2,2,7-trimethyl-2H-chromen-5-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,2,7-trimethyl-2H-chromen-5-ol
• 英文别名: 2,2,7-Trimethylchromen-5-ol；2,2,7-trimethylchromen-5-ol
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: BIRASKUVCMCXRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,7-trimethyl-2H-chromen-5-ol 以 苯 为溶剂， 反应 5.0h， 以47%的产率得到C₁₂H₁₄O₂
  参考文献：
  名称：

  2,2-二甲基色烯在流动中的光化学扩环促进植物毒性 Radulanin A 的全合成

  摘要：

  radulanins 是具有生物活性的联苄基天然产物，具有合成具有挑战性的 2,5-dihydro-1-benzoxepine 核心。与之前展示冗长策略的报告相比，我们展示了迄今为止最短的 radulanin A 合成，其主要特征是 2,2-二甲基色烯前体的光化学扩环反应。鉴于对这种天然产品的除草特性的生物学研究，这项工作适用于大规模制备的连续流动装置。

  DOI：

  10.1021/acs.orglett.2c01462
• 作为产物：
  描述：

  2,2,7-三甲基-2,6,7,8-四氢色烯-5-酮 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 以25%的产率得到2,2,7-trimethyl-2H-chromen-5-ol
  参考文献：
  名称：

  A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes

  摘要：

  A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ringclosure of 1-oxatrienes.

  DOI：

  10.1021/jo020688t

文献信息

• Efficient and general method for the synthesis of benzopyrans by ethylenediamine diacetate-catalyzed reactions of resorcinols with α,β-unsaturated aldehydes. One step synthesis of biologically active (±)-confluentin and (±)-daurichromenic acid
  作者：Yong Rok Lee、Jung Hyun Choi、Sang Heum Yoon

  DOI：10.1016/j.tetlet.2005.08.159

  日期：2005.10

  An efficient and general synthesis of benzopyrans is achieved by ethylenediamine diacetate-catalyzed reactions of resorcinols with α,β-unsaturated aldehydes in moderated yields. As an application of this methodology, biologically interesting confluentin, which was known to have an inhibitory effect on histamine release is synthesized in one step. Also, natural daurichromenic acid, which has highly

  通过乙二胺二乙酸酯催化间苯二酚与α，β-不饱和醛的适度收率，可实现苯并吡喃的有效和一般合成。作为该方法的一种应用，一步合成了生物学上有意义的融合蛋白，已知该蛋白对组胺的释放具有抑制作用。此外，一步法成功地合成了具有强大的抗HIV活性的天然金鸡铬酸。
• A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes
  作者：Hong C. Shen、Jiashi Wang、Kevin P. Cole、Michael J. McLaughlin、Christopher D. Morgan、Christopher J. Douglas、Richard P. Hsung、Heather A. Coverdale、Aleksey I. Gerasyuto、Juliet M. Hahn、Jia Liu、Heather M. Sklenicka、Lin-Li Wei、Luke R. Zehnder、Craig A. Zificsak

  DOI：10.1021/jo020688t

  日期：2003.3.1

  A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ringclosure of 1-oxatrienes.
• Total Synthesis of Phytotoxic Radulanin A Facilitated by the Photochemical Ring Expansion of a 2,2-Dimethylchromene in Flow
  作者：Bruce Lockett-Walters、Simon Thuillier、Emmanuel Baudouin、Bastien Nay

  DOI：10.1021/acs.orglett.2c01462

  日期：2022.6.10

  5-dihydro-1-benzoxepine core. In contrast with previous reports exhibiting lengthy strategies, we demonstrate the shortest synthesis of radulanin A to date, featuring a largely unexplored photochemical ring expansion reaction of a 2,2-dimethylchromene precursor. This work was adapted to a continuous-flow setup for larger-scale preparation, in view of biological investigations into the herbicidal properties

  radulanins 是具有生物活性的联苄基天然产物，具有合成具有挑战性的 2,5-dihydro-1-benzoxepine 核心。与之前展示冗长策略的报告相比，我们展示了迄今为止最短的 radulanin A 合成，其主要特征是 2,2-二甲基色烯前体的光化学扩环反应。鉴于对这种天然产品的除草特性的生物学研究，这项工作适用于大规模制备的连续流动装置。