2-(3-bromophenyl)-4,5-dihydrooxazole

• 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-(3-bromophenyl)-4,5-dihydrooxazole
• 英文别名: 2-(3-bromophenyl)-1,3-oxazoline；2-(3-bromophenyl)oxazoline；2-(3-Bromophenyl)-4,5-dihydro-1,3-oxazole
• 化学式: C₉H₈BrNO
• 分子量: 226.073
• InChiKey: SJJQTHCDSIMQGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-bromophenyl)-4,5-dihydrooxazole 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 以89%的产率得到间溴苯甲醛
  参考文献：
  名称：

  通过NiCl 2还原和恶唑啉水解合成芳香醛

  摘要：

  用NiCl 2 / NaBH 4还原2-芳基-恶唑啉，然后水解，得到相应的醛，收率很高。

  DOI：

  10.1016/j.tetlet.2004.07.119
• 作为产物：
  描述：

  间溴苯甲酸 在 氯化亚砜 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 39.0h， 生成 2-(3-bromophenyl)-4,5-dihydrooxazole
  参考文献：
  名称：

  Synthesis of planar chiral [2.2]paracyclophane-based bisoxazoline ligands bearing no central chirality and application to Cu-catalyzed asymmetric O–H insertion reaction

  摘要：

  C2-对称平面手性[2.2]对二氧杂环己基双噁唑啉配体在铜催化的α-重氮酯氧-氢插入反应中有效地控制不对称诱导。

  DOI：

  10.1039/c5ob00452g

文献信息

• Copper <i>N</i>-Heterocyclic Carbene Complexes As Active Catalysts for the Synthesis of 2-Substituted Oxazolines from Nitriles and Aminoalcohols
  作者：Michael Trose、Faïma Lazreg、Mathieu Lesieur、Catherine S. J. Cazin

  DOI：10.1021/acs.joc.5b01382

  日期：2015.10.16

  The reaction between nitriles and aminoalcohols to access 2-substituted oxazolines was investigated. Using copper–NHC complexes, various nitriles were successfully converted into the corresponding oxazolines, under milder and less wasteful conditions than those of previously reported methods.

  腈和氨基醇之间的反应，以访问2取代的恶唑啉进行了研究。使用铜-NHC络合物，在比以前报道的方法温和，浪费少的条件下，各种腈成功地转化为相应的恶唑啉。
• A Convenient Synthesis of Oxazolines and Imidazolines from Aromatic Aldehydes with Pyridinium Hydrobromide Perbromide in Water
  作者：Shinsei Sayama

  DOI：10.1055/s-2006-941597

  日期：2006.6

  Various 2-oxazolines were prepared from aromatic aldehydes and 2-aminoethanol with pyridinium hydrobromide per­bromide in water at room temperature. 2-Imidazolines were also obtained in good yields from aromatic aldehydes and ethylenediamine under the same reaction conditions.

  以吡啶溴氢溴化物为催化剂，室温下在水中用芳香醛和2-氨基乙醇制备了多种2-噁唑啉。在相同反应条件下，芳香醛和乙二胺也能获得较高产率的2-咪唑啉。
• Potentiation of the fosmidomycin analogue FR 900098 with substituted 2-oxazolines against Francisella novicida
  作者：Matthew D. Stephens、Nisakorn Yodsanit、Christian Melander

  DOI：10.1039/c6md00365f

  日期：——

  A library of 33 compounds was screened for potentiation of the antibiotic FR 900098 against the Francisella tularensis surrogate Francisella novicida.

  对33种化合物进行了筛选，以增强抗生素FR 900098对弗朗西斯菌属代表性菌株新弗朗西斯菌属的作用。
• Synthesis of planar chiral [2.2]paracyclophane-based bisoxazoline ligands bearing no central chirality and application to Cu-catalyzed asymmetric O–H insertion reaction
  作者：Shinji Kitagaki、Kenta Sugisaka、Chisato Mukai

  DOI：10.1039/c5ob00452g

  日期：——

  C ₂-symmetric planar chiral [2.2]paracyclophane-based bisoxazoline ligands effectively control the asymmetric induction during the Cu-catalyzed O–H insertion reaction of α-diazo esters.

  C2-对称平面手性[2.2]对二氧杂环己基双噁唑啉配体在铜催化的α-重氮酯氧-氢插入反应中有效地控制不对称诱导。
• 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.