(4'R,4a'S,7a'R,12b'S,13'S)-10'-chloro-3'-(cyclopropylmethyl)-9'-methoxy-1',2',3',4',5',6'-hexahydro-4a'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinoline]-4a',13'-diol | 619331-83-8

• 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,4a'S,7a'R,12b'S,13'S)-10'-chloro-3'-(cyclopropylmethyl)-9'-methoxy-1',2',3',4',5',6'-hexahydro-4a'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinoline]-4a',13'-diol
• CAS: 619331-83-8
• 化学式: C₂₃H₂₈ClNO₆
• 分子量: 449.931
• InChiKey: ISBGAQVRZFHUCM-LOONRQLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  80.62
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (4'R,4a'S,7a'R,12b'S,13'S)-10'-chloro-3'-(cyclopropylmethyl)-9'-methoxy-1',2',3',4',5',6'-hexahydro-4a'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinoline]-4a',13'-diol 在 三溴化硼 作用下， 以 二氯甲烷 、 苯 为溶剂， 以70%的产率得到2-chloro-10α-hydroxynaltrexone
  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：

  (4'R,4a'S,7a'R,12b'S)-10'-chloro-3'-(cyclopropylmethyl)-4a'-hydroxy-2',3',4',4a',5',6'-hexahydro-1'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinolin]-9'-yl diethylcarbamate 在 chromium(VI) oxide 、 sodium periodate 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 硫酸 为溶剂， 生成 (4'R,4a'S,7a'R,12b'S,13'S)-10'-chloro-3'-(cyclopropylmethyl)-9'-methoxy-1',2',3',4',5',6'-hexahydro-4a'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinoline]-4a',13'-diol
  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