2-甲酰基-1,2,3,4-四氢-6,7-二甲氧基-1-甲基异喹啉 | 106275-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 2-甲酰基-1,2,3,4-四氢-6,7-二甲氧基-1-甲基异喹啉
• 英文名称: 2-formyl-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline
• 英文别名: 6,7-dimethoxy-1-methyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde
• CAS: 106275-11-0
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: NNLNOAGROPOFBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲酰基-1,2,3,4-四氢-6,7-二甲氧基-1-甲基异喹啉 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到(+/-)-carnegine
  参考文献：
  名称：

  A Highly Efficient Synthesis of 1-Methyl-, 1-Benzyl-, and 1-Phenyl-1,2,3,4-tetrahydroisoquinolines by a Modified Pummerer Reaction

  摘要：

  DOI：

  10.3987/com-97-s70
• 作为产物：
  描述：

  N-[1-(3,4-dimethoxyphenyl)ethyl]-N-(2-phenylsulfanylethyl)formamide 在 sodium tetrahydroborate 、 sodium periodate 、 三氟乙酸酐 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 苯 为溶剂， 反应 26.5h， 生成 2-甲酰基-1,2,3,4-四氢-6,7-二甲氧基-1-甲基异喹啉
  参考文献：
  名称：

  A Highly Efficient Synthesis of 1-Methyl-, 1-Benzyl-, and 1-Phenyl-1,2,3,4-tetrahydroisoquinolines by a Modified Pummerer Reaction

  摘要：

  DOI：

  10.3987/com-97-s70

文献信息

• Gold Particles Supported on Amino-Functionalized Silica Catalyze Transfer Hydrogenation of N-Heterocyclic Compounds
  作者：Beáta Vilhanová、Jeroen A. van Bokhoven、Marco Ranocchiari

  DOI：10.1002/adsc.201601147

  日期：2017.2.20

  supported on amino‐functionalized mesoporous silicate SBA‐15 are highly active in transfer hydrogenation of structurally diverse unsaturated N‐heterocyclic compounds. The heterocyclic ring is reduced selectively. The gold particles aggregate to a diameter of 4–5 nm in the presence of formic acid/triethylamine (hydrogen donor) during the first catalytic run. In subsequent cycles the nanoparticles maintain

  在这项工作中，我们证明了极小的金颗粒（d氨基官能化的介孔硅酸盐SBA-15上支撑的= 0.6±0.2 nm）在结构多样的不饱和N杂环化合物的转移氢化中具有很高的活性。杂环被选择性地还原。在第一个催化运行过程中，在存在甲酸/三乙胺（氢供体）的情况下，金粒子聚集至4–5 nm的直径。在随后的循环中，纳米粒子保持其尺寸，产生了非常稳定的催化系统，该系统被回收了五次以上。相反，具有较大（约5–35 nm）金颗粒的类似SBA催化剂则没有活性。过量的甲酸还会导致氢化产物的甲酰胺衍生物形成，可以定量地对其进行甲酰化。十五种结构不同的底物，包括喹啉，异喹啉，喹喔啉，a啶，菲咯啉，喹唑啉和菲啶被氢化和去甲酰基化，以总收率> 90％得到胺产物。氘标记实验表明，与1,4加成反应相比，1,2加成反应随后形成的中间体歧化是优选的反应路径，这表明氢化金的参与。
• New Methods for the Preparation 2-Formyl-1,2,3,4-tetrahydroisoquinolines<i>via</i> <i>N</i>-Formyliminium Ions
  作者：Ludmil K. Lukanov、Athanas P. Venkov、Nikola M. Mollov

  DOI：10.1055/s-1987-28162

  日期：——

  N-Formyl-2-phenylethylamines react with different aldehydes in acidic medium giving good yields of 2-formyl-1,2,3,4-tetrahydroisoquinolines. In situ prepared N-formyl-2-phenylethylamine (from phenethylamines in formic acid as the reaction medium) can also be used for the synthesis of the title compounds.

  在酸性介质中，N-甲酰基-2-苯基乙胺与不同的醛类发生反应，生成 2-甲酰基-1,2,3,4-四氢异喹啉类化合物。 原位制备的 N-甲酰基-2-苯基乙胺（以苯乙胺为原料，以甲酸为反应介质）也可用于合成标题化合物。
• General asymmetric synthesis of isoquinoline alkaloids. Enantioselective hydrogenation of enamides catalyzed by BINAP-ruthenium(II) complexes
  作者：Masato Kitamura、Yi Hsiao、Masako Ohta、Masaki Tsukamoto、Tetsuo Ohta、Hidemasa Takaya、Ryoji Noyori

  DOI：10.1021/jo00081a007

  日期：1994.1

  In the presence of a small amount of RuX(2)[(R)- or (S)-BINAP] (X = anionic ligand) a wide range of (Z)-2-acyl-1-benzylidene-1,2,3,4-tetrahydroisoquinolines are hydrogenated to give the saturated products in nearly quantitative yields and in high (up to 100 %) optical yields. The enamide substrates are selectively prepared by N-acylation of the corresponding 1-benzylated 3,4-dihydroisoquinolines under suitable acylation conditions; some crystalline materials having low solubility are obtained by a second-order Z/E stereomutation technique utilizing the double-bond photolability and lattice energy effects. This asymmetric hydrogenation sets the key stereogenic center in a predictable manner, either R or S flexibly, at the C(1) position of the benzylated tetrahydroisoquinolines. The chiral products are converted by standard functional group modification to tetrahydropapaverine, laudanosine, tretoquinol, norreticuline, etc. Hydrogenation of the simple 1-methylene substrate is used fbr synthesis of salsolidine. This enantioselective hydrogenation is applied to the synthesis of morphine and its artificial analogues such as morphinans and benzomorphans of either chirality. A mnemonic device is presented for predicting the reactivity and enantiofacial selection of the BINAP-Ru catalyzed hydrogenation. Reaction with BINAP-Rh catalyst proceeds with a lower enantioselectivity and an opposite sense of asymmetric induction.
• Reductive Formylation of Isoquinoline Derivatives with Formamide and Synthesis of 2-Formyltetrahydroisoquinolines
  作者：Atanas P. Venkov、Ilian I. Ivanov

  DOI：10.1080/00397919808006842

  日期：1998.4

  Reductive formylation of isoquinoline derivatives as 3,4-dihydroisoquinolines 1, enamines and enamides of tetrahydroisoquinoline 2 and the reaction of 2-(2-acylphenyl)ethylamides 3 with formamide afforded the corresponding N-formyltetrahydroisoquinolines 4 and N-acyltetrahydroisoquinolines 5.
• LUKANOV, LUDMIL K.;VENKOV, ATHANAS P.;MOLLOV, NIKOLA M., SYNTHESIS,(1987) N 11, 1031-1032
  作者：LUKANOV, LUDMIL K.、VENKOV, ATHANAS P.、MOLLOV, NIKOLA M.

  DOI：——

  日期：——