1-(6,7-dimethoxy-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)ethanone | 5780-77-8

• 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-(6,7-dimethoxy-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)ethanone
• 英文别名: 2-acetyl-6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline；N-acetylsalsolidine；2-acetyl-6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydro-isoquinoline；1-Methyl-2-acetyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isochinolin；6,7-Dimethoxy-1-methyl-2-acetyl-1,2,3,4-tetrahydro-isochinolin；1-Methyl-2-acetyl-1,2,3,4-tetrahydro-6,7-dimethoxyisochinolin；1-(6,7-Dimethoxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-ethanone；1-(6,7-dimethoxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl)ethanone
• CAS: 5780-77-8
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: GGONZGHKXHEOPW-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  401.1±45.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  1-(6,7-dimethoxy-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)ethanone 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 120.0h， 以95%的产率得到6,7-二甲氧基-1-甲基-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  Rozwadowska; Sulima, Polish Journal of Chemistry, 2001, vol. 75, # 12, p. 1847 - 1852

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(3,4-二甲氧基苯乙基)乙酰胺 在 甲醇 、 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(6,7-dimethoxy-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)ethanone
  参考文献：
  名称：

  取代的1,2,3,4-四氢异喹啉的合成和收缩活性。

  摘要：

  由不同的酮酰胺以高产率合成了一系列不同的 1-单取代和 1,1-二取代 1,2,3,4-四氢异喹啉。我们开发了一种方便的方法，通过酮酰胺与有机镁化合物相互作用，然后在催化量的对甲苯磺酸（PTSA）存在下环化来合成二取代衍生物。根据羧酸或有机镁化合物的不同，在异喹啉骨架的 C-1 处引入了许多取代基。所获得的一些1,1-二烷基-1,2,3,4-四氢异喹啉具有针对豚鼠胃平滑肌制剂的收缩活性。

  DOI：

  10.3390/molecules16087019

文献信息

• Reduction of new substrates with a NADH model reduction of N-acyl-enamines: Mechanism and scope
  作者：Corine Leroy、Georges Dupas、Jean Bourguignon、Guy Quéguiner

  DOI：10.1016/s0040-4020(01)89323-6

  日期：1994.1

  Several examples of the successful reduction of N-acyl-enamine derivatives with a NADH model in the pyrrolo[2,3-b]pyridine series are given. It is shown, that the reduction is strongly dependent on electronic and geometrical factors. It appears that in general, the success of the reduction can be related to the ability of the magnesium ions to form a complex with the acyl group and with the enamine

  给出了用吡咯并[2,3-b]吡啶系列的NADH模型成功还原N-酰基-烯胺衍生物的几个例子。结果表明，减少量很大程度上取决于电子和几何因素。通常看来，还原的成功与镁离子与酰基和烯胺官能团形成配合物的能力有关。从这一观点出发，在此讨论α-乙酰氨基丙烯酸酯衍生物中烯胺官能团的还原，并讨论烯胺亚胺平衡的影响。
• Broadening in the scope of NADH models by using chiral and non chiral pyrrolo [2,3-bl pyridine derivatives.
  作者：V. Levacher、R. Benoit、J. Duflos、G. Dupas、J. Bourguignon、G. Queguiner

  DOI：10.1016/s0040-4020(01)90500-9

  日期：1991.1

  Non chiral and chiral NADH models in the pyrrolo [2,3-b] pyridine series have been synthesized. These reagents 1) allow reductions of substrates previously found to be non reducible with similar reagents, 2) can give either one enantiomer or the other during the reduction of a prochiral ketone depending on the experimental conditions, 3) can be used in the synthesis of chiral precursors of target molecules obtained with good enantiomeric excesses.
• 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.
• Czarnocki, Zbigniew; MacLean, David B.; Szarek, Walter A., Heterocycles, 1992, vol. 34, # 5, p. 943 - 953
  作者：Czarnocki, Zbigniew、MacLean, David B.、Szarek, Walter A.

  DOI：——

  日期：——
• DEVACHER;BENOIT, R.;DUFLOS, J.;DUPAS, G.;BOURGUIGNON, J.;QUEGUINER, G., TETRAHEDRON, 47,(1991) N, C. 429-440
  作者：DEVACHER、BENOIT, R.、DUFLOS, J.、DUPAS, G.、BOURGUIGNON, J.、QUEGUINER, G.

  DOI：——

  日期：——