3-(cyclohex-2-en-1-yl)-4-hydroxy-2H-chromen-2-one | 109797-45-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(cyclohex-2-en-1-yl)-4-hydroxy-2H-chromen-2-one
• 英文别名: 3-Cyclohex-2-en-1-yl-4-hydroxychromen-2-one；3-cyclohex-2-en-1-yl-4-hydroxychromen-2-one
• CAS: 109797-45-7
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: KFLWYPCKDPJMKR-UHFFFAOYSA-N

物化性质

• 沸点：
  430.1±45.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(cyclohex-2-en-1-yl)-4-hydroxy-2H-chromen-2-one 在 pyridinium hydrobromide perbromide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以94%的产率得到3-Bromo-3-(2,3-dibromo-cyclohexyl)-chroman-2,4-dione
  参考文献：
  名称：

  N-Iodosuccinimide mediated regioselective heterocyclization of 3-cyclohex-2′-enyl-4-hydroxycoumarin

  摘要：

  A number of 3-cyclohex-2'-enyl-4-hydroxy[1]benzopyran-2-ones are regioselectively cyclized by treatment with N-iodosuccinimide in acetonitrile to afford 9'-iodo-2'-oxabicyclo[3,3,I]nonano[4',3'-c][I]benzopyran-2-ones in excellent yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01024-4
• 作为产物：
  描述：

  4-羟基香豆素 在 potassium carbonate 作用下， 以 氯苯 、 丙酮 为溶剂， 反应 25.0h， 生成 3-(cyclohex-2-en-1-yl)-4-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  Majumdar, K C; Khan, A T; Gupta, A K, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 10, p. 667 - 672

  摘要：

  DOI：

文献信息

• Ionic Liquids with Multi‐Active Sites Synergistically Catalyzed Metal‐Free Transformation of Alcohols Using Dimethyl Carbonate as an Environmental Solvent
  作者：Zengmin Li、Yating Wen、Ning Wang、Feng Han、Ying Li、Hongfeng Zhuang、Chengxia Miao

  DOI：10.1002/ejoc.202100564

  日期：2021.7.22

  Pyridine-based ionic liquids with multiple active sites synergistically catalyzed C3 substitution of 4-hydroxycoumarin with alcohols in dimethyl carbonate was demonstrated. The system was efficient, economic and environmental and successfully applied for the synthesis of coumatetralyl as commercial rodenticide. And a mechanism involving a SN1 pathway, synergistically promoted effect of hydrogen bonding

  证明了具有多个活性位点的吡啶基离子液体在碳酸二甲酯中协同催化 4-羟基香豆素与醇的 C3 取代。该系统高效、经济、环保，成功应用于合成香豆四烯基作为商业杀鼠剂。和涉及S上机构Ñ 1途径的氢键，碳正离子和醚协同促进效果，提出了。
• Acid-Catalyzed Regiodivergent Annulation of 4-Hydroxycoumarins with Isoprene: Entry to Pyranocoumarins and Pyranochromones
  作者：Ying Li、Yan-Cheng Hu、Hao Zheng、Ding-Wei Ji、Yu-Feng Cong、Qing-An Chen

  DOI：10.1002/ejoc.201901154

  日期：2019.10.17

  An acid‐catalyzed regiodivergent annulation of biomass‐derived 4‐hydroxycoumarins with isoprene is developed, providing a facile access to pyranocoumarins and pyranochromones.

  开发了一种酸催化的生物质衍生的4-羟基香豆素与异戊二烯的区域发散环化反应，可轻松获得吡喃香豆素和吡喃色酮。
• Direct Catalytic Benzylation of Hydroxycoumarin - Efficient Synthesis of Warfarin Derivatives and Analogues
  作者：Magnus Rueping、Boris Nachtsheim、Erli Sugiono

  DOI：10.1055/s-0029-1219936

  日期：2010.6

  Effective metal-catalyzed benzylations of 4-hydroxycoumarin have been developed. Employing a low amount of a cheap, nontoxic, and air-stable catalyst the 3-alkylated hydroxycoumarins were isolated in high yields after short reaction times. Applying this new methodology two widely used anticoagulants phenprocoumon and coumatetralyl were synthesized applying mild reaction conditions.

  已经开发出有效的金属催化4-羟基香豆素苄基化反应。使用少量廉价、无毒且稳定的催化剂，经过短时间反应后，获得了高产率的3-烷基化羟基香豆素。采用这种新方法，合成了两种广泛使用的抗凝剂苯普鲁孔和氟克洛络。
• Rhodium(II)-catalyzed reactions of 3-diazo-2,4-chromenediones. First one-step synthesis of pterophyllin 2
  作者：Yong Rok Lee、Jung Yup Suk、Byung So Kim

  DOI：10.1016/s0040-4039(99)01317-9

  日期：1999.9

  described. Reactions of 1 with nitriles, isocyanates, and ketones give the corresponding 5-membered heterocycles in moderate yields, whereas those of 1 with acid chlorides afford α-chloroenones in moderate yields. Reactions of 1 with electron-rich and -deficient olefins such as vinyl ethers and allyl iodide give dihydrofurocoumarins as a single compound, whereas those of 3 with vinyl esters afford either angular

  本文描述了铑（II）催化的3-重氮-2,4-氧化铬1-3与各种底物的反应。的反应1与腈类，异氰酸酯，和酮，得到相应的5-元杂环在中等产率，而那些的1与酰氯得到α-chloroenones在中等产率。的反应1与富电子和缺陷型的烯烃如乙烯基醚和烯丙基碘给予dihydrofurocoumarins作为单一化合物，而那些的3与乙烯基酯得到任一角度dihydrofurocoumarin和线性产物或重排的产物，为异构体。此外，该新方法已应用于合成自叶绿素2分离的天然pterophyllin 2。翼状叶蕨。
• Patra, Amarendra; Mukhopadhyay, Apurba K.; Mitra, Alok K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 1167 - 1170
  作者：Patra, Amarendra、Mukhopadhyay, Apurba K.、Mitra, Alok K.

  DOI：——

  日期：——