[(4'R,4'aS,7'aR,12'bS)-3'-(cyclopropylmethyl)-4'a-hydroxyspiro[1,3-dioxolane-2,7'-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline]-9'-yl] N,N-diethylcarbamate | 619331-80-5

• 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: [(4'R,4'aS,7'aR,12'bS)-3'-(cyclopropylmethyl)-4'a-hydroxyspiro[1,3-dioxolane-2,7'-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline]-9'-yl] N,N-diethylcarbamate
• CAS: 619331-80-5
• 化学式: C₂₇H₃₆N₂O₆
• 分子量: 484.593
• InChiKey: YZAGASYRNZKJQB-AAVWJAMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(4'R,4'aS,7'aR,12'bS)-3'-(cyclopropylmethyl)-4'a-hydroxyspiro[1,3-dioxolane-2,7'-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline]-9'-yl] N,N-diethylcarbamate 在 chromium(VI) oxide 、 sodium periodate 、 lithium aluminium tetrahydride 、 四甲基乙二胺 、 六氯乙烷 、 仲丁基锂 作用下， 以 四氢呋喃 、 硫酸 为溶剂， 生成 (4'S,4a'S,7a'R,12b'S)-10'-chloro-3'-(cyclopropylmethyl)-4a'-hydroxy-9'-methoxy-2',3',4',4a',5',6'-hexahydro-1'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinolin]-13'-one
  参考文献：
  名称：

  Isolation and synthesis of 2-chloro-10-α-hydroxynaltrexone, a new naltrexone degradant

  摘要：

  The putative structure of a new degradant from REVIA((R)) tablets was assigned 2-chloro-10-alpha-hydroxynaltrexone 2. A route for the independent synthesis was developed wherein a N,N-diethylcarbamate derivative directed an ortho-metallation of the naltrexone nucleus, leading to the desired 2-chloro functionality. Oxidation of the 10-position, followed by deprotection provided 2, which was identical in all respects to the original isolate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01797-0
• 作为产物：
  描述：

  盐酸纳曲酮 在 吡啶 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 [(4'R,4'aS,7'aR,12'bS)-3'-(cyclopropylmethyl)-4'a-hydroxyspiro[1,3-dioxolane-2,7'-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline]-9'-yl] N,N-diethylcarbamate
  参考文献：
  名称：

  Isolation and synthesis of 2-chloro-10-α-hydroxynaltrexone, a new naltrexone degradant

  摘要：

  The putative structure of a new degradant from REVIA((R)) tablets was assigned 2-chloro-10-alpha-hydroxynaltrexone 2. A route for the independent synthesis was developed wherein a N,N-diethylcarbamate derivative directed an ortho-metallation of the naltrexone nucleus, leading to the desired 2-chloro functionality. Oxidation of the 10-position, followed by deprotection provided 2, which was identical in all respects to the original isolate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01797-0

文献信息

• [EN] HYDROXY-(R),(R)-2,2'-BISMETHYLNALTREXONES AND USES THEREOF<br/>[FR] HYDROXY-(R)-2,2'-BISMÉTHYLNALTREXONES ET LEURS UTILISATIONS
  申请人：SALIX PHARMACEUTICALS INC

  公开号：WO2016014864A8

  公开（公告）日：2016-03-24
• [EN] HYDROXY-(R)-2,2'-BISMETHYLNAL TREXONES AND USES THEREOF<br/>[FR] HYDROXY-(R)-2,2'-BISMÉTHYLNALTREXONES ET LEURS UTILISATIONS
  申请人：SALIX PHARMACEUTICALS INC

  公开号：WO2016014864A1

  公开（公告）日：2016-01-28

  The present application relates to compounds of Formula (I): wherein R1 and X are as defined herein, as well as methods for synthesis and use thereof. The present application also relates to 10'-hydroxy-(R),(R)-2,2'-bismethylnaltrexone, as well as methods for synthesis and use thereof.