2-morpholino-1,4-benzoquinone | 4370-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-morpholino-1,4-benzoquinone
• 英文别名: 2-Morpholino-p-benzochinon；N-(2,5-dioxocyclohexa-1,4-dienyl)morpholine；morpholino-1,4-benzoquinone；2-morpholinocyclohexa-2,5-diene-1,4-dione；2-morpholin-4-yl-[1,4]benzoquinone；2-Morpholino-1,4-benzochinon；Morpholino-[1,4]benzochinon；2-morpholin-4-ylcyclohexa-2,5-diene-1,4-dione
• CAS: 4370-69-8
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: VNPPTLVCKNOXOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-morpholino-1,4-benzoquinone 在 palladium on activated charcoal 氢气 、 三氯化硼 、 苄基三甲基氢氧化铵 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 4.5h， 生成 N-(4-formyl-5-hydroxy-2-methoxyphenyl)morpholine
  参考文献：
  名称：

  Crossley, Roger; Goolamali, Zia; Gosper, Jeffrey J., Journal of the Chemical Society. Perkin transactions II, 1994, # 3, p. 513 - 520

  摘要：

  DOI：
• 作为产物：
  描述：

  对苯醌 、 吗啉 以 四氢呋喃 为溶剂， 反应 0.25h， 以91%的产率得到2-morpholino-1,4-benzoquinone
  参考文献：
  名称：

  Crossley, Roger; Goolamali, Zia; Gosper, Jeffrey J., Journal of the Chemical Society. Perkin transactions II, 1994, # 3, p. 513 - 520

  摘要：

  DOI：

文献信息

• A one-pot access to 2-(N-substituted Amino)-Quinones or 3-indolyl-Quinones from naphthol/hydroquinone
  作者：Yu Dong、Yong Chen、Zhan-Yuan Zhang、Jun-Hu Qian、Zhen-Zhen Peng、Bo Chang、Zhi-Chuan Shi、Zhong-Hui Li、Bing He

  DOI：10.1016/j.tet.2023.133337

  日期：2023.4

  naphthol/hydroquinone with amines or indoles, such as various (hetero)aromatic amine and aliphatic amine, has been developed. The reaction proceeds through oxidation of naphthol/hydroquinone with the CuBr2 or (NH4)2S2O8 oxidant. This reaction provides efficient access to the biologically important and synthetically useful 2-amino-quinones and 3-indolyl-quinones with good yields under mild conditions. The present

  从萘酚/氢醌与胺或吲哚，如各种（杂）芳胺和脂肪胺，到2-（ N-取代氨基）-1,4-醌或 3-吲哚基醌的顺序一锅法已经发达。该反应通过使用CuBr 2或(NH 4 ) 2 S 2 O 8氧化剂氧化萘酚/氢醌来进行。该反应提供了在温和条件下以良好的产率有效地获得生物学上重要且合成有用的 2-氨基醌和 3-吲哚基醌。本协议简单、实用，并显示出良好的功能组耐受性。
• Untersuchungen �ber Chinone, 10. Mitt. Zur Reaktion vonp-Benzochinon mit sekund�ren aliphatischen Aminen
  作者：R. Ott、E. Pinter

  DOI：10.1007/bf00807099

  日期：——

  p-Benzoquinone (1) reacts with dialkylamines 2a-d to 2-dialkylamino-p-benzoquinones 3, 2,5-bis-dialkylamino-p-benzoquinones 4, 2-dialkylamino-8-hydroxydibenzofuran-1,4-quinones 5, and in pyridine also to 2-dialkylamino-5-p-hydroxy-phenoxy-p-benzoquinones 6. A method affording almost exclusively 3 has been developed which is also applicable to compounds 2e-h.
• Green protocol for conjugate addition of amines to p-quinones accelerated by water
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、Tallapally Swamy、Kattela Shiva Shankar

  DOI：10.1007/s00706-008-0917-1

  日期：2008.11

  Amines undergo smooth conjugate addition to p-quinones in H2O at ambient temperature in the absence of a catalyst to produce 2-aminoquinones in excellent yields. Significant rate acceleration of this reaction is observed in H2O compared to organic solvents. H2O played a dual role in simultaneously activating the p-quinone and amine. This new methodology constitutes an easy, highly efficient, and green synthesis of substituted p-quinones.
• Henry; Smith, Journal of the American Chemical Society, 1952, vol. 74, p. 278
  作者：Henry、Smith

  DOI：——

  日期：——
• Domino [4 + 2] Annulation Access to Quinone–Indolizine Hybrids: Anticancer <i>N</i>-Fused Polycycles
  作者：Dirgha Raj Joshi、Yohan Seo、Yunkyung Heo、So-hyeon Park、Yechan Lee、Wan Namkung、Ikyon Kim

  DOI：10.1021/acs.joc.0c01291

  日期：2020.8.21

  A highly efficient synthetic route to new quinone-indolizine hybrids was accomplished from quinones and N-substituted pyrrole-2-carboxaldehydes via a domino Michael addition-aldol condensation-aromatization sequence through which the central pyridine ring was constructed in atom-economical and environment-friendly manner. Post modification of the resulting products was also demonstrated, enabling further expansion of this heterocyclic chemical space. Biological evaluation of the quinone-indolizine hybrids revealed potent anticancer effects in human prostate adenocarcinoma cells (PC-3) and oral adenosquamous carcinoma cells (CAL-27).