1-(3,4-ethylenedioxyphenyl)-2-iodoethanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 1-(3,4-ethylenedioxyphenyl)-2-iodoethanone
• 英文别名: 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-iodoethanone；Zfbxvtntdrbimw-uhfffaoysa-；1-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-iodoethanone
• 化学式: C₁₀H₉IO₃
• 分子量: 304.084
• InChiKey: ZFBXVTNTDRBIMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,4-ethylenedioxyphenyl)-2-iodoethanone 在 碘 、 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 2,3-dihydro-1,4-benzodioxin-6-yl(oxo)acetaldehyde
  参考文献：
  名称：

  Design and Synthesis of 2-Acylbenzothiazoles via In Situ Cross-Trapping Strategy from Benzothiazoles with Aryl Ketones

  摘要：

  An I-2/KOH synergistically promoted direct ring-opening aroylation of benzothiazoles with aryl ketones has been discovered. Aryl ketones were seen to act as carbonyl sources to construct 2-acylbenzothiazoles. This reaction could provide an example for the convergent integration of self-labor domino sequences based on an in situ cross-trapping strategy.

  DOI：

  10.1021/jo302754c
• 作为产物：
  描述：

  6-乙酰基-1,4-苯并二氧杂环 在 碘 、 copper(II) oxide 作用下， 以 甲醇 为溶剂， 生成 1-(3,4-ethylenedioxyphenyl)-2-iodoethanone
  参考文献：
  名称：

  通过整合来自酮和1,2-二胺的碘化/氧化/环化序列，对喹喔啉进行逻辑设计和合成

  摘要：

  从简单的酮和1,2-二胺开发了一种新颖的喹喔啉合成方案。此过程通过连续碘化经历了一个逻辑方式双-取代的喹喔啉/ kornblum氧化反应/环化在我的存在2 /的CuO / DMSO中，并通过以单取代的喹喔啉碘化/环化/芳构化中的我的存在2 /的CuO / K 3 PO 4 ·3H 2 O.

  DOI：

  10.1016/j.tet.2012.09.056

文献信息

• Logic design and synthesis of quinoxalines via the integration of iodination/oxidation/cyclization sequences from ketones and 1,2-diamines
  作者：Mi Lian、Qi Li、Yanping Zhu、Guodong Yin、Anxin Wu

  DOI：10.1016/j.tet.2012.09.056

  日期：2012.11

  A novel protocol for the synthesis of quinoxalines has been developed from simple ketones and 1,2-diamines. This process underwent a logic approach to bis-substituted quinoxalines via a consecutive iodination/Kornblum oxidation/cyclization in the presence of I2/CuO/DMSO and to mono-substituted quinoxalines via an iodination/cyclization/aromatization in the presence of I2/CuO/K3PO4·3H2O.

  从简单的酮和1,2-二胺开发了一种新颖的喹喔啉合成方案。此过程通过连续碘化经历了一个逻辑方式双-取代的喹喔啉/ kornblum氧化反应/环化在我的存在2 /的CuO / DMSO中，并通过以单取代的喹喔啉碘化/环化/芳构化中的我的存在2 /的CuO / K 3 PO 4 ·3H 2 O.
• Target-oriented synthesis: miscellaneous synthetic routes to access 1,4-enediones through the coupling of 1,3-dicarbonyl compounds with multiform substrates
  作者：Yan-ping Zhu、Qun Cai、Qing-he Gao、Feng-cheng Jia、Mei-cai Liu、Meng Gao、An-xin Wu

  DOI：10.1016/j.tet.2013.05.106

  日期：2013.8

  Target-oriented synthetic protocol was presented for the synthesis of 1,4-enediones. The approach can efficiently construct 1,4-enediones through different reaction pathways from multiform substrates alpha-halo aromatic ketones, 2-hydroxy-aromatic ketones and methyl carbinols. In this reaction, CuI was found to be the most efficient catalyst. Multiform substrates were also found to perform well to afford the products in a one-pot fashion. (C) 2013 Elsevier Ltd. All rights reserved.
• Aerobic oxidative α-iodination of carbonyl compounds using molecular iodine activated by a nitrate-based catalytic system
  作者：Rok Prebil、Stojan Stavber

  DOI：10.1016/j.tetlet.2014.08.055

  日期：2014.10

  The novel reaction system comprising air/NH4NO3(cat.)/I-2/H2SO4(cat.) is introduced as a simple, safe, cheap, efficient, and regioselective mediator for direct aerobic oxidative a-iodination of aryl, heteroaryl, alkyl, and cycloallcyl methyl ketones. The reaction system enabled the moderate to quantitative regioselective iodination of a large range of different methyl ketone derivatives including those bearing oxidizable heteroatom (S, N) substituents. Several activated aromatic compounds were also efficiently and selectively iodinated. The practical applicability of the presented reaction system was shown on 20 mmol scale under ambient pressure and 100% conversion of substrate was achieved. (C) 2014 Elsevier Ltd. All rights reserved.
• Jereb, Marjan; Stavber, Stojan; Zupan, Marko, Synthesis, 2003, # 6, p. 853 - 858
  作者：Jereb, Marjan、Stavber, Stojan、Zupan, Marko

  DOI：——

  日期：——
• Design and Synthesis of 2-Acylbenzothiazoles via In Situ Cross-Trapping Strategy from Benzothiazoles with Aryl Ketones
  作者：Qinghe Gao、Xia Wu、Fengcheng Jia、Meicai Liu、Yanping Zhu、Qun Cai、Anxin Wu

  DOI：10.1021/jo302754c

  日期：2013.3.15

  An I-2/KOH synergistically promoted direct ring-opening aroylation of benzothiazoles with aryl ketones has been discovered. Aryl ketones were seen to act as carbonyl sources to construct 2-acylbenzothiazoles. This reaction could provide an example for the convergent integration of self-labor domino sequences based on an in situ cross-trapping strategy.

表征谱图