1-(β-naphthyl)-2-nitro-1-propene | 59832-12-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(β-naphthyl)-2-nitro-1-propene
• 英文别名: 2-(2-nitro-1-propenyl)naphthalene；7-β-Nitropropenyl-1,2,3,4-tetrahydro-naphthalin；2-<2-Nitro-propenyl>-naphthalin；1-<2>Naphthyl-2-nitro-prop-1-en；1-(2-naphthyl)-2-nitropropene；2-(2-Nitroprop-1-enyl)naphthalene
• CAS: 59832-12-1
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: DTZVIBZSHDZFPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  1-(β-naphthyl)-2-nitro-1-propene 在 lithium aluminium tetrahydride 、 sodium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 以40%的产率得到1-methyl-2-(2-naphthyl)-ethylamine hydrochloride
  参考文献：
  名称：

  Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors

  摘要：

  A series of naphthylisopropylamine and N-benzyl-4-methylthioamphetamine derivatives were evaluated as monoamine oxidase inhibitors. Their potencies were compared with those of a series of amphetamine derivatives, to test if the increase of electron richness of the aromatic ring and overall size of the molecule might improve their potency as enzyme inhibitors. Molecular dockings were performed to gain insight regarding the binding mode of these inhibitors and rationalize their different potencies. In the case of naphthylisopropylamine derivatives, the increased electron-donating capacity and size of the aromatic moiety resulting from replacement of the phenyl ring of amphetamine derivatives by a naphthalene system resulted in more potent compounds. In the other case, extension of the arylisopropylamine molecule by N-benzylation of the amino group led to a decrease in potency as monoamine oxidase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.074
• 作为产物：
  描述：

  硝基乙烷 、 2-萘甲醛 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 1-(β-naphthyl)-2-nitro-1-propene
  参考文献：
  名称：

  铜（II）催化的1H-苯并[d]咪唑-2-硫醇催化硝基烯烃的硫代氨基苯甲酸合成苯并[4,5]咪唑并[2,1-b]噻唑

  摘要：

  已开发出一种铜（II）催化的β-硝基烯烃与1 H-苯并[ d ]咪唑-2-硫醇的硫胺化反应，用于合成苯并[4,5]咪唑并[2,1– b ]噻唑衍生物。通过连续的CN和CS键形成，可以高收率获得各种N稠合的苯并咪唑并噻唑衍生物。该方案也适用于β-取代的β-硝基烯烃，以提供2,3-二取代的苯并咪唑并噻唑。

  DOI：

  10.1002/adsc.201800393

文献信息

• Organocatalytic Michael addition of aldehydes to trisubstituted nitroolefins
  作者：Leilei Wang、Xiaojing Zhang、Dawei Ma

  DOI：10.1016/j.tet.2012.05.088

  日期：2012.9

  to be effective to catalyze the Michael addition of aldehydes to 3-substituted 3-nitroacrylates. The reaction provided syn,anti-Michael adducts with good diastereoselectivity and excellent enantioselectivity. Some β-aryl and α-methyl substituted nitroolefins also worked under these conditions, although prolonging reaction time was required. These adducts could be used for assembling 2,3,4-trisubstituted

  发现O -TMS保护的二苯基-脯氨醇和苯甲酸的组合可有效催化醛向3-取代的3-硝基丙烯酸酯的迈克尔加成。该反应提供了具有良好的非对映选择性和优异的对映选择性的顺式，抗迈克尔加合物。尽管需要延长反应时间，但某些β-芳基和α-甲基取代的硝基烯烃也可在这些条件下起作用。这些加合物可用于通过简单的氢化组装2,3,4-三取代的吡咯烷。
• An efficient [3+2] cycloaddition for the synthesis of substituted pyrazolo[1,5-c]quinazolines
  作者：Tao Wang、Ailong Shao、Haiyan Feng、Shuwu Yang、Meng Gao、Jun Tian、Aiwen Lei

  DOI：10.1016/j.tet.2015.03.019

  日期：2015.7

  and efficient [3+2] cycloaddition reaction between N-iminoquinazolinium ylide and nitroolefins was developed. From a synthetic point of view, this protocol represents an efficient way to pyrazolo[1,5-c]quinazolines derivatives.

  开发了N-亚氨基喹唑啉鎓叶立德和硝基烯烃之间简单有效的[3 + 2]环加成反应。从综合的观点来看，该方案代表了吡唑并[1，5- c ]喹唑啉衍生物的有效方法。
• Practical Syntheses of N-Acetyl (E)-β-Arylenamides
  作者：Wenjun Tang、Zhihua Cai、Guodu Liu、Guangjun Jiao、Chris Senanayake

  DOI：10.1055/s-0033-1339976

  日期：——

  facile and practical method for the preparation of (E)-β-arylenamides [(E)-N-(1-arylprop-1-en-2-yl]acetamides] has been developed by reductive acetylation of the corresponding oximes with iron(II) acetate as the reducing reagent. Employment of hexamethylphosphoramide as the solvent was found to be critical for the high E/Z selectivity. The methodology has been applied in efficient syntheses of a key

  摘要 通过用铁还原相应的肟，开发了一种简便实用的制备（E）-β-芳基酰胺[（E）-N-（1-芳基丙-1-烯-2-基]乙酰胺]的方法（II）乙酸盐作为还原剂发现使用六甲基磷酰胺作为溶剂对高E / Z选择性至关重要，该方法已用于通过不对称氢化有效合成坦索罗辛的关键手性中间体。 通过用铁还原相应的肟，开发了一种简便实用的制备（E）-β-芳基酰胺[（E）-N-（1-芳基丙-1-烯-2-基]乙酰胺]的方法（II）乙酸盐作为还原剂发现使用六甲基磷酰胺作为溶剂对高E / Z选择性至关重要，该方法已用于通过不对称氢化有效合成坦索罗辛的关键手性中间体。
• Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter
  作者：Sara Meninno、Chiara Volpe、Giorgio Della Sala、Amedeo Capobianco、Alessandra Lattanzi

  DOI：10.3762/bjoc.12.63

  日期：——

  An investigation on the stereoselective cascade sulfa-Michael/aldol reaction of nitroalkenes and commercially available 1,4-dithiane-2,5-diol to 3,4,5-substituted tetrahydrothiophenes, bearing a quaternary stereocenter, is presented. A secondary amine thiourea derived from (R,R)-1,2-diphenylethylamine was found to be the most effective catalyst when using trans-β-methyl-β-nitrostyrenes affording the heterocyclic products in good yields and moderate stereoselectivities.

  一项关于立体选择性串联磺酰-迈克尔/醛缩反应的研究结果被提出，该反应以硝基烯烃和市售的1,4-二硫代醚-2,5-二醇为底物，生成带有季碳立体中心的3,4,5-取代四氢噻吩。当使用反式-β-甲基-β-硝基苯乙烯时，由(R,R)-1,2-二苯乙胺衍生的二级胺硫脲被发现是最有效的催化剂，产物收率良好，立体选择性适中。
• Synthesis of 2,7,12,17-tetra-arylporphyrins, new sterically hindered porphyrins
  作者：Noboru Ono、Hisayuki Kawamura、Masahiro Bougauchi、Kazuhiro Maruyama

  DOI：10.1039/c39890001580

  日期：——

  Sterically hindered porphyrins with four bulky aryl groups in the β-positions are prepared by the reduction of ethyl 3-aryl-4-alkylpyrrole-2-carboxylate with LiAIH4 followed by treatment with an acid and an oxidizing agent.

  通过用LiAlH 4还原3-芳基-4-烷基吡咯-2-羧酸乙酯，然后用酸和氧化剂处理，可制得在β位具有四个庞大的芳基的受阻卟啉。