(E)-2-methoxy-4-(2-nitroprop-1-enyl)phenol | 74273-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-2-methoxy-4-(2-nitroprop-1-enyl)phenol
• 英文别名: 2-Methoxy-4-(2-nitro-propen-(1)-yl-(1c))-phenol；2-Methoxy-4-(2-nitro-cis-propenyl)-phenol；1-(4-Hydroxy-3-methoxyphenyl)-2-nitropropene；2-methoxy-4-[(E)-2-nitroprop-1-enyl]phenol
• CAS: 74273-16-8
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: FDLWTEUMNRJFCS-FNORWQNLSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  349.8±27.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 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：

  (E)-2-methoxy-4-(2-nitroprop-1-enyl)phenol 在 N-乙基吗啉 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 7.33h， 生成 4-({[2-methoxy-4-(trans-2-nitro-1-propenyl)phenyl]oxy}sulfonyl)benzoic acid N-methylamide
  参考文献：
  名称：

  Sulfonylbenzoyl-nitrostyrenes: Potential bisubstrate type inhibitors of the EGF-receptor tyrosine protein kinase

  摘要：

  The synthesis and biological activities of a series of sulfonylbenzoyl-nitrostyrene derivatives, a novel class of selective bisubstrate type inhibitors of the EGF-receptor tyrosine protein kinase, are described. The most potent derivatives inhibited the EGF-R tyrosine kinase, using angiotensin II as exogenous substrate, with IC50 values of less-than-or-equal-to 1-mu-M. No inhibition of the v-abl tyrosine kinase or the serine/threonine kinases PKC and PK-A was observed. In addition, active derivatives (compounds 5 and 12) effectively blocked the autophosphorylation of the EGF-R in vitro. Starting from the acids 5, 7, and 9, a series of esters, amides, and peptides was synthesized with the aim of increasing cellular penetration. Amides 14-18 showed potent antiproliferative effects using the EGF-dependent Balb/MK mouse epidermal keratinocyte cell line. Additionally, with the amide 14 inhibition of EGF-R autophosphorylation was demonstrated in the A431 cell line. CAMM studies using a computer-generated model for the transition state of the gamma-phosphoryl transfer from ATP to a tyrosine moiety and fitting experiments using the highly potent derivative 7 (IC50 value = 54 nM) support the hypothesis that the sulfonylbenzoyl group mimics a diphosphate moiety in the transition state. These results demonstrate that the rational design of tyrosine kinase inhibitors, using the inhibitory nitrostyrene moiety as a tyrosine mimic together with the sulfonylbenzoyl moiety as a diphosphate mimic, leads to highly potent and selective multisubstrate type inhibitors.

  DOI：

  10.1021/jm00112a003
• 作为产物：
  描述：

  1-acetoxy-2-methoxy-4-(2-nitro-1-nitroso-propyl)-benzene 在 氢氧化钾 作用下， 生成 (E)-2-methoxy-4-(2-nitroprop-1-enyl)phenol
  参考文献：
  名称：

  Bruckner; Kramli, Journal fur praktische Chemie (Leipzig 1954), 1935, vol. <2> 143, p. 287,292

  摘要：

  DOI：

文献信息

• Ethylenediamine: A Highly Effective Catalyst for One-Pot Synthesis of Aryl Nitroalkenes via Henry Reaction and Dehydration
  作者：Jianxin Yang、Jing Dong、Xia Lü、Qiang Zhang、Wei Ding、Xiaoxin Shi

  DOI：10.1002/cjoc.201201094

  日期：2012.12

  Ethylenediamine (H2NCH2CH2NH2) was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane (or nitroethane). When 1%–2% (mol%) of ethylenediamine was used as the catalyst, the one‐pot reaction of aryl aldehydes with nitromethane (or nitroethane) by refluxing for 3–10 h efficiently afforded various arylnitroalkenes 1a–1y in 85%–97% yields.

  发现乙二胺（H 2 NCH 2 CH 2 NH 2）是芳基醛与硝基甲烷（或硝基乙烷）缩合的高效催化剂。当使用1％–2％（mol％）的乙二胺作为催化剂时，芳基醛与硝基甲烷（或硝基乙烷）的单锅反应通过回流3–10 h可有效地得到85％–的各种芳基硝基烯烃1a – 1y。产率为97％。
• Microwave-assisted Henry reaction: Solventless synthesis of conjugated nitroalkenes
  作者：Rajender S. Varma、Rajender Dahiya、Sudhir Kumar

  DOI：10.1016/s0040-4039(97)01093-9

  日期：1997.7

  In a solventless system and under microwave irradiation, nitroalkanes react with arylaldehydes in the presence of a catalytic amount of ammonium acetate to afford, in one step, conjugated nitroalkenes without the isolation of intermediary β-nitro alcohols.

  在无溶剂系统中和在微波辐射下，硝基烷烃与芳醛在催化量的乙酸铵存在下反应，一步一步制得共轭硝基烯烃，而无需分离中间体β-硝基醇。
• Studies on Lignin and Related Compounds. LXVIII. Synthesis and Properties of 1-Ethoxy-1-(4-hydroxy-3-methoxyphenyl)-2-propanone, 3-Ethoxy-1-(4-hydroxy-3-methoxyphenyl)-2-propanone and Their Methyl Ethers
  作者：Marshall Kulka、Harold Hibbert

  DOI：10.1021/ja01246a047

  日期：1943.6
• β-Nitrostyrene derivatives as potential antibacterial agents: A structure–property–activity relationship study
  作者：Nuno Milhazes、Rita Calheiros、M. Paula M. Marques、Jorge Garrido、M. Natália D.S. Cordeiro、Cátia Rodrigues、Sandra Quinteira、Carla Novais、Luísa Peixe、Fernanda Borges

  DOI：10.1016/j.bmc.2006.02.006

  日期：2006.6

  A multidisciplinary project was developed, combining the synthesis of a series of beta-nitrostyrene derivatives and the determination of their physicochemical parameters (redox potentials, partition coefficients), to the evaluation of the corresponding antibacterial activity. A complete conformational analysis was also performed, in order to get relevant structural information. Subsequently, a structure-property-activity (SPAR) approach was applied, through linear regression analysis, aiming at obtaining a putative correlation between the physicochemical parameters of the compounds investigated and their antibacterial activity (both against standard strains and clinical isolates). The beta-nitrostyrene compounds displayed a lower activity towards all the tested bacteria relative to the beta-methyl-beta-nitrostyrene analogues. This was observed particularly for the 3-hydroxy-4-methoxy-beta-methyl-beta-nitrostyrene (IVb) against the Gram-positive bacteria (Staphylococcus aureus, Enterococcus faecalis and Enterococcus faecium). The SPAR results revealed the existence of a clear correlation between the redox potentials and the antibacterial activity of the series of beta-nitrostyrene derivatives under study. (c) 2006 Elsevier Ltd. All rights reserved.
• Kabalka, George W.; Pace, R. David; Wadgaonkar, P.P., Synthetic Communications, 1990, vol. 20, # 16, p. 2453 - 2458
  作者：Kabalka, George W.、Pace, R. David、Wadgaonkar, P.P.

  DOI：——

  日期：——