2-(4-methylphenyl)-phenanthro<9,10-d>oxazole | 4414-93-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2-(4-methylphenyl)-phenanthro<9,10-d>oxazole
• 英文别名: 2-(4-methylphenyl)phenanthro<9,10-d>oxazole；2-(p-Methylphenyl)phenanthro<9,10-d>oxazole；2-(p-tolyl)phenanthro[9,10-d][1,3]oxazole；2-p-tolylphenanthro[9,10-d]oxazole；2-p-tolyl-phenanthro[9,10-d]oxazole；2-(4-Methyl-phenyl)-phenanthroxazol；2-(4-methylphenyl)phenanthro[9,10-d][1,3]oxazole
• CAS: 4414-93-1
• 化学式: C₂₂H₁₅NO
• 分子量: 309.367
• InChiKey: KPUKAYQICYIHIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  10-imino-10H-phenanthren-9-one 、 对二甲苯 生成 2-(4-methylphenyl)-phenanthro<9,10-d>oxazole
  参考文献：
  名称：

  Eue photochemische, radiationschemische und thermische bildungsweisen von phenanthroxazolen

  摘要：

  DOI：

  10.1016/s0040-4039(00)90200-4

文献信息

• 1,4-Benzoxazin-2-ones, benzo[<i>d</i>]oxazoles and 2<i>H</i>-1,4-benzoxazines from the reaction of 2-(methoxyimino)benzen-1-ones with arylacetates, arylacetic acids and<i>trans-</i>stilbene
  作者：Demetrios N. Nicolaides、R. Wajih Awad、Evangelia A. Varella

  DOI：10.1002/jhet.5570330318

  日期：1996.5

  10-(Methoxyimino)phenanthrene-9-one 1 reacts thermally with the arylacetic derivatives 2(a-j) to yield the corresponding 1,4-benzoxazin-2-ones 4(a-d,f) and benzo[d]oxazoles 5(a-e,g). Similarly, reaction of the monoximes 7a, 7b with compounds 2a, 2d respectively affords 8a, 8b, while action of trans-stilbene on the monoximes 1, 7a, 7b leads to the 1,4-benzoxazines 10, 11, 13, obtained along with the

  10-（甲氧基亚氨基）菲-9-酮1下热与arylacetic衍生物进行反应2（AJ），得到相应的1,4-苯并恶嗪-2-酮4（广告，F）和苯并[ d ]恶唑-5（AE， g）。类似地，monoximes的反应7a，图7b用化合物2A，图2d分别得到图8A，8B，而动作反式对monoximes芪1，7A，7B通向1,4-苯并恶嗪10，11，13，而获得沿与相应的2-苯基恶唑5a，8a，8c和化合物12。
• The preparation of annulated 1,3-oxazoles from 1,3,2-oxazaphospholes and aldehydes
  作者：Nárcisz Bagi、Roland Stefanovszky、József Kaizer、Gábor Speier

  DOI：10.1007/s00706-015-1607-4

  日期：2016.2

  AbstractThe reactions of 2,3-dihydro-2,2,2-triphenylphenanthro[9,10-d]-1,3,2-λ5-oxazaphospholes with aromatic aldehydes lead to the corresponding 2-substituted phenanthro[9,10-d][1,3]oxazoles via an aza-Wittig reaction in good yields. Graphical abstract

  摘要2,3-二氢-2,2,2- triphenylphenanthro [9,10-的反应d ] -1,3,2-λ 5个-oxazaphospholes与芳香醛导致相应的2-取代的菲并[9,10- d ] [1,3]恶唑可通过aza-Wittig反应获得高收率。 图形概要
• DMSO promoted catalyst-free oxidative C–N/C–O couplings towards synthesis of imidazoles and oxazoles
  作者：Debasish Bera、Rajib Sarkar、Tiyasa Dhar、Pinaki Saha、Prasanta Ghosh、Chhanda Mukhopadhyay

  DOI：10.1039/d4ob00383g

  日期：——

  (DMSO)-promoted catalyst-free oxidative C–N coupling and C–O coupling under oxidant-free conditions are outlined. This protocol is operationally simple and leads to various functionalized substituted imidazoles or oxazoles in good yields. To date, a very limited number of oxidation protocols have been established, where DMSO acts solely as a catalyst or an oxidant or both. In this report, DMSO is not only used

  概述了二甲亚砜 (DMSO) 促进的无催化剂氧化 C-N 偶联和无氧化剂条件下的 C-O 偶联。该方案操作简单，并且以良好的产率产生各种官能化的取代咪唑或恶唑。迄今为止，已经建立的氧化方案数量非常有限，其中 DMSO 仅充当催化剂或氧化剂或两者兼而有之。在本报告中，DMSO不仅用作C-N/C-O偶联剂，还用作这些氧化转化所需的氧化剂。因此，我们所证明的 DMSO 促进的无催化剂偶联转化有能力引领氧化偶联领域的新维度。
• Synthesis of phenanthro[9, 10-d]oxazoles from 10-(methoxyimino)phenanthrene-9-one
  作者：Demetrios N. Nicolaides、Evangelia A. Varella、R. Wajih Awad

  DOI：10.1016/s0040-4020(01)87251-3

  日期：1993.8

  10-(Methoxyimino)phenanthren-9-one 3 easily reacts with the methyl substituted aromatics 4(a-d), as well as with alpha-bromo-p-xylene 6 and the alpha-substituted methyl derivatives 7(a-i), to afford in 5-64% yield the corresponding 2-aryl substituted phenanthro[9,10-d]oxazoles 5(a-g), most probably via a free radical reaction sequence. In several cases the unsubstituted oxazole 12 is also obtained, while reaction of compound 3 with the N-methyl substituted amines 7g and 14(ab) leads to the aminooxazoles 13 and 15(a,b) respectively.
• A convenient strategy to 2,4,5-triaryl and 2-alkyl-4,5-diaryl oxazole derivatives through silver-mediated oxidative C O cross coupling/cyclization
  作者：Rajib Sarkar、Chhanda Mukhopadhyay

  DOI：10.1016/j.tetlet.2015.04.103

  日期：2015.6

  This is a silver(I) mediated C-alpha(sp(3))-H activation of primary amines followed by oxidative C-O cross coupling/cyclization for the construction of 2,4,5-triaryl and 2-alkyl-4,5-diaryl oxazole derivatives. The protocol has been successfully utilized to synthesize the oxazole derivatives in good to excellent yields. In this oxidative coupling, the silver species after the reaction was successfully re-synthesized and reused with almost a similar activity. (C) 2015 Elsevier Ltd. All rights reserved.