(-)-N-Formyl-N-norreticuline | 72274-70-5

• 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: (-)-N-Formyl-N-norreticuline
• 英文别名: N-formylreticuline；(1R)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-3,4-dihydro-1H-isoquinoline-2-carbaldehyde
• CAS: 72274-70-5
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: QYKLIFNJBMPXQU-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-N-Formyl-N-norreticuline 在 高氯酸 、 硼烷 作用下， 生成 (-)-Reticuline-Perchloric Acid
  参考文献：
  名称：

  Expedient synthesis of racemic and optically active N-norreticuline and N-substituted and 6'-bromo-N-norreticulines

  摘要：

  DOI：

  10.1021/jo01292a008
• 作为产物：
  描述：

  4-(2-氨基乙基)-2-甲氧基苯酚 在 sodium tetrahydroborate 、 sodium methylate 、 三氯氧磷 作用下， 以 四氢呋喃 、 ammonium hydroxide 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 28.0h， 生成 (-)-N-Formyl-N-norreticuline
  参考文献：
  名称：

  Expedient synthesis of racemic and optically active N-norreticuline and N-substituted and 6'-bromo-N-norreticulines

  摘要：

  DOI：

  10.1021/jo01292a008

文献信息

• 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.
• Expedient synthesis of racemic and optically active N-norreticuline and N-substituted and 6'-bromo-N-norreticulines
  作者：Kenner Rice、Arnold Brossi

  DOI：10.1021/jo01292a008

  日期：1980.2