(E)-2-Benzoyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline | 104621-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (E)-2-Benzoyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-benzoyl-6,7-dimethoxy-1-veratrylidene-1,2,3,4-tetrahydro-isoquinoline；2-Benzoyl-6,7-dimethoxy-1-veratryliden-1,2,3,4-tetrahydro-isochinolin；(E)-2-Benzoyl-1-[(3,4-dimethoxyphenyl)methylene]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline；[(1E)-1-[(3,4-dimethoxyphenyl)methylidene]-6,7-dimethoxy-3,4-dihydroisoquinolin-2-yl]-phenylmethanone
• CAS: 104621-38-7
• 化学式: C₂₇H₂₇NO₅
• 分子量: 445.515
• InChiKey: GMKYVBRSWLJBBE-HYARGMPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (R)-((S)-2-benzoyl-6,7-dimethoxy-1,2-dihydroisoquinolin-1-yl)(3,4-dimethoxyphenyl)methyl benzoate 在 palladium on activated charcoal CuSO4-silica 、 氢气 作用下， 以 四氢呋喃 、 xylene 为溶剂， 25.0 ℃ 、709.27 kPa 条件下， 反应 5.0h， 生成 (E)-2-Benzoyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  捷径合成1-苄基-异喹啉的波美兰-弗里奇；短而有效的去甲古铜碱衍生物和罂粟碱的合成

  摘要：

  已经开发出一种新的方法，用于Pomeranz-Fritsch合成1-苄基1,2-二氢异喹啉，避免了牛或异戊烷的困扰。这些中间体可以还原成它们的1,2,3,4-四氢同类物或芳香化得到异喹啉，这是通过合成一些降冰片碱衍生物4 – 7和罂粟碱8来证明的。

  DOI：

  10.1016/s0040-4039(00)74327-9

文献信息

• Asymmetric synthesis of isoquinoline alkaloids by homogeneous catalysis
  作者：Ryoji. Noyori、Masako. Ohta、Yi. Hsiao、Masato. Kitamura、Tetsuo. Ohta、Hidemasa. Takaya

  DOI：10.1021/ja00282a054

  日期：1986.10
• 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.
• Cyanoacylation of 1-substituted isoquinolines and 3,4-dihydroisoquinolines
  作者：Michael A. G. Berg、Harry W. Gibson

  DOI：10.1021/jo00028a064

  日期：1992.1
• Gardent, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 247, p. 2010,2013
  作者：Gardent

  DOI：——

  日期：——
• Short-cut in the pomeranz-fritsch synthesis of 1-benzyl-isoquinolines; short and efficient syntheses of norrecticuline derivatives and of papaverine
  作者：Rolf Hirsenkorn

  DOI：10.1016/s0040-4039(00)74327-9

  日期：1991.4

  A new methodology for the Pomeranz-Fritsch synthesis of 1-benzyl-1,2-dihydroisoquinolines avoiding pavine or isopavine troubles, has been developed. These intermediates could be reduced to their 1,2,3,4-tetrahydro congeners or aromatized to give isoquinolines, as it was demonstrated by the synthesis of some norrecticuline derivatives 4 – 7 and of papaverin 8.

  已经开发出一种新的方法，用于Pomeranz-Fritsch合成1-苄基1,2-二氢异喹啉，避免了牛或异戊烷的困扰。这些中间体可以还原成它们的1,2,3,4-四氢同类物或芳香化得到异喹啉，这是通过合成一些降冰片碱衍生物4 – 7和罂粟碱8来证明的。