(R)-2-[6,7-dimethoxy-2-(4-methylpentanoyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]acetaldehyde | 1228458-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (R)-2-[6,7-dimethoxy-2-(4-methylpentanoyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]acetaldehyde
• 英文别名: 2-[(1R)-6,7-dimethoxy-2-(4-methylpentanoyl)-3,4-dihydro-1H-isoquinolin-1-yl]acetaldehyde
• CAS: 1228458-08-9
• 化学式: C₁₉H₂₇NO₄
• 分子量: 333.428
• InChiKey: RGHBQPNGROMJMM-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-[6,7-dimethoxy-2-(4-methylpentanoyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]acetaldehyde 在 异丙基氯化镁 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (5S,6R,E)-6-((tert-butyldimethylsilyl)oxy)-5-isobutyl-10,11-dimethoxy-2,3,5,6-tetrahydrobenzo[d]azecin-4(1H)-one
  参考文献：
  名称：

  PROCESS FOR MAKING A PHARMACEUTICAL COMPOUND

  摘要：

  This invention relates to a novel process for making dihydrotetrabenazines, and in particular (+)-α-dihydrotetrabenazine, novel synthetic intermediates for use in the process and processes for making the intermediates.

  公开号：

  US20230331667A1
• 作为产物：
  描述：

  (1-allyl-6,7-dimethoxy-3, 4-dihydroisoquinolin-2(1H)-yl)-4-methylpentan-1-one 在 四氧化锇 、 N-甲基吗啉氧化物 、 sodium periodate 作用下， 以 水 、 丙酮 、 二氯甲烷 为溶剂， 生成 (R)-2-[6,7-dimethoxy-2-(4-methylpentanoyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]acetaldehyde
  参考文献：
  名称：

  PROCESS FOR MAKING A PHARMACEUTICAL COMPOUND

  摘要：

  This invention relates to a novel process for making dihydrotetrabenazines, and in particular (+)-α-dihydrotetrabenazine, novel synthetic intermediates for use in the process and processes for making the intermediates.

  公开号：

  US20230331667A1

文献信息

• A Concise Total Synthesis of (+)-Tetrabenazine and (+)-α-Dihydrotetrabenazine
  作者：Seung-Mann Paek、Nam-Jung Kim、Dongyun Shin、Jae-Kyung Jung、Jong-Wha Jung、Dong-Jo Chang、Hyunyoung Moon、Young-Ger Suh

  DOI：10.1002/chem.200902591

  日期：2010.4.19

  AbstractHighly concise asymmetric total syntheses of (+)‐tetrabenazine (1), a drug for the treatment of chorea associated with Huntington’s disease, and of (+)‐α‐dihydrotetrabenazine (2), an active metabolite of 1, have been accomplished. Our synthetic route features a trans‐selective enol etherification, followed by an unprecedented cation‐dependent aza‐Claisen rearrangement to establish the carbon framework and two stereogenic centers of tetrabenazine. The syntheses consist of seven steps (34 % overall yield) for (+)‐2 and eight steps (22 % overall yield) for (+)‐1.
• PROCESS FOR MAKING A PHARMACEUTICAL COMPOUND
  申请人：Adeptio Pharmaceuticals Limited

  公开号：US20230331667A1

  公开（公告）日：2023-10-19

  This invention relates to a novel process for making dihydrotetrabenazines, and in particular (+)-α-dihydrotetrabenazine, novel synthetic intermediates for use in the process and processes for making the intermediates.