(E)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline | 104621-47-8

• 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: (E)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-acetyl-1,2,3,4-tetrahydro-6,7-dimethoxy-1-veratrylidene-isoquinoline；2-Acetyl-1,2,3,4-tetrahydro-6,7-dimethoxy-1-(3,4-dimethoxy-benzyliden)isochinolin；1-[(1E)-1-[(3,4-dimethoxyphenyl)methylidene]-6,7-dimethoxy-3,4-dihydroisoquinolin-2-yl]ethanone
• CAS: 104621-47-8
• 化学式: C₂₂H₂₅NO₅
• 分子量: 383.444
• InChiKey: UKWPGQNUELVLGE-VCHYOVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  3,4-二氢罂粟碱 、 乙酰氯 在 三乙胺 作用下， 生成 (E)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 、 (Z)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Asymmetric synthesis of isoquinoline alkaloids by homogeneous catalysis

  摘要：

  DOI：

  10.1021/ja00282a054

文献信息

• Piperazine derivatives useful as calmodolin inhibitors
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP0624584A1

  公开（公告）日：1994-11-17

  A compound represented by formula (I): wherein Q represents an aryl group, a heterocyclic group, a diarylmethyl group, an aralkyl group composed of an aryl group and an alkylene group, an alkyl group or a cycloalkyl group, in which the aryl group, heterocyclic group, and the aryl moiety of the diarylmethyl group and aralkyl group may be substituted with one or more substituents; R represents a bicyclic, substituted, nitrogen-containing heterocyclic group or a substituted phenyl group, in which the nitrogen-containing heterocyclic group is composed of a 5-membered, substituted, aromatic or saturated ring containing one or two nitrogen atoms and a 6-membered ring; and Z represents an alkylene group, an alkenylene group, an alkylene group, a carbonyl group, an alkylene group containing a carbonyl group or an oxalyl group, or a salt thereof. The compound has calmodulin inhibitory activity and is useful as a treating agent for diseases in the circulatory organs or in the cerebral region which are caused by excessive activation of calmodulin.

  式 (I) 所代表的化合物： 其中 Q 代表芳基、杂环基、二芳甲基、由芳基和亚烷基组成的芳烷基、烷基或环 烷基，其中芳基、杂环基以及二芳甲基和芳烷基的芳基可被一个或多个取代基取代；R 代表双环、取代的含氮杂环基团或取代的苯基，其中含氮杂环基团由含有一个或两个氮原子的五元环、取代的芳香环或饱和环以及六元环组成；以及 Z 代表烯基、烯基、亚烷基、羰基、含有羰基的亚烷基或草酰基、 或其盐。该化合物具有钙调蛋白抑制活性，可用于治疗因钙调蛋白过度活化而引起的循环器官或脑部疾病。
• 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
• Piperazine derivatives useful as calmodulin inhibitors
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP0624584B1

  公开（公告）日：1998-08-19
• US5681954A
  申请人：——

  公开号：US5681954A

  公开（公告）日：1997-10-28
• 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.