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

• 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: 1-(3,4-methylenedioxyphenyl)-2-iodoethanone
• 英文别名: 1-(1,3-Benzodioxol-5-yl)-2-iodoethanone
• 化学式: C₉H₇IO₃
• 分子量: 290.057
• InChiKey: BVPGPOKNKIMCLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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-methylenedioxyphenyl)-2-iodoethanone 在 碘 、 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 3,4-methylenedioxyphenylglyoxal
  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：

  3,4-亚甲二氧苯乙酮 在 碘 、 copper(II) oxide 作用下， 以 乙醇 为溶剂， 生成 1-(3,4-methylenedioxyphenyl)-2-iodoethanone
  参考文献：
  名称：

  I 2 / CuO催化串联环化策略，可从易于获得的芳族酮/α，β-不饱和酮和硫脲一锅法合成取代的2-氨基噻唑

  摘要：

  开发了一种由易得的甲基酮/不饱和甲基酮和硫脲组成的简洁高效的一锅法，用于在I 2 / CuO介质下合成2-氨基噻唑。该方法可以高度立体选择性地获得4-乙烯基-2-氨基噻唑的电子异构体（5a–f）。所有这些目标分子均通过NMR，HRMS和IR光谱进行了表征。此外，通过X射线晶体学分析进一步确定目标化合物3c和5b。

  DOI：

  10.1016/j.tet.2011.10.074

文献信息

• A direct method for the synthesis of indolizine derivatives from easily available aromatic ketones, pyridines, and acrylonitrile derivatives
  作者：Qun Cai、Yan-Ping Zhu、Yang Gao、Jing-Jing Sun、An-Xin Wu

  DOI：10.1139/cjc-2012-0534

  日期：2013.6

  A concise and efficient strategy has been proposed to synthesize indolizine derivatives from easily available aryl or heteroaryl methyl ketones, pyridines, and acrylonitriles. The mechanistic pathway involved the integration of iodination, pyridinium ylide synthesis, and 1,3-dipolar cycloaddition. The protocols were found to be highly efficient in terms of high yields, operational simplicity, mild reaction conditions, and easy workup. This method has provided an important supplement for the synthesis of indolizine derivatives via a novel tandem synthesis.

  已提出一种简洁高效的策略，可从易得的芳基或杂环芳基甲基酮、吡啶和丙烯腈合成吲哚啉衍生物。机理途径涉及碘化、吡啶铵叶立德合成和1,3-二极环加成的整合。该方案在高产率、操作简便、温和反应条件和易于操作等方面表现出高效性。这种方法为通过新颖串联合成合成吲哚啉衍生物提供了重要补充。
• Highly Efficient and Clean Method for Direct α-Iodination of Aromatic Ketones
  作者：Anxin Wu、Yuanjiang Pan、Guodong Yin、Meng Gao、Nengfang She、Shengli Hu

  DOI：10.1055/s-2007-983880

  日期：2007.10

  Under neutral reaction conditions, aromatic ketones were transformed into the corresponding α-iodo ketones in high yields by the combination of copper(II) oxide and iodine. The reaction mechanism showed that copper(II) oxide played multiple roles through random self-sorting.

  在中性反应条件下，芳香酮通过铜(II)氧化物和碘的组合高效转化为相应的α-碘酮。反应机理表明，铜(II)氧化物通过随机自分类发挥多重作用。
• I2/CuO-catalyzed tandem cyclization strategy for one-pot synthesis of substituted 2-aminothiozole from easily available aromatic ketones/α,β-unsaturated ketones and thiourea
  作者：Yan-Ping Zhu、Jing-Jing Yuan、Qin Zhao、Mi Lian、Qing-He Gao、Mei-Cai Liu、Yan Yang、An-Xin Wu

  DOI：10.1016/j.tet.2011.10.074

  日期：2012.1

  A concise and efficient one-pot process from easily available methyl ketones/unsaturated methyl ketones and thiourea was developed for the synthesis of 2-aminothiazoles under the media of I2/CuO. The method can highly stereoselectivity obtain the E-isomers of 4-ethenyl-2-aminothiazoles (5a–f). All these target molecules were characterized by NMR, HRMS and IR spectra. Furthermore, the target compounds

  开发了一种由易得的甲基酮/不饱和甲基酮和硫脲组成的简洁高效的一锅法，用于在I 2 / CuO介质下合成2-氨基噻唑。该方法可以高度立体选择性地获得4-乙烯基-2-氨基噻唑的电子异构体（5a–f）。所有这些目标分子均通过NMR，HRMS和IR光谱进行了表征。此外，通过X射线晶体学分析进一步确定目标化合物3c和5b。
• 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.
• Jereb, Marjan; Stavber, Stojan; Zupan, Marko, Synthesis, 2003, # 6, p. 853 - 858
  作者：Jereb, Marjan、Stavber, Stojan、Zupan, Marko

  DOI：——

  日期：——