2-methyl-3,5-diphenyl-2,3-dihydro-1,2-oxazole | 52266-12-3

• 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-methyl-3,5-diphenyl-2,3-dihydro-1,2-oxazole
• 英文别名: 2-methyl-3,5-diphenyl-2,3-dihydroisoxazole；3,5-Diphenyl-2-methyl-4-isoxazoline；2-methyl-3,5-diphenyl-2,3-dihydro-isoxazole；2-Methyl-3,5-diphenyl-4-isoxazolin；2-methyl-3,5-diphenyl-3H-1,2-oxazole
• CAS: 52266-12-3
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: YETJIADJZFBWEP-UHFFFAOYSA-N

物化性质

• 熔点：
  81 °C(Solv: hexane (110-54-3))
• 沸点：
  365.4±52.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-3,5-diphenyl-2,3-dihydro-1,2-oxazole 在 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.17h， 生成 (2E)-3-(dimethylamino)-1,3-diphenylprop-2-en-1-one
  参考文献：
  名称：

  One-Pot Oxidation and Rearrangement of Propargylamines and in Situ Pyrazole Synthesis

  摘要：

  Reported here are procedures for a one-pot oxidation and rearrangement of propargylamines to synthesize enaminones, with supporting mechanistic studies. Also reported are the extended one-pot syntheses of pyrazoles, including celecoxib and various heterocyclic compounds.

  DOI：

  10.1021/ol501842b
• 作为产物：
  描述：

  2-methyl-3,5-diphenyl-isoxazolium; methyl sulfate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以75%的产率得到2-methyl-3,5-diphenyl-2,3-dihydro-1,2-oxazole
  参考文献：
  名称：

  Synthesis of 4-Isoxazolines by Reduction ofN-Methylisoxazolium Salts with Complex Metal Hydrides

  摘要：

  DOI：

  10.1055/s-1982-30069

文献信息

• Iridium-Catalyzed Cyclization of Isoxazolines and Alkenes: Divergent Access to Pyrrolidines, Pyrroles, and Carbazoles
  作者：Zu-Feng Xiao、Ting-Hui Ding、Sheng-Wei Mao、Zaher Shah、Xiao-Shan Ning、Yan-Biao Kang

  DOI：10.1021/acs.orglett.6b02905

  日期：2016.11.4

  iridium-complex-catalyzed N–O-cleaving rearrangement/cyclization of 2,3-dihydroisoxazoles with alkenes has been developed. It provides divergent access to multiple substituted pyrrolidines, pyrroles, and carbazoles. The iridium catalyst remains highly catalytic active after seven cycles. The gram-scale synthesis afforded a carbazole with strong bluish-violet fluorescence.

  已经开发了异质铱络合物催化的2，3-二氢异恶唑与烯烃的N-O裂解重排/环化反应。它提供了多种取代基，分别取代了吡咯烷，吡咯和咔唑。铱催化剂在七个循环后仍保持高催化活性。克级合成得到咔唑，具有强烈的蓝紫色荧光。
• Zinc Iodide-Mediated Direct Synthesis of 2,3-Dihydroisoxazoles from Alkynes and Nitrones
  作者：Zu-Feng Xiao、Ting-Hui Ding、Sheng-Wei Mao、Xiao-Shan Ning、Yan-Biao Kang

  DOI：10.1002/adsc.201600044

  日期：2016.6.2

  A zinc diiodide (ZnI2)‐mediated direct synthesis of 2,3‐dihydroisoxazoles via a [3+2] cycloaddition reaction of the nitrones and non‐electron‐deficient terminal alkynes has been developed. This method was applied in the formal synthesis of HPA‐12 and aminoglucose.

  甲二碘化锌（ZnI 2）介导的2,3- dihydroisoxazoles直接合成经由所述硝酮和非缺电子末端炔烃的[3 + 2]环加成反应得到了发展。该方法用于HPA-12和氨基葡萄糖的正式合成。
• Synthesis of Highly Functionalized Indoles and Indolones via Selectivity-Switchable Olefinations
  作者：Ting-Hui Ding、Zu-Feng Xiao、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/acs.joc.7b03158

  日期：2018.2.16

  Highly functionalized indoles and indolones were prepared via selectivity-switchable mono- or diolefinations. The Julia olefination of the products followed by a Brønsted acid-prompted cyclization afforded indolones, whereas the indoles were obtained by a sequential Wittig olefination and electrocyclization. This method opens divergent access to highly functionalized nitrogen-containing bicyclic or

  高度官能化的吲哚和吲哚酮是通过选择性可切换的单烯烃或二烯烃制备的。产物的茱莉亚烯化，然后进行布朗斯台德酸促进的环化，得到了吲哚酮，而吲哚是通过连续的维蒂希烯化和电环化获得的。该方法使对高度官能化的含氮双环或三环杂环的分歧开放。
• 一种多取代2,3-二氢异噁唑类化合物的合成 方法
  申请人：湖北科技学院

  公开号：CN106986840B

  公开（公告）日：2019-08-20

  本发明提供了一种多取代2,3‑二氢异噁唑类化合物的合成方法，该方法以炔类化合物与取代硝酮为原料，在碱性环境中温和的条件下合成多取代2,3‑二氢异噁唑化合物。该方法具有无过渡金属催化剂、原料廉价易得、反应底物适应性广、反应条件温和、区位选择性好、产率高、绿色环保等优点。
• Isoxazoles. XXII. A New Synthesis of 4-Isoxazolines and Their Thermal Conversion into Pyrroles
  作者：IKUO ADACHI、KIMIKO HARADA、RIE MIYAZAKI、HIDEO KANO

  DOI：10.1248/cpb.22.61

  日期：——

  Thirteen N-substituted 4-isoxazoline derivatives were obtained by reaction of 3-unsubstituted and 3, 5-disubstituted isoxazolium salts with Grignard reagents. Similarly, 3-benzyl-2-methyl-2, 3, 4, 5-tetrahydronaphth [2, 1-d] isoxazoles and 3-benzyl-2-ethyl-2, 3-dihydrobenzisoxazole were produced by reaction of the corresponding quaternary salts with benzylmagnesium chloride. Thermal reactions of some 4-isoxazoline derivatives and 3-benzyl-2, 3, 4, 5-tetrahydronaphth [2, 1-d] isoxazole derivatives leading to substituted pyrrole derivatives and 3H-benz [e] indole derivatives were investigated. A tentative mechanism for the formation of pyrrole from 4-isoxazoline is also presented.

  通过 3-未取代和 3，5-二取代的异噁唑鎓盐与格氏试剂反应，得到了 13 种 N-取代的 4-异噁唑啉衍生物。同样，相应的季盐与苄基氯化镁反应生成了 3-苄基-2-甲基-2，3，4，5-四氢萘[2，1-d]异噁唑和 3-苄基-2-乙基-2，3-二氢苯并异噁唑。研究了一些 4-异噁唑啉衍生物和 3-苄基-2，3，4，5-四氢萘[2，1-d]异噁唑衍生物的热反应，这些反应生成了取代的吡咯衍生物和 3H 苯并[e]吲哚衍生物。此外，还提出了由 4-isoxazoline 生成吡咯的初步机理。