m-Nitro-cinnamylbromid | 90725-55-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: m-Nitro-cinnamylbromid
• 英文别名: 1-(3-Bromoprop-1-enyl)-3-nitrobenzene
• CAS: 90725-55-6
• 化学式: C₉H₈BrNO₂
• 分子量: 242.072
• InChiKey: WVCOXGRCYMPXEK-UHFFFAOYSA-N

物化性质

• 沸点：
  321.2±30.0 °C(Predicted)
• 密度：
  1.557±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 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：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  m-Nitro-cinnamylbromid 在 水 、 sodium hydride 、 lithium chloride 作用下， 以 四氢呋喃 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 16.5h， 生成
  参考文献：
  名称：

  共轭α-取代的二烯酸的高度区域和对映选择性加氢。

  摘要：

  使用Trifer-Rh配合物首次实现了对共轭α-取代二烯酸的高度区域和对映选择性加氢，为合成手性α-取代的γ，δ-不饱和酸提供了一种简单的方法。DFT计算表明，形成N + H–O氢键相互作用可稳定过渡态，并且4,5-双键与Rh（III）中心的配位将促进还原消除过程。该氢化提供了沙比特利前体的克级合成。

  DOI：

  10.1021/acs.orglett.0c00915
• 作为产物：
  描述：

  3-nitrocinnamaldehyde 在 sodium tetrahydroborate 、 三溴化磷 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.5h， 生成 m-Nitro-cinnamylbromid
  参考文献：
  名称：

  Discovery of Potent Benzofuran-Derived Diapophytoene Desaturase (CrtN) Inhibitors with Enhanced Oral Bioavailability for the Treatment of Methicillin-Resistant Staphylococcus aureus (MRSA) Infections

  摘要：

  Blocking the staphyloxanthin biosynthesis process has emerged as a new promising antivirulence strategy. Previously, we first revealed that CrtN is a druggable target against infections caused by pigmented Staphylococcus aureus (S. aureus) and that naftifine was an effective CrtN inhibitor. Here, we identify a new type of benzofuran-derived CrtN inhibitor with submicromolar IC50 values that is based on the naftifine scaffold. The most potent analog, 5m, inhibits the pigment production of S. aureus Newman and three MRSA strains, with IC50 values of 0.38-5.45 nM, without any impact on the survival of four strains (up to 200 mu M). Notably, compound 5m (1 mu M) could significantly sensitize four strains to immune clearance and could effectively attenuate the virulence of three strains in vivo. Moreover, 5m was determined to be a weak antifungal reagent (MIC > 16 mu g/mL). Combined with good oral bioavailability (F = 42.2%) and excellent safety profiles, these data demonstrate that 5m may be a good candidate for the treatment of MRSA infections.

  DOI：

  10.1021/acs.jmedchem.5b01984

文献信息

• The ortho-Claisen Rearrangement. IV. The Rearrangement of X-Cinnamyl p-Tolyl Ethers¹
  作者：William N. White、Wilmer K. Fife

  DOI：10.1021/ja01479a026

  日期：1961.9
• Discovery of Potent Benzofuran-Derived Diapophytoene Desaturase (CrtN) Inhibitors with Enhanced Oral Bioavailability for the Treatment of Methicillin-Resistant <i>Staphylococcus aureus</i> (MRSA) Infections
  作者：Youxin Wang、Feifei Chen、Hongxia Di、Yong Xu、Qiang Xiao、Xuehai Wang、Hanwen Wei、Yanli Lu、Lingling Zhang、Jin Zhu、Chunquan Sheng、Lefu Lan、Jian Li

  DOI：10.1021/acs.jmedchem.5b01984

  日期：2016.4.14

  Blocking the staphyloxanthin biosynthesis process has emerged as a new promising antivirulence strategy. Previously, we first revealed that CrtN is a druggable target against infections caused by pigmented Staphylococcus aureus (S. aureus) and that naftifine was an effective CrtN inhibitor. Here, we identify a new type of benzofuran-derived CrtN inhibitor with submicromolar IC50 values that is based on the naftifine scaffold. The most potent analog, 5m, inhibits the pigment production of S. aureus Newman and three MRSA strains, with IC50 values of 0.38-5.45 nM, without any impact on the survival of four strains (up to 200 mu M). Notably, compound 5m (1 mu M) could significantly sensitize four strains to immune clearance and could effectively attenuate the virulence of three strains in vivo. Moreover, 5m was determined to be a weak antifungal reagent (MIC > 16 mu g/mL). Combined with good oral bioavailability (F = 42.2%) and excellent safety profiles, these data demonstrate that 5m may be a good candidate for the treatment of MRSA infections.
• Highly Regio- and Enantioselective Hydrogenation of Conjugated α-Substituted Dienoic Acids
  作者：Xian Liu、Song Liu、Quanjun Wang、Gang Zhou、Lin Yao、Qin Ouyang、Ru Jiang、Yu Lan、Weiping Chen

  DOI：10.1021/acs.orglett.0c00915

  日期：2020.4.17

  Highly regio- and enantioselective hydrogenation of conjugated α-substituted dienoic acids was realized for the first time using Trifer–Rh complex, providing a straightforward method for the synthesis of chiral α-substituted γ,δ-unsaturated acids. DFT calculations revealed N+H–O hydrogen bonding interaction is formed to stabilize the transition state and the coordination of 4,5-double bond to Rh(III)

  使用Trifer-Rh配合物首次实现了对共轭α-取代二烯酸的高度区域和对映选择性加氢，为合成手性α-取代的γ，δ-不饱和酸提供了一种简单的方法。DFT计算表明，形成N + H–O氢键相互作用可稳定过渡态，并且4,5-双键与Rh（III）中心的配位将促进还原消除过程。该氢化提供了沙比特利前体的克级合成。