1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene | 37629-51-9

• 物质功能分类: 有机原料
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene
• 英文别名: (E)-1-methoxy-4-(2-nitroprop-1-en-1-yl)benzene；(E)-1-methoxy-4-(2-nitroprop-1-enyl)benzene；(E)-1-(4'-methoxyphenyl)-2-nitropropene；1-(4-Methoxyphenyl)-2-nitropropene；1-methoxy-4-[(E)-2-nitroprop-1-enyl]benzene
• CAS: 37629-51-9
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: XQGFRDLMKKKSAH-BQYQJAHWSA-N

物化性质

• 熔点：
  45 °C
• 沸点：
  321.7±17.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 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：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene 在 10% palladium on active carbon 吡啶 、 盐酸 、 aluminum oxide 、 lithium aluminium tetrahydride 、 氢气 、 铁粉 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二甲基亚砜 为溶剂， 反应 100.25h， 生成 福莫特罗
  参考文献：
  名称：

  An efficient enantioselective synthesis of (R,R)-formoterol, a potent bronchodilator, using lipases

  摘要：

  0The potent beta(2)-adrenergic receptor agonist formoterol (R,R)-1 has been obtained in enantiomerically pure form by a convenient chemoenzymatic approach by coupling of epoxide (R)-6 with the unprotected primary amine (R)-9. Both chiral precursors have been prepared by enantiodifferentiation processes involving Pseudomonas cepacia (lipase PS) and Candida antarctica lipase (CALB), respectively. For the resolution of amine 9, we have found that utilization of triethylamine as non-reactive base enhances the reaction rate and the enantioselectivity of the process. The key coupling reaction of (R)-6 and (R)-9 has been conducted through derivatization of the amine with the labile trimethylsilyl group, which liberates the amino group of the resulting amino alcohol (R,R)-11 upon column chromatography purification. In this way, the overall approach is shorter than others previously described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00238-x
• 作为产物：
  描述：

  茴香烯 在 氘代吡啶 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 4.42h， 生成 1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene
  参考文献：
  名称：

  Photochemical Nitration by Tetranitromethane. Part XLII. Photolysis of Some 4-Methoxystyrene Derivatives with Tetranitromethane.

  摘要：

  The photochemical reaction of 4-methoxystyrene (2a) with tetranitromethane in dichloromethane gives the nitro-trinitromethyl adduct, 2-(4'-methoxyphenyl)-1-nitro-2-trinitromethylethane (1), which on chromatography on silica gel yields the (E)-nitroalkene, (E)-4'-methoxy-2-nitrostyrene (3); in acetonitrile solution adduct 1 is also the major product together with minor adducts. Similar reaction of trans-1-(4'-methoxyphenyl)-1-propene (2b) in dichloromethane gives exclusively the stereoisomeric nitro-trinitromethyl adducts, 1-(4'-methoxyphenyl)-2-nitro-1-trinitromethylpropanes 6 and 7, but in acetonitrile adduct 7 is the major product together with a small amount of adduct 6 and a mixture of minor adducts. The base-catalysed reactions of adducts 1 and 6 gave nitroalkenes (E)-4'-methoxy-2-nitrostyrene (3) and (E)-1-(4'-methoxyphenyl)-2-nitro-1-propene (8), respectively, but reaction of adduct 7 gave a product of unknown structure. Kinetic studies of the base-catalysed reactions of nitro-trinitromethyl adducts 1, 6 and 7, and a nitro-trinitromethyl adduct derived from naphthalene, cis-1-nitro-4-trinitromethyl-1,4-dihydronaphthalene, are reported. A mixture of (E)- and (Z)-4-methoxycinnamonitrile did not react on extended photolysis with tetranitromethane. The photochemical reactions of 4-methoxystyrenes 2a and 2b with tetranitromethane are assumed to proceed via a radical chain reaction mechanism.

  DOI：

  10.3891/acta.chem.scand.52-0745

文献信息

• Borrowing hydrogen: iridium-catalysed reactions for the formation of C–C bonds from alcohols
  作者：Phillip. J. Black、Gerta Cami-Kobeci、Michael G. Edwards、Paul A. Slatford、Michael K. Whittlesey、Jonathan M. J. Williams

  DOI：10.1039/b511053j

  日期：——

  Alcohols have been employed as substrates for C-C bond-forming reactions which involve initial activation by the temporary removal of hydrogen to form an aldehyde. The intermediate aldehyde is converted into an alkene via a Horner-Wadsworth-Emmons reaction, nitroaldol and aldol reactions. The 'borrowed hydrogen' is then returned to the alkene to form a C-C bond.

  醇已被用作CC键形成反应的底物，该反应涉及通过暂时除去氢以形成醛而进行的初始活化。中间体醛通过霍纳-沃兹沃思-埃蒙斯反应，硝基醛和醛醇反应转化为烯烃。然后将“借来的氢”返回到烯烃以形成CC键。
• Nitration of substituted styrenes with nitryl iodide
  作者：Wing-Wah Sy、Arnold W. By

  DOI：10.1016/s0040-4039(00)98431-4

  日期：1985.1

  Nitration of substituted styrenes by nitryl iodide, followed by treatment of the product with triethylamine, gives β-nitrostyrenes in good yield.

  用亚硝酰碘硝化取代的苯乙烯，然后用三乙胺处理产物，以良好的收率得到β-硝基苯乙烯。
• Novel dihydroquinolizinones for the treatment and prophylaxis of hepatitis B virus infection
  申请人：Hoffmann-La Roche Inc.

  公开号：US20150210682A1

  公开（公告）日：2015-07-30

  The invention provides novel compounds having the general formula: wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as described herein, compositions including the compounds and methods of using the compounds.

  这项发明提供了具有一般公式的新化合物： 其中R1、R2、R3、R4、R5和R6如本文所述，包括这些化合物的组合物和使用这些化合物的方法。
• [EN] NOVEL DIHYDROQUINOLIZINONES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION<br/>[FR] NOUVELLES DIHYDROQUINOLIZINONES POUR LE TRAITEMENT ET LA PROPHYLAXIE D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE B
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015113990A1

  公开（公告）日：2015-08-06

  The invention provides novel compounds having the general formula (I) wherein R1, R2 R3, R4, R5 and R6 are as described herein, compositions including the compounds and methods of using the compounds in the treatment of the hepatitis B virus.

  这项发明提供了具有一般式（I）的新化合物，其中R1、R2、R3、R4、R5和R6如本文所述，包括这些化合物的组合物以及在治疗乙型肝炎病毒方面使用这些化合物的方法。
• Clean five-step synthesis of an array of 1,2,3,4-tetra-substituted pyrroles using polymer-supported reagents
  作者：Marina Caldarelli、Jörg Habermann、Steven V. Ley

  DOI：10.1039/a809345h

  日期：——

  Polymer-supported reagents and other solid sequestering agents may be used to generate an array of 1,2,3,4-tetra-substituted pyrrole derivatives without any chromato-graphic purification step.

  聚合物支撑试剂及其他固态捕获剂可用于合成一系列1,2,3,4-四取代吡咯衍生物，无需任何色谱纯化步骤。