1,2-dehydronorreticuline | 72258-91-4

• 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: 1,2-dehydronorreticuline
• 英文别名: 1,2-dihydronorreticuline；7-Hydroxy-6-methoxy-1-(3-hydroxy-4-methoxy-benzyl)-3,4-dihydro-isochinolin；3,4-Dihydro-7-hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-isochinolin；1-(3-hydroxy-4-methoxy-benzyl)-6-methoxy-3,4-dihydro-isoquinolin-7-ol；1-[(3-Hydroxy-4-methoxyphenyl)methyl]-6-methoxy-3,4-dihydroisoquinolin-7-ol
• CAS: 72258-91-4
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: QBKHZIPQAFQYOE-UHFFFAOYSA-N

物化性质

• 沸点：
  529.7±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  71.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-dehydronorreticuline 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 ammonium hydroxide 为溶剂， 生成 (-)-Norreticuline hydrochloride
  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 三氯氧磷 作用下， 以 乙腈 为溶剂， 生成 1,2-dehydronorreticuline
  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.
• Purification and properties of 1,2-dehydroreticuline reductase from Papaver somniferum seedlings
  作者：Wanchai De-Eknamkul、Meinhart H. Zenk

  DOI：10.1016/0031-9422(92)80020-f

  日期：1992.3
• SZANTAY, CSABA;BLASKO, GABOR;BEKE, DENESNE;DORNYEL, GABOR;PECHY, PETER
  作者：SZANTAY, CSABA、BLASKO, GABOR、BEKE, DENESNE、DORNYEL, GABOR、PECHY, PETER

  DOI：——

  日期：——
• AMANN, M.;NAGAKURA, NAOTAKA;ZENK, M. H.
  作者：AMANN, M.、NAGAKURA, NAOTAKA、ZENK, M. H.

  DOI：——

  日期：——
• AMANN, MANFRED;ZENK, MEINHART H., PHYTOCHEMISTRY, 26,(1987) N 12, 3235-3240
  作者：AMANN, MANFRED、ZENK, MEINHART H.

  DOI：——

  日期：——