(Z)-3-(2-iodophenyl)acrylic acid | 1270892-67-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-3-(2-iodophenyl)acrylic acid
• 英文别名: (Z)-3-(2-iodophenyl)prop-2-enoic acid
• CAS: 1270892-67-5
• 化学式: C₉H₇IO₂
• 分子量: 274.058
• InChiKey: SBCFNNJYIXFMFS-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-碘苯甲醛 在 水 、 苄基三甲基氢氧化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 (Z)-3-(2-iodophenyl)acrylic acid
  参考文献：
  名称：

  Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

  摘要：

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.08.013

文献信息

• Selective Palladium-Catalyzed Domino Heck/Buchwald-Hartwig Arylations of<i>N</i>-Glycosylcinnamamides: An Efficient Route to 4-Aryl-<i>N</i>-glycosylquinolin-2-ones
  作者：Thi Thanh Huyen Luong、Sabrina Touchet、Mouad Alami、Samir Messaoudi

  DOI：10.1002/adsc.201601382

  日期：2017.4.17

  An efficient and selective domino Heck/Buchwald–Hartwig arylations of readily available N‐glycosylcinnamamides with aryl iodides have been established. Using palladium(II) acetate as a catalyst, potassium acetate as the base and tetrabutylamonium bromide as an additive in dioxane, the protocol proved to be general, and a variety of 4‐aryl‐N‐glycosylquinolin‐2‐ones has been prepared in good yields with

  已经建立了有效的，选择性的，易于获得的N-糖基肉桂酰胺与芳基碘化物的多米诺Heck / Buchwald-Hartwig芳基化方法。在二恶烷中使用乙酸钯（II）作为催化剂，乙酸钾作为碱，四丁基溴化铵作为添加剂在二恶烷中被证明是通用的，并且已经制备了多种4-芳基-N-糖基喹啉-2-酮。独有的α或β选择性，产量高。