(S)-劳丹碱 | 3122-95-0

• 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
• 中文名称: (S)-劳丹碱
• 英文名称: (S)-(+)-1-(3-hydroxy-4-methoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: (+)-laudanidine；(S)-laudanine；laudanidine；5-((S)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-[1]isoquinolylmethyl)-2-methoxy-phenol；5-((S)-6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydro-[1]isochinolylmethyl)-2-methoxy-phenol；Rechtsdrehende 5-(6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydro-[1]isochinolylmethyl)-2-methoxy-phenol, (+)-Laudanidin；5-[[(1S)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-2-methoxyphenol
• CAS: 3122-95-0
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: MPYHGNAJOKCMAQ-INIZCTEOSA-N

物化性质

• 溶解度：
  soluble in No data available
• 熔点：
  175.75 °C
• 保留指数：
  2784.8

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-(+)-1-(4-bromobenzyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 、 (S)-劳丹碱 在 copper(l) iodide 、 N,N-二甲基甘氨酸 、 caesium carbonate 作用下， 以 甲乙醚 为溶剂， 反应 1.5h， 以51%的产率得到(+)-O-methylthalibrine
  参考文献：
  名称：

  从去质子化的α-氨基腈对映选择性合成四氢小pro碱和双苄基异喹啉生物碱

  摘要：

  在受控条件下，可以在α位置对6,7-二甲氧基-1,2,3,4-四氢异喹啉-1-腈进行定量去质子处理。它的烷基化直接提供了3,4-二氢异喹啉，它们可以用作制备各种生物碱的起始原料。在此描述了使用Noyori的不对称转移氢化法制备苄基异喹啉（+）-月桂啶，（+）-阿帕品碱和（+）-月桂碱以及四氢原小ber碱（-）-鸟嘌呤和（-）-四氢伪紫ep碱的方法。在Ullmann二芳基醚合成中，从非外消旋前体获得二聚生物碱（+）- O-甲基thalibrine和（+）-四甲基木酚胺。

  DOI：

  10.1021/jo201871c
• 作为产物：
  描述：

  (S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 生成 (S)-劳丹碱
  参考文献：
  名称：

  从去质子化的α-氨基腈对映选择性合成四氢小pro碱和双苄基异喹啉生物碱

  摘要：

  在受控条件下，可以在α位置对6,7-二甲氧基-1,2,3,4-四氢异喹啉-1-腈进行定量去质子处理。它的烷基化直接提供了3,4-二氢异喹啉，它们可以用作制备各种生物碱的起始原料。在此描述了使用Noyori的不对称转移氢化法制备苄基异喹啉（+）-月桂啶，（+）-阿帕品碱和（+）-月桂碱以及四氢原小ber碱（-）-鸟嘌呤和（-）-四氢伪紫ep碱的方法。在Ullmann二芳基醚合成中，从非外消旋前体获得二聚生物碱（+）- O-甲基thalibrine和（+）-四甲基木酚胺。

  DOI：

  10.1021/jo201871c

文献信息

• Spaeth; Burger, Monatshefte fur Chemie, 1926, vol. 47, p. 739
  作者：Spaeth、Burger

  DOI：——

  日期：——
• Frydman et al., Anales des la Asociacion Quimica Argentina, 1959, vol. 47, p. 99,108
  作者：Frydman et al.

  DOI：——

  日期：——
• Novel biogenetic pathways from (+)-reticuline. Three dimeric alkaloids: (+)-vanuatine, (+)-vateamine, and (+)-malekulatine
  作者：Jean Bruneton、Maurice Shamma、Robert D. Minard、Alan J. Freyer、Helene Guinaudeau

  DOI：10.1021/jo00170a016

  日期：1983.11
• The biosynthesis of papaverine proceeds via (S)-reticuline
  作者：Xu Han、Marc Lamshöft、Nadja Grobe、Xuan Ren、Anthony J. Fist、Toni M. Kutchan、Michael Spiteller、Meinhart H. Zenk

  DOI：10.1016/j.phytochem.2010.04.022

  日期：2010.8

  Papaverine is one of the earliest opium alkaloids for which a biosynthetic hypothesis was developed on theoretical grounds. Norlaudanosoline (=tetrahydropapaveroline) was claimed as the immediate precursor alkaloid for a multitude of nitrogen containing plant metabolites. This tetrahydroxylated compound was proposed to be fully O-methylated. The resulting tetrahydropapaverine should then aromatize to papaverine. In view of experimental data, this pathway has to be revised. Precursor administration to 8-day-old seedlings of Papaver followed by direct examination of the metabolic fate of the stable-isotope-labeled precursors in the total plant extract, without further purification of the metabolites, led to elucidation of the papaverine pathway in vivo. The central and earliest benzylisoquinoline alkaloid is not the tetraoxygenated norlaudanosoline, but instead the trihydroxylated norcoclaurine that is further converted into (S)-reticuline, the established precursor for poppy alkaloids. The papaverine pathway is opened by the methylation of (S)-reticuline to generate (S)-laudanine. A second methylation at the 3' position of laudanine leads to laudanosine, both known alkaloids from the opium poppy. Subsequent N-demethylation of laudanosine yields the known precursor of papaverine: tetrahydropapaverine. Inspection of the subsequent aromatization reaction established the presence of an intermediate, 1,2-dihydropapaverine, which has been characterized. The final step to papaverine is dehydrogenation of the 1,2-bond, yielding the target compound papaverine. We conclusively show herein that the previously claimed norreticuline does not play a role in the biosynthesis of papaverine. (C) 2010 Elsevier Ltd. All rights reserved.
• Host Cells and Methods for Oxidizing Aromatic Amino Acids
  申请人：The Regents of the University of California

  公开号：US20140134689A1

  公开（公告）日：2014-05-15

  The present invention provides for a method of producing an oxidation product of an aromatic amino acid in a genetically modified host cell. The method comprises culturing the genetically modified host cell under a suitable condition such that the culturing results in the genetically modified host cell producing oxidation product of an aromatic amino acid. The host cell comprises an enzyme capable of catalyzing the oxidation of aromatic amino acid. In some embodiments, the host cell is capable of biosynthesizing BH4 or MH4 from GTP.