3,5-bis(benzo[d][1,3]dioxol-5-yl)cyclohex-2-enone | 1312794-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3,5-bis(benzo[d][1,3]dioxol-5-yl)cyclohex-2-enone
• 英文别名: 3,5-Bis(1,3-benzodioxol-5-yl)cyclohex-2-en-1-one；3,5-bis(1,3-benzodioxol-5-yl)cyclohex-2-en-1-one
• CAS: 1312794-17-4
• 化学式: C₂₀H₁₆O₅
• 分子量: 336.344
• InChiKey: FHZZUQPERKHEOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-bis(benzo[d][1,3]dioxol-5-yl)cyclohex-2-enone 在 copper(l) iodide 、 1,10-菲罗啉 、 盐酸羟胺 、 碘 、 sodium acetate 、 三乙胺 、 三甲氧基磷 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 N-(3,5-di(3,4-methylenedioxyphenyl)-phenyl)dichloroethanamide
  参考文献：
  名称：

  铜催化环己烯酮肟酯合成取代伯芳胺

  摘要：

  开发了一种使用环己烯酮肟酯铜催化合成具有间位取代基的伯芳胺的新方案。机理研究表明该反应通过亚胺自由基中间体的分子间 1,5-H 氢原子转移进行。这种方法具有高效率、易于使用的催化剂系统和广泛的官能团耐受性的特点。

  DOI：

  10.1021/acs.orglett.3c03501
• 作为产物：
  描述：

  5-[3,4-(甲二氧基)苯基]-1,3-环己二酮 在 溴 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 0.17h， 生成 3,5-bis(benzo[d][1,3]dioxol-5-yl)cyclohex-2-enone
  参考文献：
  名称：

  Design, Synthesis, and Diversification of 3,5-Substituted Enone Library

  摘要：

  This paper describes the synthesis of a 300 member library of 3,5-substituted enones. The synthesis starts with 6 different bromoenones that are accessed from the corresponding 1,3 diones. These bromides are then diversified by Suzuki coupling with a variety of aromatic and vinyl boronic acids. Additionally a small series of triazoles was synthesized by a Sonogashira coupling reaction dipolar cycloacklition sequence. The library was analyzed by principal component analysis to examine its diversity.

  DOI：

  10.1021/co200070m

文献信息

• Iodine-Promoted Semmler-Wolff Reactions: Step-Economic Access to<i>meta</i>-Substituted Primary Anilines via Aromatization
  作者：Shi-Ke Wang、Xia You、Da-Yuan Zhao、Neng-Jie Mou、Qun-Li Luo

  DOI：10.1002/chem.201701712

  日期：2017.9.4

  An atom‐ and step‐economic access to an array of unprotected meta‐substituted primary anilines was disclosed using the Semmler–Wolff reaction, promoted by molecular iodine. Therein, noble metal catalysts and inert atmosphere are unnecessary while the forcing reaction conditions and the lengthy synthesis can be avoided. The synthetic utility of this approach is evident in the de novo syntheses of three

  利用分子碘促进的Semmler-Wolff反应，揭示了一系列无保护的间位取代的一级苯胺的原子经济和阶梯经济性。其中，不需要贵金属催化剂和惰性气氛，同时可以避免强制反应条件和冗长的合成。这种方法的合成效用在三个具有良好总收率的生物活性分子的从头合成中很明显。
• Design, Synthesis, and Diversification of 3,5-Substituted Enone Library
  作者：Juhienah Khalaf、Maria E. Estrella-Jimenez、Matthew J. Shashack、Sharangdhar S. Phatak、Shuxing Zhang、Scott R. Gilbertson

  DOI：10.1021/co200070m

  日期：2011.7.11

  This paper describes the synthesis of a 300 member library of 3,5-substituted enones. The synthesis starts with 6 different bromoenones that are accessed from the corresponding 1,3 diones. These bromides are then diversified by Suzuki coupling with a variety of aromatic and vinyl boronic acids. Additionally a small series of triazoles was synthesized by a Sonogashira coupling reaction dipolar cycloacklition sequence. The library was analyzed by principal component analysis to examine its diversity.
• Copper-Catalyzed Synthesis of Substituted Primary Arylamines from Cyclohexenone Oxime Esters
  作者：Yong-Jie Kuang、Yan Yu、Min Zhou、Yu-Cheng Yin、Tian Cai、Qun-Li Luo

  DOI：10.1021/acs.orglett.3c03501

  日期：2023.12.8

  A novel protocol has been developed for the Cu-catalyzed synthesis of primary arylamines with meta-substituents using cyclohexenone oxime esters. Mechanistic insights suggest that the reaction proceeds via an intermolecular 1,5-H hydrogen atom transfer of an imine radical intermediate. This approach features high efficiency, a readily available catalyst system, and broad functional group tolerance

  开发了一种使用环己烯酮肟酯铜催化合成具有间位取代基的伯芳胺的新方案。机理研究表明该反应通过亚胺自由基中间体的分子间 1,5-H 氢原子转移进行。这种方法具有高效率、易于使用的催化剂系统和广泛的官能团耐受性的特点。