5,6,8,14-四去氢-3,6-二甲氧基-17-甲基吗喃-4-醇 | 6878-93-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 5,6,8,14-四去氢-3,6-二甲氧基-17-甲基吗喃-4-醇
• 英文名称: 3,6-dimethoxy-17-methyl-morphina-5,8-dien-4-ol
• 英文别名: Phi-dihydrothebaine；(1S,9R)-4,13-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,10,13-pentaen-3-ol
• CAS: 6878-93-9
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: UDBMORSDGOBDDA-BEFAXECRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6,8,14-四去氢-3,6-二甲氧基-17-甲基吗喃-4-醇 在 platinum(IV) oxide 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 95.0 ℃ 、101.33 kPa 条件下， 反应 2.66h， 生成 4-羟基-3-甲氧基-17-甲基吗喃-6-酮
  参考文献：
  名称：

  Improved Synthesis of Dihydrothebainone and Its 14 β-Epimer

  摘要：

  An improved synthesis for the preparation of diastereomerically pure dihydrothebainone (1) from thebaine (3) is reported. A 41% overall yield was realized over three steps via direct transformation of dihydrothebaine-Phi (4) to thebainone-A (6) with 6N HCl.

  DOI：

  10.1080/00397919808005110
• 作为产物：
  描述：

  蒂巴因 在 氨 、 sodium 作用下， 以99%的产率得到5,6,8,14-四去氢-3,6-二甲氧基-17-甲基吗喃-4-醇
  参考文献：
  名称：

  Improved Synthesis of Dihydrothebainone and Its 14 β-Epimer

  摘要：

  An improved synthesis for the preparation of diastereomerically pure dihydrothebainone (1) from thebaine (3) is reported. A 41% overall yield was realized over three steps via direct transformation of dihydrothebaine-Phi (4) to thebainone-A (6) with 6N HCl.

  DOI：

  10.1080/00397919808005110

文献信息

• Methods of producing nor-opioid and nal-opioid benzylisoquinoline alkaloids
  申请人：Antheia, Inc.

  公开号：US10738335B2

  公开（公告）日：2020-08-11

  A method of demethylizing an opioid to a nor-opioid is provided. The method comprises contacting an opioid with at least one enzyme. Contacting the opioid with the at least one enzyme converts the opioid to a nor-opioid. A method of converting a nor-opioid to a nal-opioid is provided. The method comprises contacting a nor-opioid with at least one enzyme. Contacting the nor-opioid with the at least one enzyme converts the nor-opioid to a nal-opioid.

  本发明提供了一种将阿片类药物去甲基化为非阿片类药物的方法。该方法包括将阿片类药物与至少一种酶接触。将阿片与至少一种酶接触可将阿片转化为去甲阿片。提供了一种将去甲阿片转化为正阿片的方法。该方法包括将去甲阿片与至少一种酶接触。将去甲阿片与至少一种酶接触可将去甲阿片转化为正阿片。
• The Morphine–Thebaine group of alkaloids. Part IV. The structure of the thebainone methines and of thebainone-C
  作者：K. W. Bentley、H. M. E. Cardwell

  DOI：10.1039/jr9550003245

  日期：——
• Small; Browning, Journal of Organic Chemistry, 1939, vol. 3, p. 628 Anm., 636
  作者：Small、Browning

  DOI：——

  日期：——
• METHODS OF PRODUCING NOR-OPIOID AND NAL-OPIOID BENZYLISOQUINOLINE ALKALOIDS
  申请人：Antheia, Inc.

  公开号：US20190144900A1

  公开（公告）日：2019-05-16

  A method of demethylizing an opioid to a nor-opioid is provided. The method comprises contacting an opioid with at least one enzyme. Contacting the opioid with the at least one enzyme converts the opioid to a nor-opioid. A method of converting a nor-opioid to a nal-opioid is provided. The method comprises contacting a nor-opioid with at least one enzyme. Contacting the nor-opioid with the at least one enzyme converts the nor-opioid to a nal-opioid.
• Improved Synthesis of Dihydrothebainone and Its 14 β-Epimer
  作者：Marian R. Davidson、Brian T. Gregg

  DOI：10.1080/00397919808005110

  日期：1998.2

  An improved synthesis for the preparation of diastereomerically pure dihydrothebainone (1) from thebaine (3) is reported. A 41% overall yield was realized over three steps via direct transformation of dihydrothebaine-Phi (4) to thebainone-A (6) with 6N HCl.