2-nitro-1-(2-methoxynaphthyl)propene | 156482-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-nitro-1-(2-methoxynaphthyl)propene
• 英文别名: (Z)-2-nitro-1-(2-methoxynaphthyl)propene；2-Nitro-1-(2-methoxy-1-naphthyl)propene；2-methoxy-1-(2-nitroprop-1-enyl)naphthalene
• CAS: 156482-77-8
• 化学式: C₁₄H₁₃NO₃
• mdl: MFCD16285475
• 分子量: 243.262
• InChiKey: QJQITLLGHILJOC-UHFFFAOYSA-N

物化性质

• 沸点：
  407.0±20.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 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：

  2-nitro-1-(2-methoxynaphthyl)propene 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 N-<1-methyl-2-(2-methoxynaphthyl)ethyl>trifluoroacetamide
  参考文献：
  名称：

  Design and Synthesis of New Naphthalenic Derivatives as Ligands for 2-[125I]Iodomelatonin Binding Sites

  摘要：

  New melatonin-like agents were designed from the frameworks of 2,5-dimethoxyphenethylamine, an important structural moiety for the 5-HT receptor, and (2-methoxynaphthyl)-ethylamine. The compounds were synthesized by classical methods and evaluated in binding assays with chicken brain membranes using 2-[I-125]iodomelatonin as the radioligand. Preliminary studies on the series of N-acyl-disubstituted phenethylamines showed the favorable role of the methoxy group in the ortho position of the side chain on the affinity for the receptor K-i = 8 +/- 0.2 nM) for N-[2-(2-methoxy-5-bromophenyl)ethyl]propionamide (3o). This effect was confirmed in a series of the naphthalene derivatives, a bioisosteric moiety of the indole ring, and several potent ligands for melatonin binding sites were prepared such as N-[2-(2-methoxynaphthyl)ethyl]propionamide (4b) (K-i = 0.67 +/- 0.05 nM) and N-[2-(2,7-dimethoxynaphthyl)ethyl]cyclopropylformamide (K-i = 0.05 +/- 0.004 nM) (4k). Structure-activity relationships are discussed with regard to melatonin and bioisosteric naphthalenic compound 2. The K-i value for 4b was affected to a similar extent to that of melatonin by GTP-gamma-S or Mn2+ in competition experiments, suggesting an agonist profile for this compound.

  DOI：

  10.1021/jm00012a004
• 作为产物：
  描述：

  硝基乙烷 、 2-甲氧基-1-萘醛 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以54%的产率得到2-nitro-1-(2-methoxynaphthyl)propene
  参考文献：
  名称：

  A Simple Unusual One-Step Conversion of Aromatic Aldehydes into Nitriles

  摘要：

  DOI：

  10.1055/s-1985-31253

文献信息

• Catalytic Kinetic Resolution by Enantioselective Aromatization: Conversion of Racemic Intermediates of the Barton–Zard Reaction into Enantioenriched 3‐Arylpyrroles
  作者：Sheng‐Cai Zheng、Qian Wang、Jieping Zhu

  DOI：10.1002/anie.201903589

  日期：2019.7

  Racemic 3,4‐dihydro‐2H‐pyrroles, hypothetical intermediates of the Barton–Zard reaction, were synthesized in a highly diastereoselective manner and fully characterized for the first time. Kinetic resolution of the dihydropyrroles with a quinine‐derived thiourea afforded the (+)‐3‐arylpyrrole products and recovered (+)‐3,4‐dihydro‐2H‐pyrroles with high efficiency (s‐factor up to 153). The resolved (+)‐3

  外消旋的3,4-二氢-2 H-吡咯是Barton-Zard反应的假设中间体，以高度非对映选择性的方式合成，并首次得到了充分表征。用奎宁衍生的硫脲对二氢吡咯进行动力学拆分，得到了（+）-3-芳基吡咯产物，并高效回收了（+）-3,4-dihydro-2 H-吡咯（s因子高达153）。分解后的（+）-3,4-二氢-2 H-吡咯随后用奎尼丁衍生的硫脲催化剂进行芳构化，从而制得具有出色的中心-手性手性转移的（-）-3-芳基吡咯。与公认的Barton-Zard机制相反，3,4-二氢-2 H的芳构化在双功能催化剂存在下的吡咯被认为是通过空前的顺序进行的，该顺序涉及同步 消除HNO 2和芳构化。
• Asymmetric Barton–Zard Reaction To Access 3-Pyrrole-Containing Axially Chiral Skeletons
  作者：Xiao-Long He、Hui-Ru Zhao、Xue Song、Bo Jiang、Wei Du、Ying-Chun Chen

  DOI：10.1021/acscatal.9b00767

  日期：2019.5.3

  α-isocyano substrates with various electron-withdrawing groups, under the catalysis of Ag2O and a cinchona-derived phosphine ligand, providing a robust approach to construct axially chiral 3-(hetero)aryl pyrroles with a substantial skeleton and functionality versatility. An alternative asymmetric phase transfer catalysis protocol was also demonstrated to be practical for the direct construction of axially

  开发有效而可靠的催化方案以获取阻转异构化合物，尤其是那些具有较低旋转势垒的五元杂芳基结构的阻转异构化合物，是一项艰巨的任务。在这里，我们通过采用从中心到轴的手性转移策略，通过使用具有β-邻位取代的（杂）芳基的α-取代的硝基烯烃和具有各种吸电子性的α-异氰基底物，揭示了一种空前的促熵选择性Barton-Zard反应，其通过中心-轴向手性转移策略进行。团，在Ag 2的催化下O和金鸡纳衍生的膦配体，提供了一种可靠的方法来构建具有大量骨架和功能多样性的轴向手性3-（杂）芳基吡咯。还证明了一种替代性的不对称相转移催化方案对于轴向手性双膦二氧化物的直接构建是可行的。另外，通常对于获得的阻转异构体观察到良好的构象稳定性，并且已经在高度立体选择性的正式[4 + 2]环加成反应中很好地证明了它们作为有价值的有机催化剂的潜在应用。
• Reactivity of four-membered cyclic nitrones in 1,3-cycloaddition reactions. X-Ray crystal structure of 7-(2,6-dichlorophenyl)-N,N-diethyloctahydro-6-methyl-1,3-dioxo-2-phenylazeto[1,2-b]pyrrolo[3,4-d]isoxazole-6-carboxamide
  作者：Peter J. S. S. van Eijk、Willem Verboom、Frank C. J. M. van Veggel、David N. Reinhoudt、Sybolt Harkema

  DOI：10.1002/recl.19881070308

  日期：——

  diethyl maleate yielded the corresponding azeto[1,2-b]pyrrolo[3,4-d]isoxazole derivatives, 8 and 9, respectively. The exclusive formation of the exo-conformation of the cycloadducts was unequivocally proven by X-ray analysis of 8a. Reaction of 2a with methyl 2-propenoate (methyl acrylate) and 3-buten-2-one (methyl vinyl ketone) gave regio- and stereoselectively the corresponding exo-5′-isoxazolidine

  四元环硝酮1和2与乙炔二羧酸二甲酯反应，生成相应的环加合物3,4。2a与苯乙炔反应后，获得5'-取代的异恶唑啉衍生物5。2a与丙酸甲酯的反应分别生成4'-和5'-环加合物δ，7和6的1：4混合物。的反应2a-c中与N-苯基马来酰亚胺和的图2a与马来酸二乙酯，得到相应azeto [1,2-b]吡咯并[3,4-d]异恶唑衍生物，8和9， 分别。Xa射线分析8a明确证明了环加合物的exo-构象的排他性形成。的反应图2a用甲基-2-丙烯酸酯（甲基丙烯酸酯）和3-丁烯-2-酮（甲基乙烯基酮），得到区域选择性和立体选择性地对应的外-5'-异恶唑烷cycloadducts，10和11，分别。环加合物的立体化学由1 H NMR数据推导。炔烃和烯烃双极性亲和剂均从空间较少受阻的一侧接近四元环硝酮，导致所获得的环加合物的（区域和）立体选择性形成。
• Arylalkyl (thio)amides
  申请人：Adir Et Compagnie

  公开号：US05604261A1

  公开（公告）日：1997-02-18

  A compound which is selected from those of formula (I) : ##STR1## in which A, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are as defined in the description, its optical isomers, and its addition salts thereof with a pharmaceutically-acceptable acid or base, and medicinal products containing the same which are useful for treating a disorder of the melatoninergic system.

  从公式（I）中选择的化合物：##STR1## 其中A，R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5和R.sub.6如描述中所定义，其光学异构体，以及其与药学上可接受的酸或碱的加合盐，以及包含其的药物制剂，用于治疗褪黑素系统疾病。
• Arylalkyl (thio) amides
  申请人：Adir et Compagnie

  公开号：US05464872A1

  公开（公告）日：1995-11-07

  A compound which is selected from those of formula (I): ##STR1## in which A, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are as defined in the description, its optical isomers, and its addition salts thereof with a pharmaceutically-acceptable acid or base, and medicinal products containing the same which are useful for treating a disorder of the melatoninergic system.

  一种从式(I)所示的化合物中选择的化合物：##STR1## 其中A、R.sub.1、R.sub.2、R.sub.3、R.sub.4、R.sub.5和R.sub.6如描述中所定义的那样，其光学异构体和与药用可接受酸或碱的加成盐，以及含有该化合物的药物制剂，用于治疗褪黑激素系统的疾病。