(E)-2-ethoxy-4-(2-nitrovinyl)phenol | 90922-85-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-2-ethoxy-4-(2-nitrovinyl)phenol
• 英文别名: 3-ethoxyl-4-methoxy-β-nitrostyrene；2-ethoxy-4-(trans-2-nitro-vinyl)-phenol；2-Aethoxy-4-(trans-2-nitro-vinyl)-phenol；2-Ethoxy-4-[(e)-2-nitroethenyl]phenol
• CAS: 90922-85-3
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: GAJIQLKTZKVZAJ-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-苯基-1H-吲唑-3-醇 、 (E)-2-ethoxy-4-(2-nitrovinyl)phenol 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以71%的产率得到(Z)-5-(3-ethoxy-4-hydroxyphenyl)-6-(hydroxyimino)-5H-indazolo[1,2-a]cinnolin-8(6H)-one
  参考文献：
  名称：

  还原剂-免费收敛羟基亚装饰四环融合噌的通过合成的Rh三催化的环使用Nitroolefins

  摘要：

  开发了一种温和的Rh催化方法，通过还原1-芳基吲唑酮和2-芳基-[4 + 2]环合反应，合成羟基亚氨基官能化的吲唑并[1,2- a ] cinnolines和邻苯并[2,3- a ] cinnolines。 2,3-二氢酞嗪-1,4-二酮与各种硝基烯烃。在无还原剂的条件下，通过连续的C–H活化/烯烃插入/还原反应，合成了目标肟肟修饰的四环稠合肉桂醛。

  DOI：

  10.1021/acs.joc.0c02729
• 作为产物：
  描述：

  乙基香兰素 、 硝基甲烷 在 ammonium acetate 作用下， 反应 24.0h， 生成 (E)-2-ethoxy-4-(2-nitrovinyl)phenol
  参考文献：
  名称：

  The synthesis and biologic evaluation of anti-platelet and cytotoxic β-nitrostyrenes

  摘要：

  Our previous studies demonstrated that two cytotoxic beta-nitrostyrene derivatives, 3,4-methylenedioxy-beta-nitrostyrene (MNS) and 4-O-benzoyl-3-methoxy-beta-nitrostyrene (BMNS) exhibit potent anti-platelet activities. In this study, a series of beta-nitrostyrenes were synthesized and subjected to anti-platelet aggregation assay and cytotoxicity assay. The mono-and di-substitutions on the B ring of BMNS tended to increase the anti-platelet activity and decrease the cytotoxic activity. Of these, compounds 19 and 24 exhibited the most potent inhibitory effects on thrombin-and collagen-induced platelet aggregation (IC(50) <= 0.7 mu M) without significant cytotoxicity on a human cancer cell line (up to 20 mu M). Further studies indicated that compounds 19 and 24 inhibited platelet aggregation via prevention of glycoprotein IIb/IIIa activation. The potent and novel effects of BMNS derivatives make them attractive candidates for the development of new anti-platelet agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.039

文献信息

• THE SYNTHESIS OF ι-NITROSTYRENES¹
  作者：CATHERINE B. GAIRAUD、GERALD R. LAPPIN

  DOI：10.1021/jo01129a001

  日期：1953.1
• Reducing-Agent-Free Convergent Synthesis of Hydroxyimino-Decorated Tetracyclic Fused Cinnolines via Rh^III-Catalyzed Annulation Using Nitroolefins
  作者：Pidiyara Karishma、Chikkagundagal K. Mahesha、Sanjay K. Mandal、Rajeev Sakhuja

  DOI：10.1021/acs.joc.0c02729

  日期：2021.2.5

  A mild Rh-catalyzed method was developed for the synthesis of hydroxyimino functionalized indazolo[1,2-a]cinnolines and phthalazino[2,3-a]cinnolines by reductive [4 + 2] annulation between 1-arylindazolones and 2-aryl-2,3-dihydrophthalazine-1,4-diones with varied nitroolefins. The targeted oxime decorated tetracyclic fused cinnolines were synthesized via sequential C–H activation/olefin insertion/reduction

  开发了一种温和的Rh催化方法，通过还原1-芳基吲唑酮和2-芳基-[4 + 2]环合反应，合成羟基亚氨基官能化的吲唑并[1,2- a ] cinnolines和邻苯并[2,3- a ] cinnolines。 2,3-二氢酞嗪-1,4-二酮与各种硝基烯烃。在无还原剂的条件下，通过连续的C–H活化/烯烃插入/还原反应，合成了目标肟肟修饰的四环稠合肉桂醛。
• The synthesis and biologic evaluation of anti-platelet and cytotoxic β-nitrostyrenes
  作者：Pei-Wen Hsieh、Yu-Ting Chang、Wen Yin Chuang、Hsin-Chu Shih、Shin-Zan Chiang、Chin-Chung Wu

  DOI：10.1016/j.bmc.2010.08.039

  日期：2010.11

  Our previous studies demonstrated that two cytotoxic beta-nitrostyrene derivatives, 3,4-methylenedioxy-beta-nitrostyrene (MNS) and 4-O-benzoyl-3-methoxy-beta-nitrostyrene (BMNS) exhibit potent anti-platelet activities. In this study, a series of beta-nitrostyrenes were synthesized and subjected to anti-platelet aggregation assay and cytotoxicity assay. The mono-and di-substitutions on the B ring of BMNS tended to increase the anti-platelet activity and decrease the cytotoxic activity. Of these, compounds 19 and 24 exhibited the most potent inhibitory effects on thrombin-and collagen-induced platelet aggregation (IC(50) <= 0.7 mu M) without significant cytotoxicity on a human cancer cell line (up to 20 mu M). Further studies indicated that compounds 19 and 24 inhibited platelet aggregation via prevention of glycoprotein IIb/IIIa activation. The potent and novel effects of BMNS derivatives make them attractive candidates for the development of new anti-platelet agents. (C) 2010 Elsevier Ltd. All rights reserved.