(E)-1-ethoxy-4-(2-nitrovinyl)benzene | 6946-30-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-1-ethoxy-4-(2-nitrovinyl)benzene
• 英文别名: 1-Ethoxy-4-[(E)-2-nitroethenyl]benzene
• CAS: 6946-30-1
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: LCRQRRBRHHLEHO-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 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：
  55
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  (E)-1-ethoxy-4-(2-nitrovinyl)benzene 在 三乙基硅烷 、 四氯化钛 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 3-(4-Ethoxy-benzyl)-4,5-dihydro-isoxazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  氯化钛（IV）-三乙基硅烷介导的υ-硝基苯乙烯转化为苯基乙酰羟肟基氯

  摘要：

  报道了一种通过与TiCl 4 -Et 3 SiH反应从υ-硝基苯乙烯中分离出迄今未知的苯基乙酰羟肟基氯的新方法。

  DOI：

  10.1016/0040-4039(94)88438-2
• 作为产物：
  描述：

  4-乙氧基苯乙烯 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 dipotassium peroxodisulfate 、 sodium nitrite 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以72%的产率得到(E)-1-ethoxy-4-(2-nitrovinyl)benzene
  参考文献：
  名称：

  K 2 S 2 O 8 -mediated nitration of alkenes with NaNO 2 and 2,2,6,6-tetramethylpiperidine-1-oxyl: stereoselective synthesis of ( E )-nitroalkenes

  摘要：

  A transition-metal-free nitration of alkenes with NaNO2 in the presence of K2S2O8 and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) is developed. The transformation exhibits a broad substrate scope and good functional group tolerance, thus providing a new and expedient protocol for stereoselective synthesis of (E)-nitroalkenes with moderate to good yields. Moreover, the nitration processes of (E)- and (Z)-stilbene are also studied: even though the proportion of substrates is different, the E/Z ratio of the products is basically the same. Based upon experimental observations, a possible reaction mechanism is proposed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.11.064

文献信息

• Synthesis, Antiproliferative and Pro-Apoptotic Effects of Nitrostyrenes and Related Compounds in Burkitt's Lymphoma
  作者：Andrew J. Byrne、Sandra A. Bright、Darren Fayne、James P. McKeown、Thomas McCabe、Brendan Twamley、Clive Williams、Mary J. Meegan

  DOI：10.2174/1573406413666171002123907

  日期：2018.2.6

  identified as a lead target structure for the development of particularly effective compounds targeting Burkitt's lymphoma (BL). OBJECTIVES The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt's lymphoma (BL). METHODS A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions.

  背景技术淋巴细胞癌（淋巴瘤）约占全世界恶性疾病的12％。硝基苯乙烯支架被认为是开发针对Burkitt淋巴瘤（BL）的特别有效的化合物的主要靶标结构。目的目前的研究目的是合成一组硝基苯乙烯化合物并评估其在伯基特氏淋巴瘤（BL）中的活性。方法使用Henry Knoevenagel缩合反应设计和合成一组结构变化的化合物。单晶X射线分析证实了这些新颖结构的六个实例的E构型。还研究了许多与硝基苯乙烯有关的化合物，包括1，3-双（芳基）-2-硝基丙烯与含有硝基乙烯基药效团的杂环支架，例如3-硝基-2-苯基-2H-色烯。使用BL细胞系EBV-MUTU-1和EBV + DG-75（耐化学性）评估化合物的抗增殖活性，以建立初步的结构活性关系。结果成功建立了具有优化的硝基苯乙烯骨架和3-硝基-2-苯基-2Hchromne结构的铅化合物，在MUTU-1细胞中的典型IC50值分别为0.45 µM和0.47 µM，
• Geometrically Selective Denitrative Trifluoromethylthiolation of β-Nitrostyrenes with AgSCF₃ for (<i>E</i>)-Vinyl Trifluoromethyl Thioethers
  作者：Changge Zheng、Shuai Huang、Yang Liu、Chao Jiang、Wei Zhang、Ge Fang、Jianquan Hong

  DOI：10.1021/acs.orglett.0c01714

  日期：2020.6.19

  An efficient copper(II)-promoted denitrative trifluoromethylthiolation under mild reaction conditions has been developed for vinyl trifluoromethyl thioethers to construct Cvinyl–SCF3 bonds with stable AgSCF3 as a source of the trifluoromethylthio. This reaction system tolerates a broad range of functional groups to commendably achieve a high product yield and excellent stereoselectivity of E/Z.

  已经开发了在温和的反应条件下有效的铜（II）促进的反硝化三氟甲基硫醇化反应，用于乙烯基三氟甲基硫醚，以稳定的AgSCF 3作为三氟甲硫基的来源构建C乙烯基-SCF 3键。该反应体系可耐受各种官能团，从而可实现很高的产物收率和出色的E / Z立体选择性。
• Facile and Mild Access to Fluorescent Ladder-Type Indolo[3,2-a]carbazoles via Cascade Annulation
  作者：Wenteng Chen、Yongping Yu、Shuangrong Liu、You Wu、Zhimin Ying、Feng Luo、En Chen

  DOI：10.1055/s-0040-1706473

  日期：2021.3

  A set of fluorescent ladder-type indolo[3,2-a]carbazoles were rationally developed via cascade annulation of indoles and nitroolefins under mild reaction conditions. Diverse functional groups were tolerated. Moreover, structure–photophysical properties relationships (SPPR) of indolo[3,2-a]carbazoles were observed to be simply tuned by changing the electronic nature of the peripheral substituents.

  通过在温和反应条件下对吲哚和硝基烯烃进行级联环化反应，合理地开发了一组荧光梯形吲哚[3,2-a]咔唑。能够容忍多样的官能团。此外，观察到吲哚[3,2-a]咔唑的结构-光物理性质关系（SPPR）可以通过改变周围取代基的电子性质来简单调节。

• Ferrocene as a scaffold for effective bifunctional amine–thiourea organocatalysts
  作者：Wei Yao、Ming Chen、Xueying Liu、Ru Jiang、Shengyong Zhang、Weiping Chen

  DOI：10.1039/c4cy00199k

  日期：——

  This work demonstrates that ferrocene could be an excellent scaffold for chiral organocatalysts.

  这项工作表明，二茂铁可以作为手性有机催化剂的优秀支架。
• 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％。