2-(Furan-2-yl)-1,4,5,6-tetrahydropyrimidine | 1307747-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(Furan-2-yl)-1,4,5,6-tetrahydropyrimidine
• 英文别名: 2-(furan-2-yl)-1,4,5,6-tetrahydropyrimidine
• CAS: 1307747-65-4
• 化学式: C₈H₁₀N₂O
• 分子量: 150.18
• InChiKey: DLEDWSBIBUGHPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.5
• 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)-1,4,5,6-tetrahydropyrimidine 在 吡啶 、 sodium hydroxide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 2-(2-呋喃基)嘧啶
  参考文献：
  名称：

  Efficient and Benign One-Pot Conversion of N-Tosyl-1,4,5,6-tetrahydropyrimidines to Pyrimidines via Tandem β-Elimination and Aromatization

  摘要：

  An efficient, mild, benign, and practical method for one-pot conversion of N-tosyl-1,4,5,6-tetrahydropyrimidines into pyrimidines is discussed in detail. In this method, N-tosyl-1,4,5,6-tetrahydropyrimidines are first prepared via N-tosylation of tetrahydropyrimidines with TsCl and then treated with 1.5 equivalents of NaOH in dimethylsulfoxide (DMSO) under air at 60 degrees C to afford corresponding pyrimidines in 70-95% yields via cascade -elimination and aromatization. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resources: Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.764433
• 作为产物：
  描述：

  2-氰基呋喃 、 1,3-丙二胺 在 Montmorillonite K-10 作用下， 反应 5.0h， 以95%的产率得到2-(Furan-2-yl)-1,4,5,6-tetrahydropyrimidine
  参考文献：
  名称：

  A green and selective synthesis of 2-aryloxazines and 2-aryltetrahydropyrimidines

  摘要：

  AbstractAn efficient method for the selective synthesis of 2‐substituted oxazines and tetrahydropyrimidines by the reaction of arylnitriles with 3‐amino‐1‐propanol and 1,3‐diaminopropane in the presence of montmorillonite K‐10 and KSF as inexpensive, environmentally benign, and reusable catalysts under classical heating conditions and microwave irradiation is reported. J. Heterocyclic Chem., (2011).

  DOI：

  10.1002/jhet.557

文献信息

• A green and selective synthesis of 2-aryloxazines and 2-aryltetrahydropyrimidines
  作者：Iraj Mohammadpoor-Baltork、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani、Zohre Eskandari

  DOI：10.1002/jhet.557

  日期：2011.3

  AbstractAn efficient method for the selective synthesis of 2‐substituted oxazines and tetrahydropyrimidines by the reaction of arylnitriles with 3‐amino‐1‐propanol and 1,3‐diaminopropane in the presence of montmorillonite K‐10 and KSF as inexpensive, environmentally benign, and reusable catalysts under classical heating conditions and microwave irradiation is reported. J. Heterocyclic Chem., (2011).
• Efficient and Benign One-Pot Conversion of <i>N</i>-Tosyl-1,4,5,6-tetrahydropyrimidines to Pyrimidines via Tandem <font>β</font>-Elimination and Aromatization
  作者：Tien Ha Trieu、Jing Dong、Xiao-Xin Shi、Xia Lu、Qiang Zhang

  DOI：10.1080/00397911.2013.764433

  日期：2013.12.2

  An efficient, mild, benign, and practical method for one-pot conversion of N-tosyl-1,4,5,6-tetrahydropyrimidines into pyrimidines is discussed in detail. In this method, N-tosyl-1,4,5,6-tetrahydropyrimidines are first prepared via N-tosylation of tetrahydropyrimidines with TsCl and then treated with 1.5 equivalents of NaOH in dimethylsulfoxide (DMSO) under air at 60 degrees C to afford corresponding pyrimidines in 70-95% yields via cascade -elimination and aromatization. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resources: Full experimental and spectral details.]