1-(acetylmethyl)-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline | 1246260-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1-(acetylmethyl)-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-(3,3-dimethyl-2,4-dihydro-1H-isoquinolin-1-yl)propan-2-one
• CAS: 1246260-59-2
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: ZKURNIGGFCABRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二甲基苄基原醇 在 硫酸 、 palladium diacetate 、 溶剂黄146 、 硫脲 、 silver carbonate 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 1-(acetylmethyl)-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  通过Pd（II）催化的NH2定向将Michael受体插入C–H键中，然后进行NH2偶联的加成反应，制备取代的四氢异喹啉

  摘要：

  3,3-Disubstituted tetrahydroisoquinolines are prepared in one step from Michael acceptors and 2-phenylethylamines under Pd catalysis and Ag2CO3 as an oxidant. Presumably, activation of an ortho C-H bond of the aromatic ring with Pd(II) is directed by the primary amine to form a palladacycle. Insertion of the olefin, subsequent conjugated addition of the amine, and reductive elimination of Pd(0) affords the expected products. Silver carbonate is not necessary when 2-phenylethylamines are converted previously to N-benzoyloxy-2-phenylethylamines.

  DOI：

  10.1021/acs.organomet.6b00944

文献信息

• Reactivity toward CO of Eight-Membered Palladacycles Derived from the Insertion of Alkenes into the Pd–C Bond of Cyclopalladated Primary Arylalkylamines of Pharmaceutical Interest. Synthesis of Tetrahydrobenzazocinones, Ortho-Functionalized Phenethylamines, Ureas, and an Isocyanate
  作者：José-Antonio García-López、María-José Oliva-Madrid、Isabel Saura-Llamas、Delia Bautista、José Vicente

  DOI：10.1021/om300593x

  日期：2012.9.10

  arising from the insertion of the alkene into the Pd–C bond, [PdC,N-CH(R)CH2C6H2CH2CH2NH2-2,(OMe)2-4,5}(μ-Br)]2 (R = CO2Et (2a1), C(O)Me (2a2)) or [PdC,N-CH(C5H8)CHC6H2CH2CH2NH2-2,(OMe)2-4,5}(μ-Br)]2 (2a3). Complexes 2a and the phentermine homologues 2b react with CO to afford Pd(0) and (1) tetrahydrobenzazocinones, the heterocycles resulting from CO insertion into the Pd–C bond and C–N coupling

  由高藜芦胺衍生的邻位金属络合物[Pd C，N -C 6 H 2 CH 2 CH 2 NH 2 -2，（OMe）2 -4,5}（μ-Br）] 2（1a）与乙基反应丙烯酸酯，甲基乙烯基酮或2-降冰片烯，生成由烯烃插入Pd-C键中形成的二聚体复合物[Pd C，N -CH（R）CH 2 C 6 H 2 CH 2 CH 2 NH 2 -2，（OMe）2 -4,5}（μ-Br）] 2（R = CO 2 Et（2a1），C（O）Me（2a2））或[Pd C，N -CH（C 5 H 8）CHC 6 H 2 CH 2 CH 2 NH 2 -2，（OMe）2 -4,5}（μ -Br）] 2（2a3）。配合物2a和芬特明同系物2b与CO反应生成Pd（0）和（1）四氢苯并甲酮，是由CO插入Pd-C键和C-N偶联产生的杂环；（2）非天然氨基酸衍生物，是由CO插入和取决于起始环palpalated化合物的
• Eight-Membered Palladacycles Derived from the Insertion of Olefins into the Pd−C Bond of Ortho-Palladated Pharmaceuticals Phenethylamine and Phentermine. Synthesis of Stable Heck-Type Intermediates Containing Accessible β-Hydrogens and Its Use in the Synthesis of 2-Styrylphenethylamines, Tetrahydroisoquinolines, and Eight-Membered Cyclic Amidines
  作者：José Vicente、Isabel Saura-Llamas、José-Antonio García-López、Delia Bautista

  DOI：10.1021/om100738z

  日期：2010.10.11

  the product of its insertion into the Pd−C bond, [PdC,N-CH(R′)CH2C6H4CH2CR2NH2-2}(μ-X)]2 (olefin = CH2═CHR′; R = H, X = Br, R′ = C(O)Me (1a), CO2Et (1c); R = Me, X = Cl, R′ = C(O)Me (1b), CO2Et (1d)) and [PdC,N-CH(C5H8)CHC6H4(CH2CMe2NH2)-2}(μ-Cl)]2 (olefin = norbornene, C5H8; 1e) or (2) the decomposition products of 1, i.e., Pd(0) and the complexes containing the arylated olefin, trans-[PdX2(NH2CR2CH2C6H4CH═CHPh-2)2]

  衍生自苯乙胺和芬特明的邻位金属配合物，[Pd（C，N -C 6 H 4 CH 2 CR 2 NH 2 -2）（μ-X）] 2（R = H，X = Br（A）; R = Me，X = Cl（B）），与烯烃反应，得到（1）其插入Pd-C键的产物[Pd C，N -CH（R'）CH 2 C 6 H 4 CH 2 CR 2 NH 2 -2}（μ-X）] 2（烯烃= CH 2 = CHR'; R = H，X = Br的，R'= C（O）Me（1A），CO 2Et（1c）; R = Me，X = Cl，R'= C（O）Me（1b），CO 2 Et（1d））和[Pd C，N -CH（C 5 H 8）CHC 6 H 4（CH 2 CMe 2 NH 2）-2}（μ-Cl）] 2（烯烃=降冰片烯，C 5 H 8；1e）或（2）1的分解产物，即Pd（0）和含有芳基化烯烃的配合物，反式-[PdX 2（NH 2
• Preparation of Substituted Tetrahydroisoquinolines by Pd(II)-Catalyzed NH₂-Directed Insertion of Michael Acceptors into C–H Bonds Followed by NH₂-Conjugated Addition
  作者：Andrea Mancinelli、Carla Alamillo、Joan Albert、Xavier Ariza、Haizea Etxabe、Jaume Farràs、Jordi Garcia、Jaume Granell、F. Javier Quijada

  DOI：10.1021/acs.organomet.6b00944

  日期：2017.2.27

  3,3-Disubstituted tetrahydroisoquinolines are prepared in one step from Michael acceptors and 2-phenylethylamines under Pd catalysis and Ag2CO3 as an oxidant. Presumably, activation of an ortho C-H bond of the aromatic ring with Pd(II) is directed by the primary amine to form a palladacycle. Insertion of the olefin, subsequent conjugated addition of the amine, and reductive elimination of Pd(0) affords the expected products. Silver carbonate is not necessary when 2-phenylethylamines are converted previously to N-benzoyloxy-2-phenylethylamines.