7-羟基-2,2-二甲基苯并吡喃 | 19012-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 7-羟基-2,2-二甲基苯并吡喃
• 英文名称: 7-hydroxy-2,2-dimethylchromene
• 英文别名: 2,2-dimethyl-7-hydroxy-2H-1-benzopyran；2,2-dimethylchromen-7-ol
• CAS: 19012-97-6
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: GFXPDSJDSLEZTB-UHFFFAOYSA-N

物化性质

• 沸点：
  94-96 °C(Press: 0.5 Torr)
• 密度：
  1.119±0.06 g/cm3(Predicted)
• 保留指数：
  2266

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  7-羟基-2,2-二甲基苯并吡喃 在 palladium on activated charcoal 氢气 作用下， 以 吡啶 、 正己烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 1-(7-hydroxy-2,2-dimethyl-chroman-8-yl)-ethanone
  参考文献：
  名称：

  7-乙酰氧基苯并吡喃衍生物的光化学。紫杉萜烯和恩斯卡林的合成

  摘要：

  7-乙酰氧基苯并吡喃衍生物1a-5a的光解已经进行。发现Chromene 1a进行了广泛的光聚合。Chromanone 2a经历了效率低下的Photo-Fries重排反应，生成6-和8-乙酰基衍生物2b和2c。Diacetoxychromene图3a，得到不饱和酮8作为主要产物，除了它的脱乙酰化类似物9和二氢吡喃酮11。二乙酰氧基铬烷4a提供了四种C-乙酰基产物的混合物：1b，1c，2b和2c，以及Chromene 1a和苯并二氢吡喃酮2a。最后，苯并二氢吡喃5a的辐射产生了两种可能的光炸产物5b（43％）和5c（52％）的混合物。讨论了以上结果的机理意义，特别强调了与吡喃环，烯醇酯和苄基酯部分相比，苯酯的光反应性。这些转化的合成应用通过制备紫杉烯酮1b和encecalin 1e进行了说明。

  DOI：

  10.1016/s0040-4020(01)89221-8
• 作为产物：
  描述：

  3,3-二甲基丙烯酸 在 sodium tetrahydroborate 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 7-羟基-2,2-二甲基苯并吡喃
  参考文献：
  名称：

  Enantioselective reduction of 4-chromanone and its derivatives by selected filamentous fungi

  摘要：

  Biotransformation of 4-chromanone and its derivatives in the cultures of three biocatalysts: Didymosphaeria igniaria, Colyneum betulinum and Chaetomium sp. is presented. The biocatalysts were chosen due to their capability of enantiospecific reduction of low-molecular-weight ketones (acetophenone and its derivatives and alpha- and beta-tetralone). The substrates were reduced to the respective S-alcohols with high enantiomeric excesses, according to the Prelog's rule. In the culture of Chaetomium sp. after longer biotransformation time an inversion of configuration of the formed alcohols was also observed. The highest yield of transformation was observed for 6-methyl-4-chromanone. In all the tested cultures, the higher was the molecular weight of a chromanone, the lower conversion percent was observed. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.09.004

文献信息

• Studies of chromenes. Part 9. Syntheses of chromenequinones
  作者：Philip E. Brown、Robert A. Lewis、Mark A. Waring

  DOI：10.1039/p19900002979

  日期：——

  Syntheses of 2,2-dimethylchromene-5,8-quinone, 2,2-dimethylchromene-6,7-quinone, and 6,7-dimethoxy-2,2-dimethylchromene-5,8-quinone are described. Being easily bioreducible to electron-rich chromenes these compounds, and their oxirane derivatives, are of interest as possible anti-tumour alkylating agents.

  描述了2，2-二甲基色烯-5，8-醌，2，2-二甲基色烯-6，7-醌和6，7-二甲氧基-2，2-二甲基色烯-5，8-醌的合成。这些化合物及其环氧乙烷衍生物易于被富电子的二烯生物还原，因此作为可能的抗肿瘤烷基化剂受到关注。
• Natural Product-like Combinatorial Libraries Based on Privileged Structures. 1. General Principles and Solid-Phase Synthesis of Benzopyrans
  作者：K. C. Nicolaou、J. A. Pfefferkorn、A. J. Roecker、G.-Q. Cao、S. Barluenga、H. J. Mitchell

  DOI：10.1021/ja002033k

  日期：2000.10.1

  report a novel strategy for the design and construction of natural and natural product-like libraries based on the principle of privileged structures, a term originally introduced to describe structural motifs capable of interacting with a variety of unrelated molecular targets. The identification of such privileged structures in natural products is discussed, and subsequently the 2,2-dimethylbenzopyran

  在此，我们报告了一种基于特权结构原理设计和构建天然和天然产物类库的新策略，该术语最初用于描述能够与各种不相关的分子靶标相互作用的结构基序。讨论了天然产物中此类特权结构的鉴定，随后选择 2,2-二甲基苯并吡喃部分作为通过该策略构建类天然产物库的初始模板。最初，采用独特的环加载策略开发了苯并吡喃基序的新型固相合成，该策略依赖于使用新的聚苯乙烯基溴化硒树脂。一旦确定了这些苯并吡喃的加载、加工和裂解，
• Concise Synthesis of Chromene/Chromane-Type Aryne Precursors and Their Applications
  作者：Yuan-Ze Xu、Jia-Wei Tian、Feng Sha、Qiong Li、Xin-Yan Wu

  DOI：10.1021/acs.joc.1c00493

  日期：2021.5.7

  The gram-scale synthesis of 5,6-, 6,7-, and 7,8-chromene/chromane-type aryne precursors and their applications in regioselective transformation to other functional derivatives is reported. Chromene/chromane-type arynes are generated under mild conditions, which can further undergo [2 + 2], [3 + 2], and [4 + 2] cycloaddition reactions, nucleophilic addition reactions, and σ-insertion reactions to produce

  报道了5,6-，6,7-和7,8-亚甲基/苯并二氢吡喃型芳烃前体的克级合成及其在向其他功能衍生物的区域选择性转化中的应用。Chromene / chromane型芳烃是在温和条件下产生的，可以进一步进行[2 + 2]，[3 + 2]和[4 + 2]环加成反应，亲核加成反应和σ插入反应，从而产生结构新颖的取代的色烯和苯并二氢吡喃。在三键邻位的含氧引导基团促进了反应的优异区域选择性，该基团可以被除去或切换成其他官能团，包括烯基，芳基，杂芳基和芳基氨基。
• Regioselective Prenylation of Phenols by Palladium Catalyst: Syntheses of Prenylphenols and Chromans
  作者：Masao Tsukayama、Makoto Kikuchi、Yasuhiko Kawamura

  DOI：10.3987/com-94-6744

  日期：——

  The palladium-catalyzed coupling reaction of iodophenols (1) with 2-methyl-3-butyn-2-ol gave alkynylphenols (2). Catalytic hydrogenation of 2 over Raney nickel and the subsequent dehydration of the resultant alkylphenols (3) gave regioselectively the desired prenylphenols (4). Dehydration of alkylphenols (3f-h) gave chromans (7).
• Enantioselective syntheses of decursinol angelate and decursin
  作者：Jongdoo Lim、Ik-Hwan Kim、Hyeon Ho Kim、Kyung-Seop Ahn、Hogyu Han

  DOI：10.1016/s0040-4039(01)00642-6

  日期：2001.6

  The practical enantioselective syntheses of decursinol angelate and decursin were achieved in eight steps from resorcinol. The stereochemistry was addressed using the catalytic asymmetric epoxidation of 7-acetoxy-2,2-dimethylchromene by chiral (salen)Mn complexes as the key step. (C) 2001 Elsevier Science Ltd. All rights reserved.