14-acetoxy-4,5α-epoxy-3-hydroxy-6β-[((2S)-2-hydroxy-4-carboxy-4-n-pentenyl)oxy]-17-(cyclopropylmethyl)morphinan γ-lactone | 141555-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 14-acetoxy-4,5α-epoxy-3-hydroxy-6β-[((2S)-2-hydroxy-4-carboxy-4-n-pentenyl)oxy]-17-(cyclopropylmethyl)morphinan γ-lactone
• 英文别名: [(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-9-hydroxy-7-[[(2S)-4-methylidene-5-oxooxolan-2-yl]methoxy]-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl] acetate
• CAS: 141555-41-1
• 化学式: C₂₈H₃₃NO₇
• 分子量: 495.573
• InChiKey: YGMJUEYNRVHCAT-OOXKPLBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  14-acetoxy-4,5α-epoxy-3-hydroxy-6β-[((2S)-2-hydroxy-4-carboxy-4-n-pentenyl)oxy]-17-(cyclopropylmethyl)morphinan γ-lactone 在 palladium on activated charcoal 甲醇 、 氢气 作用下， 以 乙醇 为溶剂， 反应 25.5h， 生成 4,5α-epoxy-3,14-dihydroxy-6β-<(2S,4S)-2-hydroxy-4-carboxy-n-pentoxy>-17-(cyclopropylmethyl)morphinan γ-lactone
  参考文献：
  名称：

  Electrophilic opioid ligands. Oxygen-tethered .alpha.-methylene-.gamma.-lactone, acrylate, isothiocyanate, and epoxide derivatives of 6.beta.-naltrexol

  摘要：

  O6-Ether derivatives of 6-beta-naltrexol in which the ether substituent includes various electrophilic groups have been synthesized in an effort to examine structure-activity requirements at the 6-beta-substituent for receptor affinity and irreversibility of binding in opioid receptor preparations. A series of tethered 6-beta-ethers having terminal epoxides, alpha-methylene-gamma-lactones, and an isothiocyanate group were prepared. The stereochemistry of the alpha-methylene-gamma-lactones was established by convergent synthesis of their reduction products from epoxides of known absolute stereochemistry. In general, the tested compounds showed comparable affinity and selectivity for the receptor subtypes. All were found with high affinity for mu-sites. The terminal epoxide ether diastereomers 8 and 9 were not bound irreversibly in the assay for total opioid receptors. The alpha-methylene-gamma-lactone diastereomers 10 and 11, and their O-14-acetyl precursors 20 and 21, respectively, varied in their irreversible effects, but where noted these effects were mu-site selective. Methacrylate ether 7 and isothiocyanate ether 12 were bound irreversibly at both mu- and delta-sites.

  DOI：

  10.1021/jm00091a005
• 作为产物：
  描述：

  4,5α-epoxy-3,14-dihydroxy-6β-(2,2-diethoxyethoxy)-17-(cyclopropylmethyl)morphinan 在 草酸 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 14-acetoxy-4,5α-epoxy-3-hydroxy-6β-[((2S)-2-hydroxy-4-carboxy-4-n-pentenyl)oxy]-17-(cyclopropylmethyl)morphinan γ-lactone
  参考文献：
  名称：

  Electrophilic opioid ligands. Oxygen-tethered .alpha.-methylene-.gamma.-lactone, acrylate, isothiocyanate, and epoxide derivatives of 6.beta.-naltrexol

  摘要：

  O6-Ether derivatives of 6-beta-naltrexol in which the ether substituent includes various electrophilic groups have been synthesized in an effort to examine structure-activity requirements at the 6-beta-substituent for receptor affinity and irreversibility of binding in opioid receptor preparations. A series of tethered 6-beta-ethers having terminal epoxides, alpha-methylene-gamma-lactones, and an isothiocyanate group were prepared. The stereochemistry of the alpha-methylene-gamma-lactones was established by convergent synthesis of their reduction products from epoxides of known absolute stereochemistry. In general, the tested compounds showed comparable affinity and selectivity for the receptor subtypes. All were found with high affinity for mu-sites. The terminal epoxide ether diastereomers 8 and 9 were not bound irreversibly in the assay for total opioid receptors. The alpha-methylene-gamma-lactone diastereomers 10 and 11, and their O-14-acetyl precursors 20 and 21, respectively, varied in their irreversible effects, but where noted these effects were mu-site selective. Methacrylate ether 7 and isothiocyanate ether 12 were bound irreversibly at both mu- and delta-sites.

  DOI：

  10.1021/jm00091a005

文献信息

• Electrophilic opioid ligands. Oxygen-tethered .alpha.-methylene-.gamma.-lactone, acrylate, isothiocyanate, and epoxide derivatives of 6.beta.-naltrexol
  作者：William E. Dasher、Peter Klein、Wendel L. Nelson

  DOI：10.1021/jm00091a005

  日期：1992.6

  O6-Ether derivatives of 6-beta-naltrexol in which the ether substituent includes various electrophilic groups have been synthesized in an effort to examine structure-activity requirements at the 6-beta-substituent for receptor affinity and irreversibility of binding in opioid receptor preparations. A series of tethered 6-beta-ethers having terminal epoxides, alpha-methylene-gamma-lactones, and an isothiocyanate group were prepared. The stereochemistry of the alpha-methylene-gamma-lactones was established by convergent synthesis of their reduction products from epoxides of known absolute stereochemistry. In general, the tested compounds showed comparable affinity and selectivity for the receptor subtypes. All were found with high affinity for mu-sites. The terminal epoxide ether diastereomers 8 and 9 were not bound irreversibly in the assay for total opioid receptors. The alpha-methylene-gamma-lactone diastereomers 10 and 11, and their O-14-acetyl precursors 20 and 21, respectively, varied in their irreversible effects, but where noted these effects were mu-site selective. Methacrylate ether 7 and isothiocyanate ether 12 were bound irreversibly at both mu- and delta-sites.