4-hydroxy-3-methoxy-17-methyl-14α-morphin-7-en-6-one | 596-59-8

• 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: 4-hydroxy-3-methoxy-17-methyl-14α-morphin-7-en-6-one
• 英文别名: 4-Hydroxy-3-methoxy-17-methyl-14α-morphin-7-en-6-on；(14alpha)-7,8-Didehydro-4-hydroxy-3-methoxy-17-methylmorphinan-6-one；(1S,9R,10S)-3-hydroxy-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
• CAS: 596-59-8
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: SLJDAVMWFVYEFI-LBTNJELSSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  475.4±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-methoxy-17-methyl-14α-morphin-7-en-6-one 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 2.08h， 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：

  5,6,8,14-四去氢-3,6-二甲氧基-17-甲基吗喃-4-醇 在 盐酸 作用下， 反应 0.58h， 以33%的产率得到4-hydroxy-3-methoxy-17-methyl-14α-morphin-7-en-6-one
  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

• Elimination of the 4-hydroxyl group of the alkaloids related to morphine—VIII
  作者：Y.K. Sawa、M. Horiuchi、K. Tanaka

  DOI：10.1016/0040-4020(65)80056-4

  日期：1965.1

  The Ullmann reaction of β-tetrahydrodesoxycodeine and the successive sodium—liquid ammonia reduction gave (−)-3-methoxy-N-methylisomorphinan in excellent yield. Similar reduction of the ketal of β-dihydrothebainone phenyl ether followed by the hydrolysis gave the desired (−)-3-methoxy-6-oxo-N-methylisomorphinan, whereas a similar sequence of reactions with β-thebainone-A phenyl ether gave (−)-3-me

  β-四氢脱氧可待因的Ullmann反应和连续的钠-液氨还原反应以极好的收率得到（-）-3-甲氧基-N-甲基异吗啡喃。β-二氢噻吩酮苯基醚的缩酮的相似还原反应，然后进行水解得到所需的（-）-3-甲氧基-6-氧代-N-甲基异吗啡喃，而与β-噻吩酮-A苯基醚的相似反应序列得到（ - ） - 3-甲氧基-6-氧代-N-甲基- Δ 7 -吗啡喃和对应的Δ 7 -isomorphinan衍生物。
• The Conversion of trans to cis Fusions of Rings II and III in the Morphine Series
  作者：Marshall Gates、Roger Helg

  DOI：10.1021/ja01098a036

  日期：1953.1
• REDUCTION STUDIES IN THE MORPHINE SERIES. VII. THEBAINE
  作者：LYNDON. SMALL、GEORGE L. BROWNING

  DOI：10.1021/jo01223a011

  日期：1939.1
• Schmid; Karrer, Helvetica Chimica Acta, 1950, vol. 33, p. 866,869
  作者：Schmid、Karrer

  DOI：——

  日期：——
• 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.