B/C-trans-3-methoxy-17-methyl-6-morphinanone | 55298-15-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: B/C-trans-3-methoxy-17-methyl-6-morphinanone
• 英文别名: 3-methoxy-17-methylisomorphinan-6-one；(14alpha)-3-Methoxy-17-methylmorphinan-6-one；(1S,9R,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one
• CAS: 55298-15-2
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: FCJHDGUWJDXJKI-NXHRZFHOSA-N

物化性质

• 熔点：
  94.5-95.5 °C
• 沸点：
  437.5±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  B/C-trans-3-methoxy-17-methyl-6-morphinanone 在 氢溴酸 作用下， 以89%的产率得到(4bS,8aS,9R)-3-hydroxy-11-methyl-8,8a,9,10-tetrahydro-5H-9,4b-(epiminoethano)phenanthren-6(7H)-one
  参考文献：
  名称：

  止痛麻醉剂。2. 8-烷基吗啡喃-6-。

  摘要：

  通过将二烷基铜酸锂共轭添加到相应的7,8-二氢-6-烷基中来制备一系列的8-烷基-3-甲氧基-17-甲基吗啡喃-6-（3C）和-异吗啡喃-6-酮（3T）。 2C和2T。这些17-甲基化合物是有效的镇痛药，并通过用环烷基甲基部分取代17-甲基而转化为混合的麻醉激动剂-拮抗剂7-10。8个取代基改变了观察到的活性类型。这些化合物之一，即17-（环丁基甲基）-3-羟基-8β-甲基吗啡喃-6-（10Ca）的激动剂与拮抗剂之比为0.1。化合物10Ca在大鼠中不支持或不引起依赖性。然而，该化合物似乎是吗啡依赖性猴子中的典型麻醉剂。

  DOI：

  10.1021/jm00176a013
• 作为产物：
  描述：

  (1R,9R)-4,13-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,10,13-pentaene 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 三氟乙酸 作用下， 生成 3-methoxy-17-methylmorphinan-6-one 、 B/C-trans-3-methoxy-17-methyl-6-morphinanone
  参考文献：
  名称：

  Novel opiates and antagonists. 5. 7-Carbethoxy-N-(cycloalkylmethyl)-3-hydroxymorphinan-6-ones and -isomorphinan-6-ones

  摘要：

  A direct conversion of deoxydihydrothebaine-phi (1) to 3-methoxymorphinan-6-one (3Ca) and its trans isomer 3Ta was achieved in excellent yield by the catalytic reduction of 1 in AcOH containing CF3COOH. Treatment of 3Ca or 3Ta with NaH and diethyl carbonate formed the corresponding 7-carbethoxy derivatives 4a which, on O-demethylation, furnished the 3-hydroxy compounds 4b. The analgesic N-methyl compounds 3 were converted to the 17-(cyclopropylmethyl) or 17-(cyclobutylmethyl) derivatives 6--8. Two of these compounds, one in the cis (7Ca) and the other in the trans (7Ta) series, showed mixed agonist/antagonist activity in the pentazocine range.

  DOI：

  10.1021/jm00350a020

文献信息

• Novel opiates and antagonists. 6. 7-Alkyl-6,7-didehydromorphinans
  作者：James Quick、Patricia Herlihy、John F. Howes

  DOI：10.1021/jm00371a013

  日期：1984.5

  A method for preparing a variety of 7-alkyl-6,7- didehydromorphinans from the corresponding 6- morphinanones is described. The key intermediates in this sequence are the 7-formyl derivatives. The two epimeric B/C-trans-7-(1- hydroxypentyl ) morphinans ( 16a ,b) are stereochemically similar to the endo- ethanotetrahydrooripavines and are extremely potent in the mouse writhing test. The corresponding B/C-cis -7-(1- hydroxypentyl ) morphinans are inactive in this test.
• Sawa, Yoshiro K.; Kobayashi, Masaaki; Tada, Haruhiko, Heterocycles, 1984, vol. 22, # 11, p. 2575 - 2579
  作者：Sawa, Yoshiro K.、Kobayashi, Masaaki、Tada, Haruhiko

  DOI：——

  日期：——
• US4423221A
  申请人：——

  公开号：US4423221A

  公开（公告）日：1983-12-27
• US4454141A
  申请人：——

  公开号：US4454141A

  公开（公告）日：1984-06-12
• Novel opiates and antagonists. 5. 7-Carbethoxy-N-(cycloalkylmethyl)-3-hydroxymorphinan-6-ones and -isomorphinan-6-ones
  作者：Patricia Herlihy、Haldean C. Dalzell、John F. Howes、Raj K. Razdan

  DOI：10.1021/jm00350a020

  日期：1982.8

  A direct conversion of deoxydihydrothebaine-phi (1) to 3-methoxymorphinan-6-one (3Ca) and its trans isomer 3Ta was achieved in excellent yield by the catalytic reduction of 1 in AcOH containing CF3COOH. Treatment of 3Ca or 3Ta with NaH and diethyl carbonate formed the corresponding 7-carbethoxy derivatives 4a which, on O-demethylation, furnished the 3-hydroxy compounds 4b. The analgesic N-methyl compounds 3 were converted to the 17-(cyclopropylmethyl) or 17-(cyclobutylmethyl) derivatives 6--8. Two of these compounds, one in the cis (7Ca) and the other in the trans (7Ta) series, showed mixed agonist/antagonist activity in the pentazocine range.