2-(4-bromophenyl)-5,6-dihydro-4H-1,3-oxazine | 62460-59-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-bromophenyl)-5,6-dihydro-4H-1,3-oxazine
• CAS: 62460-59-7
• 化学式: C₁₀H₁₀BrNO
• 分子量: 240.099
• InChiKey: JTUMUVTWUSWRPB-UHFFFAOYSA-N

物化性质

• 熔点：
  73-75 °C
• 沸点：
  318.3±25.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴苯腈 、 3-氨基-1-丙醇 在 phosphotungstic acid 作用下， 反应 2.08h， 以96%的产率得到2-(4-bromophenyl)-5,6-dihydro-4H-1,3-oxazine
  参考文献：
  名称：

  H₃PW₁₂O₄₀: An Efficient and Recyclable Heterogeneous Catalyst for the Selective Synthesis of 2-Aryl-5,6-dihydro-4H-1,3-oxazines and 2-Aryl-1,4,5,6-tetrahydropyrimidines

  摘要：

  已开发出一种环保且高效的程序，可通过芳基腈与3-氨基-1-丙醇和1,3-二氨基丙烷在热条件和微波辐射下，在催化剂H₃PW₁₂O₄₀的存在下，选择性合成2-芳基-5,6-二氢-4H-1,3-噁嗪和2-芳基-1,4,5,6-四氢嘧啶。在相同的反应条件下，二氰基苯可以转化为相应的单噁嗪和单四氢嘧啶，具有优异的化学选择性。这些反应简单干净，产物收率高，纯度高。催化剂在反应后可以轻松回收并在后续运行中有效地重复使用。

  DOI：

  10.1515/znb-2010-0404

文献信息

• S–Co(II) cascade catalysis: cyclocondensation of aromatic nitriles with alkamine
  作者：Haixia Ge、Ping Liu、Xiangnan Li、Wei Sun、Jianli Li、Bingqin Yang、Zhen Shi

  DOI：10.1016/j.tet.2013.05.132

  日期：2013.8

  A solvent-free S/Co(NO3)2 cascade catalyzed cyclocondensation reaction of aromatic nitriles with 3-amino-1-propanol or 2-aminoethanol has been successfully developed under thermal and microwave conditions. By this two-component protocol, mono- and bis-oxazines and oxazolines were selectively synthesized both in good to excellent yields and short reaction times. This catalytic system exhibits excellent

  在热和微波条件下，已成功开发了无溶剂的S / Co（NO 3）2芳族腈与3-氨基-1-丙醇或2-氨基乙醇的级联催化环缩合反应。通过这种两组分方案，可以以良好至极佳的收率和较短的反应时间选择性地合成单-和双-恶嗪和恶唑啉。该催化系统具有出色的化学选择性，可以重复使用至少7次，而不会在后续反应中显着降低活性。
• Ultrasound promoted selective synthesis of 2-aryl-5,6-dihydro-4H-1,3-oxazines catalyzed by K-10 and KSF montmorillonite clays: A practical procedure under mild and solvent-free conditions
  作者：Iraj Mohammadpoor-Baltork、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani、Zohre Eskandari

  DOI：10.1016/j.ultsonch.2010.02.005

  日期：2010.6

  Montmorillonite K-10 and KSF were found to be highly efficient, environmentally friendly and recyclable heterogeneous catalysts for the selective synthesis of a variety of 2-aryl-5,6-dihydro-4H-1,3-oxazines from arylnitriles and 3-amino-1-propanol under ultrasound irradiation. This new methodology provides excellent yields in short reaction times (10-25 min). The reaction work-up is very simple and

  发现蒙脱石K-10和KSF是高效，环保和可回收的多相催化剂，用于从芳腈和3-氨基选择性合成各种2-芳基-5,6-二氢-4H-1,3-恶嗪-1-丙醇在超声照射下。这种新方法可在较短的反应时间（10-25分钟）内提供出色的产率。反应后处理非常简单，催化剂可以轻松地从反应混合物中分离出来，并在随后的反应中重复使用几次。从二腈合成单恶嗪时，该催化体系还具有出色的化学选择性。
• 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).
• Synthesis of 2-Aryl/Heteroaryloxazolines from Nitriles under Metal- and Catalyst-Free Conditions and Evaluation of Their Antioxidant Activities
  作者：Parul Garg、Shweta Chaudhary、Marilyn D. Milton

  DOI：10.1021/jo501430p

  日期：2014.9.19

  The synthesis of structurally diverse 2-aryl/heteroaryloxazolines from nitriles and aminoalcohols has been achieved under metal- and catalyst-free conditions in good to excellent yields. An array of functional groups are well-tolerated, thus, allowing the introduction of many important biologically active motifs such as azoles, ring-fused azoles, saturated heterocyclics, and amines in 2-aryloxazoline scaffolds. An evaluation of the antioxidant properties using the DPPH (diphenyl picryl hydrazyl) assay method shows the pyrrole-functionalized 2-aryloxazoline to be the best antioxidant among all the synthesized 2-aryl/heteroaryloxazolines.
• Eckstein,Z. et al., Roczniki Chemii, 1962, vol. 36, p. 73 - 85
  作者：Eckstein,Z. et al.

  DOI：——

  日期：——