(Z)-ethyl 3-(4-iodophenyl)acrylate | 1270893-49-6

• 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)-ethyl 3-(4-iodophenyl)acrylate
• 英文别名: ethyl (Z)-3-(4-iodophenyl)acrylate；ethyl (Z)-3-(4-iodophenyl)prop-2-enoate
• CAS: 1270893-49-6
• 化学式: C₁₁H₁₁IO₂
• 分子量: 302.112
• InChiKey: PJZIVTJXRUYXQX-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (Z)-ethyl 3-(4-iodophenyl)acrylate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以92%的产率得到(Z)-3-(4-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
• 作为产物：
  描述：

  4-碘苯甲醛 、 ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate 在 苄基三甲基氢氧化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以98%的产率得到(Z)-ethyl 3-(4-iodophenyl)acrylate
  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

• Gold(<scp>i</scp>)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes
  作者：Manjur O. Akram、Popat S. Shinde、Chetan C. Chintawar、Nitin T. Patil

  DOI：10.1039/c8ob00630j

  日期：——

  Gold(I)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium

  描述了金（I）催化的芳基重氮盐与有机锡烷的交叉偶联反应。这种氧化还原中性策略为各种联芳基，乙烯基芳烃和芳基乙炔提供了一种有效的方法。用NMR和ESI-MS监测反应为原位形成Ph 3 PAu I R（R =芳基，乙烯基和炔基）物种提供了有力证据，这对于激活芳基重氮盐至关重要。
• Silver-Catalyzed Cross-Olefination of Donor and Acceptor Diazo Compounds: Use of<i>N</i>-Nosylhydrazones as Diazo Surrogate
  作者：Zhaohong Liu、Binbin Liu、Xue-Feng Zhao、Yan-Bo Wu、Xihe Bi

  DOI：10.1002/ejoc.201601610

  日期：2017.1.26

  The cross-olefination reaction of donor and acceptor diazo compounds is reported. The use of N-nosylhydrazones as the diazo surrogates and the dependence on silver catalysis are crucial for the reaction development. A variety of (hetero)aryl N-nosylhydrazones and α-diazo esters, amides, and phosphonates were compatible, affording functionalized alkenes in good-to-high yields with moderate Z/E selectivity

  报道了供体和受体重氮化合物的交叉烯烃化反应。使用 N-nosylhydrazones 作为重氮替代物和对银催化的依赖对于反应发展至关重要。各种（杂）芳基 N-nosylhydrazones 和 α-重氮酯、酰胺和膦酸酯是相容的，以良好到高的产率提供功能化烯烃，Z/E 选择性适中。实验和 DFT 计算结果表明交叉选择性是由于银催化剂对供体重氮化合物的选择性活化。
• Compounds having selective cytochrome P450RAI-1 or selective cytochrome P450RAI-2 inhibitory activity and methods of obtaining the same
  申请人：Vasudevan Jayasree

  公开号：US20080004455A1

  公开（公告）日：2008-01-03

  Compounds of formulas 1 through 17 provided in the specification specifically or selectively inhibit either the cytochrome P450RAI-1 enzyme or the cytochrome P450RAI-2 enzyme.

  公式1到17所提供的化合物，可以特异性地抑制细胞色素P450RAI-1酶或细胞色素P450RAI-2酶。
• US7226951B2
  申请人：——

  公开号：US7226951B2

  公开（公告）日：2007-06-05
• US7638648B2
  申请人：——

  公开号：US7638648B2

  公开（公告）日：2009-12-29