5-碘-2,4-二甲氧基苯甲醛 | 121177-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-碘-2,4-二甲氧基苯甲醛
• 英文名称: 5-iodo-2,4-dimethoxybenzaldehyde
• 英文别名: 2,4-dimethoxy-5-iodobenzaldehyde
• CAS: 121177-67-1
• 化学式: C₉H₉IO₃
• 分子量: 292.073
• InChiKey: RKDRKAVGBBJYJG-UHFFFAOYSA-N

物化性质

• 熔点：
  172-176°C

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• 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

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  5-碘-2,4-二甲氧基苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 四丁基氟化铵 、 三乙胺 、 palladium dichloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.17h， 生成 5-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde
  参考文献：
  名称：

  Carboxylated, Heteroaryl-Substituted Chalcones as Inhibitors of Vascular Cell Adhesion Molecule-1 Expression for Use in Chronic Inflammatory Diseases

  摘要：

  Starting from a simple chalcone template, structure-activity relationship (SAR) studies led to a series of carboxylated, heteroaryl-substituted chalcone derivatives as novel, potent inhibitors of vascular cell adhesion molecule-1 (VCAM-1) expression. Correlations between lipophilicity determined by calculated logP values and inhibitory efficacy were observed among structurally similar compounds of the series. Various substituents were found to be tolerated at several positions of the chalcone backbone as long as the compounds fell into the right range of lipophilicity. The chalcone alpha,beta-unsaturated ketone moiety seemed to be the pharmacophore required for inhibition of VCAM-1 expression. Compound 19 showed significant antiinflammatory effects in a mouse model of allergic inflammation, indicating that this series of compounds might have therapeutic value for human asthma and other inflammatory disorders.

  DOI：

  10.1021/jm0614230
• 作为产物：
  描述：

  5-溴-2,4-二甲氧基苯甲醛 在 palladium diacetate 、 对甲苯磺酸 水 、 一氯化碘 、 sodium carbonate 作用下， 以 甲醇 、 丙酮 、 苯 为溶剂， 反应 15.0h， 生成 5-碘-2,4-二甲氧基苯甲醛
  参考文献：
  名称：

  Carboxylated, Heteroaryl-Substituted Chalcones as Inhibitors of Vascular Cell Adhesion Molecule-1 Expression for Use in Chronic Inflammatory Diseases

  摘要：

  Starting from a simple chalcone template, structure-activity relationship (SAR) studies led to a series of carboxylated, heteroaryl-substituted chalcone derivatives as novel, potent inhibitors of vascular cell adhesion molecule-1 (VCAM-1) expression. Correlations between lipophilicity determined by calculated logP values and inhibitory efficacy were observed among structurally similar compounds of the series. Various substituents were found to be tolerated at several positions of the chalcone backbone as long as the compounds fell into the right range of lipophilicity. The chalcone alpha,beta-unsaturated ketone moiety seemed to be the pharmacophore required for inhibition of VCAM-1 expression. Compound 19 showed significant antiinflammatory effects in a mouse model of allergic inflammation, indicating that this series of compounds might have therapeutic value for human asthma and other inflammatory disorders.

  DOI：

  10.1021/jm0614230

文献信息

• Highly Regioselective Iodination of Arenes via Iron(III)-Catalyzed Activation of <i>N</i>-Iodosuccinimide
  作者：Daugirdas T. Racys、Catherine E. Warrilow、Sally L. Pimlott、Andrew Sutherland

  DOI：10.1021/acs.orglett.5b02345

  日期：2015.10.2

  An iron(III)-catalyzed method for the rapid and highly regioselective iodination of arenes has been developed. Use of the powerful Lewis acid, iron(III) triflimide, generated in situ from iron(III) chloride and a readily available triflimide-based ionic liquid allowed activation of N-iodosuccinimide (NIS) and efficient iodination under mild conditions of a wide range of substrates including biologically

  已经开发了铁（III）催化的用于芳烃的快速和高度区域选择性碘化的方法。使用由氯化铁（III）原位生成的强力路易斯酸，三氟化铁（III）和易于获得的基于三氟化物的离子液体，可以在宽范围的温和条件下活化N-碘代琥珀酰亚胺（NIS）和有效的碘化作用底物，包括生物活性化合物和分子显像剂。
• Silver(I)-Catalyzed Iodination of Arenes: Tuning the Lewis Acidity of <i>N</i>-Iodosuccinimide Activation
  作者：Daugirdas T. Racys、Salaheddin A. I. Sharif、Sally L. Pimlott、Andrew Sutherland

  DOI：10.1021/acs.joc.5b02761

  日期：2016.2.5

  A mild and rapid method for the iodination of arenes that utilizes silver(I) triflimide as a catalyst for activation of N-iodosuccinimide has been developed. The transformation was found to be general for a wide range of anisole, aniline, acetanilide, and phenol derivatives and allowed the late-stage iodination of biologically active compounds such as PIMBA, a SPECT imaging agent of breast cancer,

  已经开发了一种温和且快速的碘化碘的方法，该方法利用三氟甲磺酸银（I）作为活化N-碘代琥珀酰亚胺的催化剂。发现该转化对于广泛的苯甲醚，苯胺，对乙酰苯胺和苯酚衍生物是通用的，并且可以对生物活性化合物（如PIMBA，乳腺癌的SPECT成像剂和（-）-IBZM）进行后期碘化，一种多巴胺D 2受体拮抗剂。还使用一锅法将芳烃的放射性碘化方法进行了修改，该方法涉及原位生成[ 125 I] -N-碘代琥珀酰亚胺，然后进行银（I）催化的碘化。
• Generation of Dimethyl Sulfoxide Coordinated Thermally Stable Halogen Cation Pools for C−H Halogenation
  作者：Pallaba Ganjan Dalai、Kuntal Palit、Niranjan Panda

  DOI：10.1002/adsc.202101291

  日期：2022.3

  A method to generate halogen cation pools from the reaction of 1,2-dihaloethanes (hal=Br, I) and dimethyl sulfoxide (DMSO) for C−H halogenation of arenes and heteroarenes was reported. The initial reaction of DMSO and 1,2-dihaloethane generates the sulfur ylide, which undergoes pyrolytic elimination of ethylene by affording halonium ions. These ions were accumulated and stabilized by DMSO through coordination

  报道了一种通过 1,2-二卤代乙烷 (hal=Br, I) 和二甲基亚砜 (DMSO) 的反应生成卤素阳离子池的方法，用于芳烃和杂芳烃的 C-H 卤化。DMSO 和 1,2-二卤代乙烷的初始反应生成硫叶立德，其通过提供卤离子来热解消除乙烯。DMSO 通过配位形成卤化反应的卤离子池，从而积累和稳定这些离子。该方案在室温下对芳烃的亲电单卤化具有选择性；但是，通过提高反应温度会形成多卤代产物。杂芳烃和一些常用药物的后期卤化表明该协议在药物化学中的合成效用。与经典方法不同，
• Phenalenannulations: Three‐Point Double Annulation Reactions that Convert Benzenes into Pyrenes
  作者：Rahul Kisan Kawade、Chaowei Hu、Nikolas R. Dos Santos、Noelle Watson、Xinsong Lin、Kenneth Hanson、Igor V. Alabugin

  DOI：10.1002/anie.202006087

  日期：2020.8.17

  3‐Point annulations, or phenalenannulations, transform a benzene ring directly into a substituted pyrene by “wrapping” two new cycles around the perimeter of the central ring at three consecutive carbon atoms. This efficient, modular, and general method for π‐extension opens access to non‐symmetric pyrenes and their expanded analogues. Potentially, this approach can convert any aromatic ring bearing

  3点环空（或对苯二烯环化）通过在三个连续的碳原子上围绕中心环的周边“包裹”两个新循环，将苯环直接转化为取代的pyr。这种有效的，模块化的，通用的π扩展方法使人们可以访问非对称pyr及其扩展的类似物。潜在地，这种方法可以将带有-CH 2 Br或-CHO基团的任何芳环转化为a部分。根据后处理的选择，该过程可以直接用于锡或碘取代的产物的形成，为进一步的各种交叉偶联反应提供了补充选择。双向bis-double环空添加了两个新的多芳族延伸基团，中心核心处总共有六个新的芳族环。
• Comparison of Iodination of Methoxylated Benzaldehydes and Related Compounds using Iodine/Silver Nitrate and Iodine/Periodic Acid
  作者：Bruce A. Hathaway、Kristen L. White、Mark E. McGill

  DOI：10.1080/00397910701569080

  日期：2007.10.1

  Abstract Iodination of the three methoxybenzaldehydes, four dimethoxybenzaldehydes, vanillin, and piperonal by two methods were compared. Iodine and periodic acid gave better yields for iodination for the methoxybenzaldehydes, whereas iodine and silver nitrate generally gave better yields for the rest of the compounds.

  摘要 比较了两种方法对三种甲氧基苯甲醛、四种二甲氧基苯甲醛、香兰素和胡椒醛的碘化作用。碘和高碘酸对甲氧基苯甲醛的碘化产率更高，而碘和硝酸银对其余化合物的碘化产率通常更高。