagnon、Dimitris Kalaitzakis、Georgios Vassilikogiannakis

  DOI：10.1002/ejoc.201800832

  日期：2018.9.9

  furans has been developed. The operationally simple one‐pot method is initiated by singlet oxygen, but also later uses ground state oxygen (triplet oxygen) and is dependent on methylene blue which acts in a dual role; first as a sensitizer and then as a radical initiator in the dark.

  已开发出一种新的高效方法，该方法可从易于获得的呋喃中合成3酰基5烷氧基丁内酰胺单元。操作简单的单锅法由单线态氧引发，但后来也使用基态氧（三重态氧），并依赖于具有双重作用的亚甲基蓝。首先作为敏化剂，然后作为黑暗中的自由基引发剂。
• A simple approach to 2-substituted-4-furanmethanol compounds
  作者：Reyna Díaz-Cortés、Ana L. Silva、Luis A. Maldonado

  DOI：10.1016/s0040-4039(97)00339-0

  日期：1997.3

  A two step synthesis of the title compounds from easily available starting materials is reported. The method involves a Horner-Wadsworth-Emmons reaction between beta-ketophosphonates and 1,3-diacetoxy-2-propanone, followed by mild acid treatment of the gamma,gamma'-diacetoxyenones thus obtained. (C) 1997 Elsevier Science Ltd.
• Synthesis and aminomethylation of 2-isobutyl-3-and 4-diethoxyphosphorylmethylfurans
  作者：L. M. Pevzner

  DOI：10.1134/s1070363206070103

  日期：2006.7

  Synthetic procedure for preparing 2-isobutyl-3- and 4-furancarboxylic acyl chlorides is developed. Reduction of these compounds with lithium alumohydride leads to corresponding alcohols which under treating with thionyl chloride in the presence of pyridine form chloromethyl derivatives. The latter compounds are phosphorylated with sodium diethyl phosphite under the Michaelis-Becker reaction conditions to give corresponding phosphonates. Reaction of compounds obtained with dimethyl(chloromethyl)amine proceeds at the free alpha-position of the furan ring and delivers aminophosphonates. These substances do not evolve dimethylamine even under the conditions of vacuum distillation (145-150 degrees C, 1 mm Hg).
• Escalona, H.; Maldonado, L.A., Synthetic Communications, 1980, vol. 10, # 11, p. 857 - 862
  作者：Escalona, H.、Maldonado, L.A.

  DOI：——

  日期：——