3-cyano-3-desoxy-morphine

• 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: 3-cyano-3-desoxy-morphine
• 英文别名: (4R,4aR,7S,7aR,12bS)-7-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-9-carbonitrile
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: PWWWEJXIZVBYHY-UKCJKJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-cyano-3-desoxy-morphine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、275.8 kPa 条件下， 反应 4.0h， 以100%的产率得到(4R,4aR,7S,7aR,12bS)-7-hydroxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-9-carbonitrile
  参考文献：
  名称：

  阿片受体新型高亲和力配体的合成

  摘要：

  制备了一系列新型高亲和力阿片受体配体，其中纳布啡、纳曲酮甲硫醚、6-去氧纳曲酮、氢吗啡酮和纳曲吲哚的酚羟基被羧酰胺基团取代，呋喃环开环形成相应的 4-羟基衍生物. 这些呋喃环“开放”衍生物对 μ 和 κ 受体显示出非常高的亲和力，而对 δ 的亲和力要低得多。观察到这些目标化合物比相应的环“闭合”羧酰胺具有更高的受体亲和力，这显着加强了我们关于羧酰胺基团生物活性构象的潜在药效团假设。

  DOI：

  10.1016/j.bmcl.2009.02.078
• 作为产物：
  描述：

  吗啡 在 四(三苯基膦)钯 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.25h， 生成 3-cyano-3-desoxy-morphine
  参考文献：
  名称：

  Microwave-Promoted Pd-Catalyzed Cyanation of Aryl Triflates:  A Fast and Versatile Access to 3-Cyano-3-desoxy-10-ketomorphinans

  摘要：

  [GRAPHICS]A methodology for the microwave-promoted conversion of triflates to the corresponding nitriles by using 8% equiv of Pd(Ph3P)(4) as the catalyst and 2.0 equiv of Zn(CN)(2) as the cyanide source has been developed. This method is highly efficient for the preparation of 3-cyano-3-desoxy10-ketomorphinans. The reaction was generally completed in 15 min at 200 degreesC and produced products in greater than 86% yields.

  DOI：

  10.1021/ol027256p

文献信息

• WO2006/52710
  申请人：——

  公开号：——

  公开（公告）日：——
• 4-HYDROXYBENZOMORPHANS
  申请人：RENSSELAER POLYTECHNIC INSTITUTE

  公开号：US20130231361A1

  公开（公告）日：2013-09-05

  4-Hydroxybenzomorphans containing carboxamide or thiocarboxamide at the 3-position are useful as analgesics, anti-diarrheal agents, anticonvulsants, antitussives and anti-addiction medications. A compound of formula is disclosed, as are pharmaceutically acceptable acid addition salts, such as acetic, benzenesulfonic (besylate), benzoic, camphorsulfonic, citric, ethenesulfonic, fumaric, gluconic, glutamic, hydrobromic, hydrochloric, isethionic, lactic, maleic, malic, mandelic, methanesulfonic, mucic, nitric, pamoic, pantothenic, phosphoric, succinic, sulfuric, tartaric acid or p-toluenesulfonic acid salts. These compounds are useful for the treatment of pain.
• US8680112B2
  申请人：——

  公开号：US8680112B2

  公开（公告）日：2014-03-25
• US8802655B2
  申请人：——

  公开号：US8802655B2

  公开（公告）日：2014-08-12
• Microwave-Promoted Pd-Catalyzed Cyanation of Aryl Triflates:  A Fast and Versatile Access to 3-Cyano-3-desoxy-10-ketomorphinans
  作者：Ao Zhang、John L. Neumeyer

  DOI：10.1021/ol027256p

  日期：2003.1.1

  [GRAPHICS]A methodology for the microwave-promoted conversion of triflates to the corresponding nitriles by using 8% equiv of Pd(Ph3P)(4) as the catalyst and 2.0 equiv of Zn(CN)(2) as the cyanide source has been developed. This method is highly efficient for the preparation of 3-cyano-3-desoxy10-ketomorphinans. The reaction was generally completed in 15 min at 200 degreesC and produced products in greater than 86% yields.