5-Methylhomophthalic anhydride | 84944-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-Methylhomophthalic anhydride
• 英文别名: 5-Methylisochroman-1,3-dione；5-methyl-4H-isochromene-1,3-dione
• CAS: 84944-47-8
• 化学式: C₁₀H₈O₃
• 分子量: 176.172
• InChiKey: WLNCTDMMBYZQDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Methylhomophthalic anhydride 在 4-二甲氨基吡啶 吡啶 、 氢氧化钾 、 PPA 、 四甲基乙二胺 、 叔丁基锂 、 仲丁基锂 、 对甲苯磺酸 、 锌 作用下， 以 甲醇 、 溶剂黄146 、 苯 为溶剂， 反应 61.0h， 生成 3-甲基胆蒽
  参考文献：
  名称：

  A highly efficient synthesis of 3-methylcholanthrene

  摘要：

  A five-step synthesis of 3-methylcholanthrene (1) has been achieved starting from 5-methylhomophthalic anhydride and N,N-diethyl-1-naphthamide in 55% over all yield. Treatment of a solution of the preformed lithium enolate of 5-methylhomophthalic anhydride (3) with an equimolar solution of 2-lithio-1-naphthamide (4), followed by acid hydrolysis, provides cleanly the spirobislactone 5 in 80% overall yield. In addition, the synthesis features a unique, highly selective double Friedel-Crafts cyclization of the aryl diacid 2 with PPA to give rise, after acetylation, to keto acetate 6.

  DOI：

  10.1021/jo00077a045
• 作为产物：
  描述：

  3-methylhomophthalic acid 以 甲苯 为溶剂， 生成 5-Methylhomophthalic anhydride
  参考文献：
  名称：

  1H-苯并[4,5]恶唑并吡啶酮的区域选择性和天基选择性开环

  摘要：

  N-芳基异喹啉-1,3(2 H ,4 H )-二酮的空间选择性合成实现了区域选择性和立体选择性 C−O 活化。该方法通过对映选择性开环动态动力学拆分过程，建立了 C−N 阻转异构体合成的新合成策略。

  DOI：

  10.1002/anie.202402231

文献信息

• NOVEL INHIBITORS OF FLAVIVIRUS REPLICATION
  申请人：Bardiot Dorothée

  公开号：US20110224208A1

  公开（公告）日：2011-09-15

  The present invention relates to a series of Isoquinolone derivatives which are suitable to treat infections with viruses belonging to the family of the Flaviviridae and more preferably infections with Hepatitis C virus (HCV). The present invention also relates to Isoquinolone compounds for use as a medicine for the prevention or treatment of viral infections, preferably infections with viruses belonging to the family of the Flaviviridae.

  本发明涉及一系列异喹啉衍生物，适用于治疗属于黄病毒科家族的病毒感染，更优选地是治疗丙型肝炎病毒（HCV）感染。本发明还涉及异喹啉化合物作为预防或治疗病毒感染的药物，优选是治疗属于黄病毒科家族的病毒感染。
• Stereopopulation control. VIII. Rate and equilibrium enhancement in the formation of homophthalic anhydrides
  作者：Paul S. Hillery、Louis A. Cohen

  DOI：10.1021/ja00347a041

  日期：1983.5
• ISOQUINOLONE DERIVATIVES AS INHIBITORS OF PLAVIVIRUS REPLICATION
  申请人：Katholieke Universiteit Leuven, K.U. Leuven R&D

  公开号：EP2358682A2

  公开（公告）日：2011-08-24
• [EN] NOVEL INHIBITORS OF FLAVIVIRUS REPLICATION<br/>[FR] NOUVEAUX INHIBITEURS DE LA RÉPLICATION DE FLAVIVIRUS
  申请人：UNIV LEUVEN KATH

  公开号：WO2010055164A2

  公开（公告）日：2010-05-20

  The present invention relates to a series of Isoquinolone derivatives which are suitable to treat infections with viruses belonging to the family of the Flaviviridae and more preferably infections with Hepatitis C virus (HCV). The present invention also relates to Isoquinolone compounds for use as a medicine for the prevention or treatment of viral infections, preferably infections with viruses belonging to the family of the Flaviviridae.
• A highly efficient synthesis of 3-methylcholanthrene
  作者：Thanasis Gimisis、Masato Koreeda

  DOI：10.1021/jo00077a045

  日期：1993.12

  A five-step synthesis of 3-methylcholanthrene (1) has been achieved starting from 5-methylhomophthalic anhydride and N,N-diethyl-1-naphthamide in 55% over all yield. Treatment of a solution of the preformed lithium enolate of 5-methylhomophthalic anhydride (3) with an equimolar solution of 2-lithio-1-naphthamide (4), followed by acid hydrolysis, provides cleanly the spirobislactone 5 in 80% overall yield. In addition, the synthesis features a unique, highly selective double Friedel-Crafts cyclization of the aryl diacid 2 with PPA to give rise, after acetylation, to keto acetate 6.