3,5-Diiodo-2-methoxybenzaldehyde | 32024-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-Diiodo-2-methoxybenzaldehyde
• CAS: 32024-13-8
• 化学式: C₈H₆I₂O₂
• mdl: MFCD03031570
• 分子量: 387.943
• InChiKey: YXYUVJVFYYTBMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 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-Diiodo-2-methoxybenzaldehyde 、 丙烯酸甲酯（MA） 在 palladium dichloride 四丁基溴化铵 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 10.0h， 以83%的产率得到(2E,2E')-dimethyl 3,3'-(5-formyl-4-methoxy-1,3-phenylene)diacrylate
  参考文献：
  名称：

  Catalysis and Regioselectivity of the Aqueous Heck Reaction by Pd(0) Nanoparticles under Ultrasonic Irradiation

  摘要：

  An aqueous Heck reaction carried out under ultrasonic irradiation at the ambient temperature (25 degrees C) has been shown in this study to afford high yields of corresponding products. It was found that as a catalyst for the reaction palladium forms nanoparticles in-situ, characterized by transmission electron microscopy (TEM) and X-ray powder diffraction (XRD) analyses, and can be recycled. Furthermore, the Heck reaction under such mild and environmentally friendly conditions offers excellent regioselectivity of para-over ortho-substitution in phenyl iodides especially with electron-donating groups.

  DOI：

  10.1021/jo060372b
• 作为产物：
  描述：

  邻甲氧基苯甲醛 在 碘 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 1.0h， 生成 3,5-Diiodo-2-methoxybenzaldehyde
  参考文献：
  名称：

  水杨醛中质子转移互变异构体三重态的研究

  摘要：

  通过内部重原子效应和灵敏的近红外检测系统，研究了水杨醛中质子转移互变异构体低位三重态的光谱学和动力学。3,5- diiodosalicylaldehyde弱质子转移酮互变异构体磷光用在710纳米处的最大分辨（，Φ OBS ~5.23×10 -4）在77K的甲基环己烷玻璃。结果与时间分辨热透镜实验相结合，进一步推定三重态态的总产率和辐射衰减率分别为0.20（298 K）和。因此，详细讨论了质子传递周期中三重态的能量学和动力学。

  DOI：

  10.1016/s0009-2614(03)00165-9

文献信息

• Wilkinson et al., Biochemical Journal, 1951, vol. 49, p. 714,715
  作者：Wilkinson et al.

  DOI：——

  日期：——
• Iodination of Methylated Anisoles: Unusual Aryl Methyl Replacements and Oxidations
  作者：Charles A. Panetta、Zheng Fang、Daniell L. Mattern

  DOI：10.1021/jo00129a041

  日期：1995.12

  The treatment of methylated anisoles with iodine, periodic acid, sulfuric acid, and aqueous acetic acid has resulted in iododemethylations and/or aryl methyl oxidations in addition to the expected mono- and diiodinations of the aromatic ring. Four dimethylanisoles and o-methylanisole were treated under identical conditions. Iododemethylations were observed in three of the four dimethylanisoles and aryl methyl oxidations to benzaldehydes occurred with o-methylanisole and two of the dimethylanisoles. No precedence could be found for either of these reactions under the experimental conditions employed. Several possible mechanisms are discussed for these transformations. Some experimental evidence suggests that methyl oxidation to a benzaldehyde could be a prerequisite for an iododemethylation via an iodonium ion-assisted reverse Gatterman-Koch reaction; single-electron-transfer or classical electrophilic mechanisms are also consistent with the iododemethylations.
• Catalysis and Regioselectivity of the Aqueous Heck Reaction by Pd(0) Nanoparticles under Ultrasonic Irradiation
  作者：Zuhui Zhang、Zhenggen Zha、Changsheng Gan、Chongfeng Pan、Yuqing Zhou、Zhiyong Wang、Ming-Ming Zhou

  DOI：10.1021/jo060372b

  日期：2006.5.1

  An aqueous Heck reaction carried out under ultrasonic irradiation at the ambient temperature (25 degrees C) has been shown in this study to afford high yields of corresponding products. It was found that as a catalyst for the reaction palladium forms nanoparticles in-situ, characterized by transmission electron microscopy (TEM) and X-ray powder diffraction (XRD) analyses, and can be recycled. Furthermore, the Heck reaction under such mild and environmentally friendly conditions offers excellent regioselectivity of para-over ortho-substitution in phenyl iodides especially with electron-donating groups.
• Studies of the triplet state of the proton-transfer tautomer in salicylaldehydes
  作者：Pi-Tai Chou、Chau-Shuen Chiou、Wei-Shan Yu、Guo-Ray Wu、Tai-Huei Wei

  DOI：10.1016/s0009-2614(03)00165-9

  日期：2003.3

  The spectroscopy and dynamics of the low-lying triplet state of the proton-transfer tautomer in salicylaldehydes have been studied via internal heavy-atom effects coupled with a sensitive near-IR detecting system. For 3,5-diiodosalicylaldehyde a weak proton-transfer keto-tautomer phosphorescence was resolved with a maximum at 710 nm (, Φobs∼5.23×10−4) in a 77 K methylcyclohexane glass. The results

  通过内部重原子效应和灵敏的近红外检测系统，研究了水杨醛中质子转移互变异构体低位三重态的光谱学和动力学。3,5- diiodosalicylaldehyde弱质子转移酮互变异构体磷光用在710纳米处的最大分辨（，Φ OBS ~5.23×10 -4）在77K的甲基环己烷玻璃。结果与时间分辨热透镜实验相结合，进一步推定三重态态的总产率和辐射衰减率分别为0.20（298 K）和。因此，详细讨论了质子传递周期中三重态的能量学和动力学。