[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-propyl-amine | 54979-13-4

• 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: [1-(4-Bromo-phenyl)-meth-(E)-ylidene]-propyl-amine
• 英文别名: p-Bromobenzylidene-propyl-amine；1-(4-bromophenyl)-N-propylmethanimine
• CAS: 54979-13-4
• 化学式: C₁₀H₁₂BrN
• 分子量: 226.116
• InChiKey: DAKVGMUXIVYXHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [1-(4-Bromo-phenyl)-meth-(E)-ylidene]-propyl-amine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以2.16 g的产率得到N-(4-溴苄基)-1-丙胺
  参考文献：
  名称：

  Preparation of Benzolactams by Pd(OAc)₂-Catalyzed Direct Aromatic Carbonylation

  摘要：

  We developed a new method for Pd(II)-catalyzed direct aromatic carbonylation in a phosphine-free catalytic system using Pd(OAc)2 and Cu(OAc)2 in an atmosphere of CO gas containing air. The carbonylation proceeded with ortho-palladation, inducing a remarkable site selectivity to afford a variety of five- or six-membered benzolactams from secondary omega-arylalkylamines, such as N-alkylbenzylamines or N-alkylphenethylamines.

  DOI：

  10.1021/ja045342+
• 作为产物：
  描述：

  对溴苯甲醛 在 N-氯代丁二酰亚胺 、 ammonium acetate 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 trans-2-(4-bromophenyl)-3-nitro-1-propylaziridine 、 [1-(4-Bromo-phenyl)-meth-(E)-ylidene]-propyl-amine
  参考文献：
  名称：

  得到硝基烯烃的直接氮杂环丙烷ñ -烷基- Ç -nitroaziridines和随后的路易斯酸介导的异构化，以β-Nitroenamines

  摘要：

  的温和和高度非对映一锅合成反式- ñ -烷基- Ç -nitroaziridines是通过用脂族胺和硝基烯烃的实现Ñ氯琥珀酰亚胺。用路易斯酸处理所获得的氮丙啶类化合物导致容易的开环反应，伴随着重排和异构化为官能化的（Z）-β-亚硝胺。

  DOI：

  10.1021/acs.orglett.7b02724

文献信息

• A Latent Reaction in a Model GFP Chromophore Revealed upon Confinement: Photohydroxylation of <i>ortho</i>-Halo Benzylidene-3-methylimidazolidiones via an Electrocylization Process
  作者：Shampa R. Samanta、José P. Da Silva、Anthony Baldridge、Laren M. Tolbert、V. Ramamurthy

  DOI：10.1021/ol5013058

  日期：2014.6.20

  Excited state behavior of halogen substituted model GFP chromophores was investigated in an acetonitrile solution and in a confined environment provided by an octa acid capsule in water. Of the ortho, meta, and para halogen substituted GFP chromophores only the ortho compounds gave a new product resulting from an unprecedented photosubstitution of halogens by the hydroxyl group. This unusual reaction

  在乙腈溶液中以及在辛酸胶囊在水中提供的密闭环境中，研究了卤素取代的GFP型发色团的激发态行为。在邻位，间位和对位卤素取代的GFP生色团中，仅邻位化合物会产生新产物，这是由于卤素通过羟基空前的光解而产生的。这种不寻常的反应凸显了密闭空间在实现某些无法实现的光反应中的重要性。
• Separation of Ring Polar and Resonance Effects on the Rate Constants for Uncatalyzed N-Arylidenepropylamine Formation in Methanol
  作者：Jean Toullec、Didier Milin

  DOI：10.1021/jo00089a033

  日期：1994.5

  Rate constants are reported for the reaction of a series of 19 ring-substituted benzaldehydes with propylamine in methanol and in O-d-methanol at different temperatures and of three of them with 2-methoxyethylamine and 2,2-dimethoxyethylamine. The large direct solvent kinetic isotope effects (KSIE) (2.1-2.9), as well as the Delta H* (4.7-7.6 kcal mol(-1)) values vary smoothly with substituent. Delta S* (ca. -45 cal mol(-1) K-1) is almost independent of substituent. These data indicate that there in no change in the rate-limiting step, and since the large KSIE and \Delta S*\ can be related to significant solvation of the leading OH- group at the transition state, they agree with a mechanism involving cu-amino alcohol formation in a fast preequilibrium followed by rate-limiting OH- detachment yielding iminium ions. When corrected for parallel hemiacetal formation, the second-order rate constants are accounted for by the Young-Jencks equation with p(n) = 0.08 and p(r) = 0.57, this equation allowing a separation of the direct resonance effects from the polar effects of the substituted ring. The very low p(n) value indicates that the polar effects for the rate-limiting OH- detachment are almost compensated by those on the constant of the alpha-amino alcohol-formation preequilibrium. In contrast, the relatively large p(r) coefficient, which means that the overall rate constants depend almost exclusively on resonance, is due to predominance of the direct resonance effects on the preequilibrium. The KSIE and Delta S* data, as well as the beta(nucl) parameters (close to unity) observed when the reacting amine was changed (slopes of the straight lines obtained by plotting the logarithm of the rate constants vs the pK(a) of the ammonium ions) favor a late transition state. In contrast, the low p(r) value for the rate-limiting step (ca. -0.5) shows that the transition state is not iminium ion-like.
• Direct Aziridination of Nitroalkenes Affording <i>N</i>-Alkyl-<i>C</i>-nitroaziridines and the Subsequent Lewis Acid Mediated Isomerization to β-Nitroenamines
  作者：Feiyue Hao、Haruyasu Asahara、Nagatoshi Nishiwaki

  DOI：10.1021/acs.orglett.7b02724

  日期：2017.10.6

  A mild and highly diastereoselective one-pot synthesis of trans-N-alkyl-C-nitroaziridines was achieved by treatment of nitroalkenes with aliphatic amines and N-chlorosuccinimide. Treatment of the obtained aziridines with a Lewis acid resulted in a facile ring opening reaction, accompanied by rearrangement and isomerization into functionalized (Z)-β-nitroenamines.

  的温和和高度非对映一锅合成反式- ñ -烷基- Ç -nitroaziridines是通过用脂族胺和硝基烯烃的实现Ñ氯琥珀酰亚胺。用路易斯酸处理所获得的氮丙啶类化合物导致容易的开环反应，伴随着重排和异构化为官能化的（Z）-β-亚硝胺。
• Preparation of Benzolactams by Pd(OAc)₂-Catalyzed Direct Aromatic Carbonylation
  作者：Kazuhiko Orito、Akiyoshi Horibata、Takatoshi Nakamura、Harumi Ushito、Hideo Nagasaki、Motoki Yuguchi、Satoshi Yamashita、Masao Tokuda

  DOI：10.1021/ja045342+

  日期：2004.11.1

  We developed a new method for Pd(II)-catalyzed direct aromatic carbonylation in a phosphine-free catalytic system using Pd(OAc)2 and Cu(OAc)2 in an atmosphere of CO gas containing air. The carbonylation proceeded with ortho-palladation, inducing a remarkable site selectivity to afford a variety of five- or six-membered benzolactams from secondary omega-arylalkylamines, such as N-alkylbenzylamines or N-alkylphenethylamines.