(R)-(-)-O-methylarmepavine | 3423-02-7

• 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: (R)-(-)-O-methylarmepavine
• 英文别名: (S)-(-)-O-methylamepavine；(+)-O-Methylarmepavine；(S)-O-methylarmepavine；(S)-6,7-dimethoxy-1-(4-methoxy-benzyl)-2-methyl-1,2,3,4-tetrahydro-isoquinoline；(S)-6,7-Dimethoxy-1-(4-methoxy-benzyl)-2-methyl-1,2,3,4-tetrahydro-isochinolin；O-Methyl-N-methyl-armepavin；(1S)-6,7-dimethoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-3,4-dihydro-1H-isoquinoline
• CAS: 3423-02-7
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: LZJWNVLTWYMMDJ-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 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：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933499090

反应信息

• 作为产物：
  描述：

  汉防己甲素 在 氨 、 sodium 、 甲苯 作用下， 生成 (R)-(-)-O-methylarmepavine
  参考文献：
  名称：

  Fujita; Tomimatsu, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 1260,1266

  摘要：

  DOI：

文献信息

• Synthesis of (+)-<i>O</i>-Methylthalibrine by Employing a Stereocontrolled Bischler-Napieralski Reaction and an Electrochemically Generated Diaryl Ether
  作者：Yuki Kawabata、Yu Naito、Tsuyoshi Saitoh、Kohei Kawa、Toshio Fuchigami、Shigeru Nishiyama

  DOI：10.1002/ejoc.201301128

  日期：2014.1

  An efficient electrochemical four-step route was developed for the preparation of diaryl ether derivatives by using halogenation and dehalogenation processes in addition to electrochemical phenolic oxidation and reduction reactions. The synthesis of (+)-O-methylthalibrine was achieved by employing this strategy along with a stereoselective Bischler–Napieralski reaction.

  除了电化学酚类氧化和还原反应外，还开发了一种有效的电化学四步路线，用于通过卤化和脱卤过程制备二芳基醚衍生物。通过采用这种策略以及立体选择性 Bischler-Napieralski 反应，合成了 (+)-O-methylthalibrine。
• Alkaloids of Dehaasia triandra
  作者：Sheng-Teh Lu、Ian-Lih、Tsai Shiow-Plaw Leou

  DOI：10.1016/0031-9422(89)80062-7

  日期：1989.1

  Abstract Separation of the basic fraction from Dehaasia triandra afforded two new bisbenzylisoquinoline alkaloids, dehatridine and dehatrine, along with six known alkaloids, isocorydine, corytuberine, atheroline, nantenine, obaberine and a quaternary aporphine alkaloid, xanthoplanine ( 5 ).

  摘要 从 Dehaasia triandra 中分离碱性组分得到了两种新的双苄基异喹啉生物碱，dehatridine 和 dehatrine，以及六种已知的生物碱，isocoorydine、corytuberine、atheroline、nantenine、obaberine 和一种四元 aporphine hoplanine (x5)。
• Lewis acid-mediated nucleophilic alkylations on chiral [6,3a,4]oxadiazaindano[5,4-a]isoquinolines. Asymmetric synthesis of 1-alkyl substituted tetrahydroisoquinolines
  作者：Naoki Yamazaki、Hideaki Suzuki、Sakae Aoyagi、Chihiro Kibayashi

  DOI：10.1016/0040-4039(96)01337-8

  日期：1996.8

  Lewis acid-mediated nucleophilic alkylation of the chiral [6,3a,4]oxadiaza-indano[5,4-α]isoquinoline derivatives with various organometallic reagents leads to highly enantioselective synthesis of 1-alkyl substituted tetrahydroisoquinolines. This methodology was applied to the asymmetric synthesis of (−)-salsolidine and (+)-O-methylarmepavine.

  路易斯酸介导的手性[6,3a，4]恶二氮杂-茚满[5,4-α]异喹啉衍生物与各种有机金属试剂的亲核烷基化导致1-烷基取代的四氢异喹啉的高度对映选择性合成。该方法学应用于（-）-沙丁胺碱和（+）- O-甲基阿马帕藤的不对称合成。
• Enzymic control of stereochemistry among the bisbenzylisoquinoline alkaloids
  作者：Hélène Guinaudeau、Alan J. Freyer、Maurice Shamma、Kemal Hüsnü Can Başer

  DOI：10.1016/s0040-4020(01)88437-4

  日期：1984.1

  1 and (+)-tha1iphylline (6) have been isolated from Thalictrum minus var. microphyllum. Four rules are described which correlate the structures of Thalictrum bisbenzylisoquinolines with their stereochemistry at C-1 and C-1'. As a result, (+)-tha1rugosamine is shown to be identical with (+)-homoaromo1ine (14). (+)-Thalisamine and (+)-N'-norhernandezine are also identical and are represented by expression

  新的双苄基异喹啉（+）-tha1igrisine 1和（+）-tha1iphylline（6）已从Thalictrum minus var中分离出来。小叶。描述了四个规则，它们将解藻双苄基异喹啉的结构与其在C-1和C-1'处的立体化学相关联。结果，显示（+）-去氢氨基葡萄糖与（+）-高亚氨酸（14）相同。（+）-邻苯二甲胺和（+）-N'-去甲扁桃碱也相同，并由表达式18表示。该规则的唯一例外是（-）-异噻嗪（15）。
• Fujita; Murai, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 1043,1046
  作者：Fujita、Murai

  DOI：——

  日期：——