3,5-dimethyl-2-prop-2-enyloxybenzaldehyde | 1222435-66-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-dimethyl-2-prop-2-enyloxybenzaldehyde
• 英文别名: 3,5-Dimethyl-2-prop-2-enoxybenzaldehyde
• CAS: 1222435-66-6
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: YSJPIKYNGXTVJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-dimethyl-2-prop-2-enyloxybenzaldehyde 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 potassium carbonate 、 甲基磺酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 2-[(3,5-dimethyl-2-prop-2-enyloxyphenyl)methoxy]-3,5-dimethylbenzaldehyde
  参考文献：
  名称：

  Cationic Ring-Opening Polymerization of 1,3-Benzoxazines: Mechanistic Study Using Model Compounds

  摘要：

  The benzoxazine monomer is used to simplify the study of the benzoxazine initiation mechanism. The HPLC retention time and the H-1 NMR spectra of crude products from the benzoxazine reaction are compared with the results from a vast number of pure model compounds, which are synthesized based on the hypothesized mechanisms. Products involved in the process are identified, with species having benzoxazine structures, Mannich base and other components (acetal, nonacetal phenoxy structures, and methylene bridge structure). Initiation mechanisms of benzoxazine, the oxygen protonation and the nitrogen protonation, are proposed.

  DOI：

  10.1021/ma901743h
• 作为产物：
  描述：

  2,4-二甲基苯酚 在 甲基溴化镁 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 生成 3,5-dimethyl-2-prop-2-enyloxybenzaldehyde
  参考文献：
  名称：

  Cationic Ring-Opening Polymerization of 1,3-Benzoxazines: Mechanistic Study Using Model Compounds

  摘要：

  The benzoxazine monomer is used to simplify the study of the benzoxazine initiation mechanism. The HPLC retention time and the H-1 NMR spectra of crude products from the benzoxazine reaction are compared with the results from a vast number of pure model compounds, which are synthesized based on the hypothesized mechanisms. Products involved in the process are identified, with species having benzoxazine structures, Mannich base and other components (acetal, nonacetal phenoxy structures, and methylene bridge structure). Initiation mechanisms of benzoxazine, the oxygen protonation and the nitrogen protonation, are proposed.

  DOI：

  10.1021/ma901743h

文献信息

• Organophotoredox‐Catalyzed Cascade Radical Annulation of 2‐(Allyloxy)arylaldehydes with <i>N</i> ‐(acyloxy)phthalimides: Towards Alkylated Chroman‐4‐one Derivatives
  作者：Sanju Das、Sushanta Kumar Parida、Tanumoy Mandal、Laxmikanta Sing、Suman De Sarkar、Sandip Murarka

  DOI：10.1002/asia.201901735

  日期：2020.3.2

  approach for the synthesis of highly important 3-alkyl substituted chroman-4-one scaffold is developed using visible light induced radical cascade cyclization strategy. The reaction is initiated through the generation of alkyl radicals from N-(acyloxy)phthalimides under photoredox conditions, which subsequently undergo intermolecular cascade radical cyclization on 2-(allyloxy)arylaldehydes to afford chroman-4-one

  使用可见光诱导的自由基级联环化策略，开发了有机光氧化还原催化的高效且稳健的方法，用于合成高度重要的3-烷基取代的chroman-4-one支架。该反应通过在光氧化还原条件下由N-（酰氧基）邻苯二甲酰亚胺生成烷基而引发，随后在2-（烯丙氧基）芳基醛上进行分子间的级联自由基环化，从而得到苯并吡喃-4-酮骨架。提出的策略在温和的反应条件，操作简便，高官能团耐受性和广泛的底物范围方面具有吸引力。
• 一种2,3-二氢苯并吡喃-4-酮衍生物的制备方 法
  申请人：浙江圣效化学品有限公司

  公开号：CN107586285B

  公开（公告）日：2020-09-01

  本发明提供了一种制备2,3‑二氢苯并吡喃‑4‑酮衍生物的制备方法，包括如下步骤：在氮气气氛、室温下将式(Ⅰ)所示的邻丙烯基氧基苯甲醛衍生物和式(Ⅱ)所示的安息香衍生物溶解在有机溶剂中，加入光敏剂混合均匀后，置于在紫外灯下光照反应后，旋蒸去除溶剂后经硅胶柱层析分离纯化，所得产物即为2,3‑二氢苯并吡喃‑4‑酮衍生物。本发明所述制备方法解决了现有合成方法步骤繁琐、产率低、方法环保性差的问题，在常温常压下即可反应，反应条件温和，无需过渡金属催化，具有操作简单、无污染、安全环保、成本低等优点。其中，R1、R2为氢、卤素或烷基。
• Cationic Ring-Opening Polymerization of 1,3-Benzoxazines: Mechanistic Study Using Model Compounds
  作者：Papinporn Chutayothin、Hatsuo Ishida

  DOI：10.1021/ma901743h

  日期：2010.5.25

  The benzoxazine monomer is used to simplify the study of the benzoxazine initiation mechanism. The HPLC retention time and the H-1 NMR spectra of crude products from the benzoxazine reaction are compared with the results from a vast number of pure model compounds, which are synthesized based on the hypothesized mechanisms. Products involved in the process are identified, with species having benzoxazine structures, Mannich base and other components (acetal, nonacetal phenoxy structures, and methylene bridge structure). Initiation mechanisms of benzoxazine, the oxygen protonation and the nitrogen protonation, are proposed.