4,5α-epoxy-3-methoxy-17-methyl-morphinan-6-one | 125-29-1

• 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: 4,5α-epoxy-3-methoxy-17-methyl-morphinan-6-one
• 英文别名: hydrocodone；Hydrocodon；(-)-dihydrocodeinone；Dihydrocodeinon；(4R,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• CAS: 125-29-1；50896-88-3；64520-24-7；74035-75-9
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: LLPOLZWFYMWNKH-NXHIVTLCSA-N

物化性质

• 沸点：
  461.4±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 包装等级：
  III
• 危险类别：
  6.1(b)
• WGK Germany：
  2
• 危险品运输编号：
  UN 1544

反应信息

• 作为反应物：
  描述：

  4,5α-epoxy-3-methoxy-17-methyl-morphinan-6-one 在 三溴化硼 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis and biological activity of 8β-substituted hydrocodone indole and hydromorphone indole derivatives

  摘要：

  The 8beta-unsubstituted and substituted analogues of hydrocodone indole and hydromorphone indole were synthesized and their binding affinities to opioid receptors were determined. Introduction of an 8beta-methyl group into the indolomorphinan nucleus increased affinity at all opioid receptors. 6,7-Dehydro-4,5alpha-epoxy-8beta-methyl-6,7,2',3'-indolomorphinan (9) was found to be a delta antagonist with subnanomolar affinity (0,7 nM) for the delta-opioid receptor, and to have good delta-selectivity (mu/delta = 322). Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00689-8
• 作为产物：
  描述：

  codeinone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 4,5α-epoxy-3-methoxy-17-methyl-morphinan-6-one
  参考文献：
  名称：

  Synthesis and biological activity of 8β-substituted hydrocodone indole and hydromorphone indole derivatives

  摘要：

  The 8beta-unsubstituted and substituted analogues of hydrocodone indole and hydromorphone indole were synthesized and their binding affinities to opioid receptors were determined. Introduction of an 8beta-methyl group into the indolomorphinan nucleus increased affinity at all opioid receptors. 6,7-Dehydro-4,5alpha-epoxy-8beta-methyl-6,7,2',3'-indolomorphinan (9) was found to be a delta antagonist with subnanomolar affinity (0,7 nM) for the delta-opioid receptor, and to have good delta-selectivity (mu/delta = 322). Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00689-8

文献信息

• Heterogeneous Ruthenium Metal Catalyst for the Production of Hydrocodone, Hydromorphone or a Derivative Thereof
  申请人：GINDELBERGER David E.

  公开号：US20110071016A1

  公开（公告）日：2011-03-24

  The present disclosure generally relates to catalytic methods for producing opioid derivatives. More particularly, the present disclosure relates to the preparation of hydrocodone, hydromorphone, or a derivative thereof, by means of a conversion or an isomerization of codeine, morphine, or a derivative thereof, respectively, using a heterogeneous ruthenium metal catalyst.

  本公开涉及一般用于生产阿片类衍生物的催化方法。更具体地，本公开涉及通过使用异质钌金属催化剂，通过对可待因、吗啡或其衍生物进行转化或异构化的方式，制备羟考酮、羟吗啡或其衍生物。
• PROCESS FOR THE PREPARATION OF BENZHYDROCODONE HYDROCHLORIDE
  申请人：Noramco, Inc.

  公开号：US20180055836A1

  公开（公告）日：2018-03-01

  The invention is directed to processes for the preparation of benzhydrocodone hydrochloride. More particularly, the invention is directed to processes for a one-pot synthesis of benzhydrocodone hydrochloride of improved yield and/or purity.

  这项发明涉及苯羟考酮盐酸盐的制备过程。更具体地说，该发明涉及一种改进产率和/或纯度的苯羟考酮盐酸盐的一锅合成过程。
• METHODS FOR ONE-POT N-DEMETHYLATION/N-ACYLATION OF MORPHINE AND TROPANE ALKALOIDS
  申请人：Carroll Robert James

  公开号：US20090005565A1

  公开（公告）日：2009-01-01

  The present invention provides a method for the N-demethylation and/or N-acylation of an N-methylated heterocycle such as morphine alkaloids or tropane alkaloids. The method comprises reacting the heterocycle with an acylating agent in the presence of a metal catalyst.

  本发明提供了一种用于对N-甲基杂环化合物（如吗啡生物碱或曲梨生物碱）进行N-去甲基化和/或N-酰化的方法。该方法包括在金属催化剂存在下将杂环化合物与酰化剂反应。
• Novel analgesics and molecular rearrangements in the morphine–thebaine group. Part XXIV. 15,16-Didehydro-6,14-endo-etheno-6,7,8,14-tetrahydro-thebaines and -oripavines
  作者：D. I. Haddlesey、J. W. Lewis、P. A. Mayor、G. R. Young

  DOI：10.1039/p19720000872

  日期：——

  A series of 15,16-didehydro-compounds has been prepared by mercury(II) acetate dehydrogenation of 6,14-endo-ethenotetrahydro-thebaines and -oripavines. The reaction has also been applied to certain other morphine derivatives. Reduction of the didehydro-compounds with sodium borohydride in the presence of tritiated water gave the [15-3H]-derivatives.

  通过乙酸汞（II）对6,14-内-乙炔四氢-丁二酮和-奥帕文的乙酸汞（II）脱氢制备了一系列15,16-二氢化合物。该反应也已经应用于某些其他吗啡衍生物。具有在氚化水的存在下的硼氢化钠的二脱氢化合物的还原，得到[15- 3 H] -衍生物。
• METHOD OF PREPARING BUPRENORPHINE
  申请人：JOHNSON MATHEY PUBLIC LIMITED COMPANY

  公开号：US20140235860A1

  公开（公告）日：2014-08-21

  An improved process for preparing buprenorphine and a method for increasing the yield of buprenorphine or a derivative thereof.

  一种改进的制备丁丙诺啡的方法，以及增加丁丙诺啡或其衍生物产量的方法。