5-Brom-4-hydroxy-3-methoxy-β-nitrostyrol | 54737-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-Brom-4-hydroxy-3-methoxy-β-nitrostyrol
• 英文别名: (E)-2-bromo-6-methoxy-4-(2-nitrovinyl)phenol；5-bromovanillin nitrostyrene；6-bromo-2-methoxy-4-(2t-nitro-vinyl-(1r))-phenol；6-Brom-2-methoxy-4-(2t-nitro-vinyl-(1r))-phenol；trans-5-Brom-β-nitro-4-hydroxy-3-methoxy-styrol；1-(5-Bromo-4-hydroxy-3-methoxyphenyl)-2-nitroethene；2-bromo-6-methoxy-4-[(E)-2-nitroethenyl]phenol
• CAS: 54737-24-5
• 化学式: C₉H₈BrNO₄
• 分子量: 274.071
• InChiKey: VJLCVLQWILPELK-NSCUHMNNSA-N

物化性质

• 沸点：
  357.8±42.0 °C(Predicted)
• 密度：
  1.658±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  5-Brom-4-hydroxy-3-methoxy-β-nitrostyrol 在 吡啶 、 盐酸 、 汞 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 1.03h， 生成 1-(5-Brom-4-O-ethoxycarbonyl-3-methoxy-phenyl)-2-aminoethan
  参考文献：
  名称：

  关于紫楝生物碱的合成，第 1 版：不对称二苯并 1,4-二恶英头部的表示

  摘要：

  从 2a 和 3a 开始，N-保护的苯乙胺 2 和 3 分别分六个步骤制备。2 与 3 的混合双 Ullmann 反应生成不对称的二苯并 - 1,4 - 二恶英衍生物 K。由于具有选择性可去除的胺保护基团，这适用于楝树生物碱 1a-1d 的结构-选择性合成。

  DOI：

  10.1002/ardp.19893220805
• 作为产物：
  描述：

  香草醛 在 ammonium acetate 、 溴 作用下， 以 四氯化碳 、 氯仿 、 溶剂黄146 为溶剂， 反应 17.0h， 生成 5-Brom-4-hydroxy-3-methoxy-β-nitrostyrol
  参考文献：
  名称：

  Chemoselective Zinc/HCl Reduction of Halogenated β-Nitrostyrenes: Synthesis of Halogenated Dopamine Analogues

  摘要：

  A detailed account regarding the synthesis of 2- and 5-halogenated dopamine is given. The key step is a chemoselective reduction of a nitrostyrene by Zn/HCl at 0 degrees C. These conditions represent a simple, low-cost alternative to reduction by water-sensitive hydride donors and two-step procedures. Under these conditions, aryl fluoride, chloride, and bromide groups are stable. However, iodine undergoes significant reductive dehalogenation.

  DOI：

  10.1055/s-0034-1379481

文献信息

• Assessing the Relationship between Personal Particulate and Gaseous Exposures of Senior Citizens Living in Baltimore, MD
  作者：Jeremy A. Sarnat、Petros Koutrakis、Helen H. Suh

  DOI：10.1080/10473289.2000.10464165

  日期：2000.7

  We conducted a multi-pollutant exposure study in Baltimore, MDI in which 15 non-smoking older adult subjects (>64 years old) wore a multi-pollutant sampler for 12 days during the summer of 1998 and the winter of 1999. The sampler measured simultaneous 24-hr integrated personal exposures to PM2.5, PM10, SO42-, O-3, NO2, SO2, and exhaust-related VOCs.Results of this study showed that longitudinal associations between ambient PM2.5 concentrations and cofresponding personal exposures tended to be high in the summer (median Spearman's r = 0.74) and low in the winter (median Spearman's r = 0.25). Indoor ventilation was an important determinant of personal PM2.5 exposures and resulting personal-ambient associations. Associations between personal PM2.5 exposures and corresponding ambient concentrations were strongest for well-ventilated indoor environments and decreased with ventilation. This decrease was attributed to the increasing influence of indoor PM2.5 sources. Evidence for this was provided by SO42- measurements, which ran be thought of as a tracer for ambient PM2.5. For SO42-, personal-ambient associations were strong even in poorly ventilated indoor environments, suggesting that personal exposures to PM2.5 of ambient origin are strongly associated with corresponding ambient concentrations. The results also indicated that the contribution of indoor PM2.5 sources to personal PM2.5 exposures was lowest when individuals spent the majority of their time in well-ventilated indoor environments.Results also indicate that the potential for confounding by PM2.5 co-pollutants is limited, despite significant correlations among ambient pollutant concentrations. In contrast to ambient concentrations, PM2.5 exposures were not significantly correlated with personal exposures to PM2.5-10, PM2.5 of non-ambient origin, O-3, NO2, and SO2. Since a confounder must be associated with the exposure of interest, these results provide evidence that the effects observed in the PM2.5 epidemiologic studies are unlikely to be due to confounding by the PM2.5 co-pollutants measured in this study.
• CONDENSATION OF VANILLIN SUBSTITUTION PRODUCTS WITH NITROMETHANE
  作者：L. CHAS. RAIFORD、DONALD E. FOX

  DOI：10.1021/jo01184a005

  日期：1944.3
• PACHALY, PETER;SCHAFER, MICHAEL, ARCH. PHARM., 322,(1989) N, C. 447-482
  作者：PACHALY, PETER、SCHAFER, MICHAEL

  DOI：——

  日期：——
• Chemoselective Zinc/HCl Reduction of Halogenated β-Nitrostyrenes: Synthesis of Halogenated Dopamine Analogues
  作者：Justin Maresh、Arthur Ralko、Tom Speltz、James Burke、Casey Murphy、Zachary Gaskell、JoAnn Girel、Erin Terranova、Conrad Richtscheidt、Mark Krzeszowiec

  DOI：10.1055/s-0034-1379481

  日期：——

  A detailed account regarding the synthesis of 2- and 5-halogenated dopamine is given. The key step is a chemoselective reduction of a nitrostyrene by Zn/HCl at 0 degrees C. These conditions represent a simple, low-cost alternative to reduction by water-sensitive hydride donors and two-step procedures. Under these conditions, aryl fluoride, chloride, and bromide groups are stable. However, iodine undergoes significant reductive dehalogenation.
• Zur Synthese von Tiliacora-Alkaloiden, 1. Mitt.: Darstellung des unsymmetrischen Dibenzo-1,4-dioxin-Kopfteils
  作者：Peter Pachaly、Michael Schäfer

  DOI：10.1002/ardp.19893220805

  日期：——

  Ausgehend von 2a und 3a werden über jeweils sechs Stufen die N‐geschützten Phenylethylamine 2 und 3 dargestellt. Die gemischte doppelte Ullmann‐Reaktion von 2 mit 3 führt zum unsymmetrischen Dibenzo‐1,4‐dioxin‐Derivat K. Dieses eignet sich aufgrund der selektiv abspaltbaren Amin‐Schutzgruppen zur konstitutionsselektiven Synthese der Tiliacora‐Alkaloide 1a–1d.

  从 2a 和 3a 开始，N-保护的苯乙胺 2 和 3 分别分六个步骤制备。2 与 3 的混合双 Ullmann 反应生成不对称的二苯并 - 1,4 - 二恶英衍生物 K。由于具有选择性可去除的胺保护基团，这适用于楝树生物碱 1a-1d 的结构-选择性合成。