3-phenyl-5-(pyridin-3-yl)isoxazole | 85903-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-phenyl-5-(pyridin-3-yl)isoxazole
• 英文别名: 5-(pyridin-3-yl)-3-phenylisoxazole；3-(3-phenylisoxazol-5-yl)pyridine；3-(3-phenyl-isoxazol-5-yl)-pyridine；3-Phenyl-5-<β-pyridyl>-isoxazol；3-Phenyl-5-α-pyridyl-isoxazol；3-Phenyl-5-β-pyridyl-isoxazol；3-phenyl-5-pyridin-3-yl-1,2-oxazole
• CAS: 85903-34-0
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: REEGLRDTPSFUGV-UHFFFAOYSA-N

物化性质

• 熔点：
  145-146 °C(Solv: ligroine (8032-32-4))
• 沸点：
  420.5±30.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-2-(benzotriazol-1-yl)-1-phenyl-3-(3-pyridinyl)-2-propen-1-one 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 以81%的产率得到3-phenyl-5-(pyridin-3-yl)isoxazole
  参考文献：
  名称：

  区域选择性合成多取代的吡唑和异恶唑。

  摘要：

  已经开发了区域选择性合成方法，用于制备不对称的1,3,5-三芳基-4-烷基吡唑啉和-吡唑，方法是用单取代的肼处理α-苯并三唑基-α，β-不饱和酮，然后在4位上烷基化吡唑啉环。α-苯并三唑基-α，β-不饱和酮与羟胺反应，可选择性地3，5-二取代的异恶唑。

  DOI：

  10.1021/jo0101407

文献信息

• Simple and Highly Efficient Synthesis of 3,5-Disubstituted Isoxazoles Using Cu/Graphene/Clay Nanohybrid as a New Heterogeneous Nano Catalyst
  作者：Somayeh Behrouz、Mohammad Navid Soltani Rad

  DOI：10.3184/174751915x14452715274657

  日期：2015.12

  nanohybrid) as a highly efficient heterogeneous nano-catalyst is described. In this method, Cu/AC/r-GO nanohybrid catalyses the 1,3-dipolar cycloaddition of alkynes and nitrile oxides in the presence of NaHCO3 in H2O/THF (50:50, V/V) to afford the corresponding 3,5-disubstituted isoxazoles. The Cu/AC/r-GO nanohybrid is a low cost, non-hygroscopic, chemically and thermally stable catalyst that can be reused

  描述了一种简单方便的协议，用于结构多样的炔烃与原位生成的腈氧化物的“点击”环加成反应，由 Cu/氨基粘土/还原氧化石墨烯纳米杂化物（Cu/AC/r-GO 纳米杂化物）作为一种高效的异质纳米催化剂。 . 在该方法中，Cu/AC/r-GO 纳米杂化物在 H2O/THF (50:50, V/V) 中 NaHCO3 存在下催化炔烃和腈氧化物的 1,3-偶极环加成反应，得到相应的 3,5 -二取代的异恶唑。Cu/AC/r-GO 纳米杂化物是一种低成本、不吸湿、化学和热稳定的催化剂，可重复用于许多连续的反应运行，而不会显着降低其反应性。
• Facile consecutive three-component synthesis of 3,5-disubstituted isoxazoles
  作者：Christina Görgen、Thomas J. J. Müller

  DOI：10.1007/s10593-017-2069-x

  日期：2017.4

  3,5-Di(hetero)aryl-substituted isoxazoles can be rapidly synthesized in a one-pot fashion by a consecutive three-component alkynylation–cyclization sequence starting from (hetero)aroyl chloride, alkynes, and sodium azide/acetic acid under copper-free palladium catalysis as exemplified by 9 different products.

  3,5-二（杂）芳基取代的异恶唑可以通过一锅法通过连续的三组分炔基化-环化顺序快速合成，该顺序从铜下的（杂）芳酰氯，炔烃和叠氮化钠/乙酸开始无钯催化，如9种不同产品所示。
• A direct access to isoxazoles from ynones using trimethylsilyl azide as amino surrogate under metal/catalyst free conditions
  作者：Gadi Ranjith Kumar、Yalla Kiran Kumar、Maddi Sridhar Reddy

  DOI：10.1039/c6cc02047j

  日期：——

  A general access to isoxazoles with outstanding functional group compatibility from the readily available ynones using trimethylsilyl azide as an amino surrogate under exceptionally simple conditions is described.

  描述了一种从易得的炔酮中使用三甲基硅基叠氮作为氨代用体，在异常简单的条件下获得异噁唑并具有出色的官能团兼容性的一般方法。
• Cyclocondensation of Hydroxylamine with 1,3-Bis(het)arylmonothio 1,3-Diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-prop­enones: Synthesis of 3,5-Bis(het)arylisoxazoles with Complementary Regioselectivity
  作者：Byregowda Raghava、Gangajji Parameshwarappa、Anand Acharya、Toreshettahally R. Swaroop、Kanchugarakoppal S. Rangappa、Hiriyakkanavar Ila

  DOI：10.1002/ejoc.201301667

  日期：2014.3

  monothio-substituted 1,3-diketones is installed at the 3-position. On the other hand, the reaction of hydroxylamine hydrochloride with 3-(methylthio)-1,3-bis(het)aryl-2-propenones 2 in the presence of barium hydroxide in refluxing ethanol gave 3,5-bis(het)arylisoxazoles 6 with complementary regioselectivity in high yields. A probable mechanism for the formation of regioisomeric isoxazoles 5 and 6 from precursors

  已经开发了区域选择性合成具有互补区域选择性的 3,5-双（杂）芳基异恶唑的有效途径。该方法包括盐酸羟胺与 1,3-双（杂）芳基-单硫代取代的 1,3-二酮 1 或与 3-甲硫基-1,3-双（杂）芳基-2-丙烯酮 2 在各种反应条件。在第一个方案中，在醋酸钠/醋酸（pH 2.2）的存在下，在回流的乙醇/苯中用盐酸羟胺处理二酮 1，得到 3,5-双（杂）芳基异恶唑 5，其中杂（芳基）与单硫代取代的 1,3-二酮的硫代羰基相连的部分位于 3-位。另一方面，盐酸羟胺与3-(甲硫基)-1反应，3-双(杂)芳基-2-丙烯酮2在氢氧化钡存在下在回流乙醇中以高产率得到具有互补区域选择性的3,5-双(杂)芳基异恶唑6。已经提出了由前体 1 和 2 形成区域异构异恶唑 5 和 6 的可能机制。
• Regioselective Synthesis and Slow-Release Suzuki–Miyaura Cross-Coupling of MIDA Boronate-Functionalized Isoxazoles and Triazoles
  作者：Jonathan E. Grob、Jill Nunez、Michael A. Dechantsreiter、Lawrence G. Hamann

  DOI：10.1021/jo201973t

  日期：2011.12.16

  The efficient preparation of heterocycles with a range of substitutions ortho to heteroatoms remains as a challenge in organic synthesis, particularly relevant to the construction of druglike molecules due to the ubiquitous presence of such moieties in that chemical space. Modular installation of heterocyclic building blocks using Suzuki-Miyaura cross-coupling is a conceptually useful strategy to address this challenge, though this has historically been met with technical difficulty due to issues of inaccessibility and instability of the requisite heterocyclic boronates. Herein we report a mild and highly regioselective cycloaddition approach which affords convenient access to stable MLDA boronate-functionalized isoxazoles and triazoles and their subsequent efficient Suzuki-Miyaura cross-coupling. This methodology is then further applied to a set of druglike compounds in an efficient one-pot telescoped sequence in line with green chemistry principles.