3-O-Methylnaltrindole | 126580-44-7

• 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-O-Methylnaltrindole
• 英文别名: (5R,9R,13S,14S)-17-cyclopropylmethyl-6,7-didehydro-4,5-epoxy-3-methoxyindolo[2',3':6,7]morphinan-14-ol；(1S,2S,13R,21R)-22-(cyclopropylmethyl)-16-methoxy-14-oxa-11,22-diazaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5,7,9,15,17,19(25)-heptaen-2-ol
• CAS: 126580-44-7
• 化学式: C₂₇H₂₈N₂O₃
• 分子量: 428.531
• InChiKey: HKUIBYDTKWHKJU-NVSKSXHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  57.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-O-Methylnaltrindole 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以82%的产率得到17-环丙基甲基-6,7-去氢-4,5-环氧-3,14-二羟基-6,7,2',3'-吲哚并吗喃
  参考文献：
  名称：

  L-Selectride as a General Reagent for the O-Demethylation and N-Decarbomethoxylation of Opium Alkaloids and Derivatives¹

  摘要：

  L-Selectride was shown to be an efficient and general O-demethylating agent for the opium alkaloids and their derivatives and also an efficient reagent for the cleavage of methyl carbamates, thus offering a convenient method for the N-demethylation of opioids. Further, it was shown that by choice of reaction conditions it is possible to achieve both N-decarbomethoxylation and O-demethylation in one pot, or only render N-decarbomethoxylation in high yield without accompanying O-demethylation.

  DOI：

  10.1021/jo9801972
• 作为产物：
  描述：

  重氮甲烷 、 17-环丙基甲基-6,7-去氢-4,5-环氧-3,14-二羟基-6,7,2',3'-吲哚并吗喃 以 乙醚 为溶剂， 以86%的产率得到3-O-Methylnaltrindole
  参考文献：
  名称：

  Delta opioid binding selectivity of 3-ether analogs of naltrindole

  摘要：

  Masking of the 3-phenol of naltrindole as a range of ethers caused a decrease in binding affinity at all three opiate receptors (mu, kappa, delta), however for the methyl ether, the reduction in affinity at both mu and kappa was greater than at delta, thereby increasing delta binding selectivity. (C) 1999 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(99)00622-8

文献信息

• L-Selectride as a General Reagent for the O-Demethylation and N-Decarbomethoxylation of Opium Alkaloids and Derivatives¹
  作者：Andrew Coop、James W. Janetka、John W. Lewis、Kenner C. Rice

  DOI：10.1021/jo9801972

  日期：1998.6.1

  L-Selectride was shown to be an efficient and general O-demethylating agent for the opium alkaloids and their derivatives and also an efficient reagent for the cleavage of methyl carbamates, thus offering a convenient method for the N-demethylation of opioids. Further, it was shown that by choice of reaction conditions it is possible to achieve both N-decarbomethoxylation and O-demethylation in one pot, or only render N-decarbomethoxylation in high yield without accompanying O-demethylation.
• Delta opioid binding selectivity of 3-ether analogs of naltrindole
  作者：Andrew Coop、Julia Pinto、Lijuan Wang、Karen McCullough、Richard B. Rothman、Christine Dersch、Arthur E. Jacobson、Kenner C. Rice

  DOI：10.1016/s0960-894x(99)00622-8

  日期：1999.12

  Masking of the 3-phenol of naltrindole as a range of ethers caused a decrease in binding affinity at all three opiate receptors (mu, kappa, delta), however for the methyl ether, the reduction in affinity at both mu and kappa was greater than at delta, thereby increasing delta binding selectivity. (C) 1999 Published by Elsevier Science Ltd.