3-碘-4-甲基苯甲醛 | 58586-55-3

• 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: 3-碘-4-甲基苯甲醛
• 英文名称: 3-iodo-4-methylbenzaldehyde
• 英文别名: 3-Iod-4-methylbenzaldehyd
• CAS: 58586-55-3
• 化学式: C₈H₇IO
• 分子量: 246.047
• InChiKey: JAKBMXYECHUYEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-碘-4-甲基苯甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 (9S)-9-(3-iodo-4-methylphenyl)-1,1-dioxo-3,4,5,6,7,9-hexahydro-2H-thieno[3,2-b]quinolin-8-one
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of a Novel Series of 2,3,5,6,7,9-Hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-Dioxide K_ATP Channel Openers:  Discovery of (−)-(9S)-9-(3-Bromo-4-fluorophenyl)-2,3,5,6,7,9- hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-Dioxide (A-278637), a Potent K_ATP Opener That Selectively Inhibits Spontaneous Bladder Contractions

  摘要：

  Structure-activity relationships were investigated on a novel series of sulfonyldihydropyridine-containing K-ATP openers. Ring sizes, absolute stereochemistry, and aromatic substitution were evaluated for K-ATP activity in guinea pig bladder cells using a fluorescence-based membrane potential assay and in a pig bladder strip assay. The inhibition of spontaneous bladder contractions in vitro was also examined for a select group of compounds. All compounds studied showed greater potency to inhibit spontaneous bladder contractions relative to their potencies to inhibit contractions elicited by electrical stimulation. In an anesthetized pig model of myogenic bladder overactivity, compound 14 and (-)-cromakalim 1 were found to inhibit spontaneous bladder contractions in vivo at plasma concentrations lower than those that affected hemodynamic parameters. Compound 14 showed approximately 5-fold greater selectivity than I in vivo and supports the concept that bladder-selective K-ATP channel openers may have utility in the treatment of overactive bladder.

  DOI：

  10.1021/jm030356w
• 作为产物：
  描述：

  3-碘-4-甲基苯甲酸 在 草酰氯 、 LiAlH(O-t-Bu) 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-碘-4-甲基苯甲醛
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of a Novel Series of 2,3,5,6,7,9-Hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-Dioxide K_ATP Channel Openers:  Discovery of (−)-(9S)-9-(3-Bromo-4-fluorophenyl)-2,3,5,6,7,9- hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-Dioxide (A-278637), a Potent K_ATP Opener That Selectively Inhibits Spontaneous Bladder Contractions

  摘要：

  Structure-activity relationships were investigated on a novel series of sulfonyldihydropyridine-containing K-ATP openers. Ring sizes, absolute stereochemistry, and aromatic substitution were evaluated for K-ATP activity in guinea pig bladder cells using a fluorescence-based membrane potential assay and in a pig bladder strip assay. The inhibition of spontaneous bladder contractions in vitro was also examined for a select group of compounds. All compounds studied showed greater potency to inhibit spontaneous bladder contractions relative to their potencies to inhibit contractions elicited by electrical stimulation. In an anesthetized pig model of myogenic bladder overactivity, compound 14 and (-)-cromakalim 1 were found to inhibit spontaneous bladder contractions in vivo at plasma concentrations lower than those that affected hemodynamic parameters. Compound 14 showed approximately 5-fold greater selectivity than I in vivo and supports the concept that bladder-selective K-ATP channel openers may have utility in the treatment of overactive bladder.

  DOI：

  10.1021/jm030356w

文献信息

• Oxidative Iodination of Deactivated Arenes in Concentrated Sulfuric Acid with I₂/NaIO₄and KI/NaIO₄Iodinating Systems
  作者：Lech Skulski、Lukasz Kraszkiewicz、Maciej Sosnowski

  DOI：10.1055/s-2006-926374

  日期：——

  from NaIO 4 and either I 2 or KI in concentrated H 2 SO 4 (minimum 95% by weight). In general a small excess of the dark brown iodinating solution was used (1.1/1.5 equivalents, for nitrobenzene two equivalents was required). The iodinations were conducted at 25-30 °C with a reaction time of 1-2 hours using either a 'direct' or an 'inverse' method of aromatic iodination to give mono- or diiodinated pure

  用强亲电 I + 试剂对失活的芳烃进行单碘化或二碘化，这些试剂由 NaIO 4 和 I 2 或 KI 在浓 H 2 SO 4 中制备（至少 95% 重量）。通常使用稍微过量的深棕色碘化溶液（1.1/1.5 当量，对于硝基苯需要两个当量）。碘化在 25-30 °C 下进行，反应时间为 1-2 小时，使用芳香族碘化的“直接”或“反向”方法以 31-91% 的优化产率得到单碘化或二碘化纯产物。
• <i>N</i> -Iodosuccinimide (NIS) in Direct Aromatic Iodination
  作者：Maria Bergström、Ganji Suresh、Veluru Ramesh Naidu、C. Rikard Unelius

  DOI：10.1002/ejoc.201700173

  日期：2017.6.16

  N-Iodosuccinimide (NIS) in pure trifluoroacetic acid (TFA) offers a time-efficient and general method for the iodination of a wide range of mono- and disubstituted benzenes at room temperature, as demonstrated in this paper. The starting materials were generally converted into mono-iodinated products in less than 16 hours at room temperature, without byproducts. A few deactivated substrates needed

  如本文所示，纯三氟乙酸（TFA）中的N-碘琥珀酰亚胺（NIS）提供了一种在室温下碘化范围广泛的单取代和二取代苯的高效方法和通用方法。通常将原料在室温下少于16小时内转化为单碘化产物，而没有副产物。一些失活的底物需要添加硫酸以提高反应速率。另一个例外是甲氧基苯，它们优先由NIS在乙腈中碘化，仅具有催化量的TFA。
• Tricyclic dihydropyrazolone and tricyclic dihydroisoxazolone potassium channel openers
  申请人：——

  公开号：US20020007059A1

  公开（公告）日：2002-01-17

  Compounds of formula I 1 are useful in treating diseases prevented by or ameliorated with potassium channel openers. Also disclosed are potassium channel opening compositions and a method of opening potassium channels in a mammal.

  公式I的化合物在治疗由钾通道开放剂预防或改善的疾病中很有用。还公开了钾通道开放组合物和在哺乳动物中开放钾通道的方法。
• Pyrano, piperidino, and thiopyrano compounds and methods of use
  申请人：Abbott Laboratories

  公开号：US06642222B2

  公开（公告）日：2003-11-04

  The present invention provides novel compounds of formula I which may be useful in hyperpolarizing cell membranes, opening potassium channels, relaxing smooth muscle cells, and inhibiting bladder contractions.

  本发明提供了一种公式I的新化合物，可能在超极化细胞膜、打开钾通道、放松平滑肌细胞和抑制膀胱收缩方面有用。
• INSECTICIDAL ARYL ISOXAZOLINE DERIVATIVES
  申请人：Mihara Jun

  公开号：US20100179194A1

  公开（公告）日：2010-07-15

  The present invention relates to novel aryl isoxazoline derivatives having excellent insecticidal activity as insecticides and represented by the formula: and their use as insecticides and acarizides.

  这项发明涉及具有优异杀虫活性的新型芳基异噁唑啉衍生物作为杀虫剂的代表公式： 以及它们作为杀虫剂和杀螨剂的用途。