(4bR,7S,9aS,10R)-7-hydroxy-1-methyl-8-methylene-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylate | 34707-34-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (4bR,7S,9aS,10R)-7-hydroxy-1-methyl-8-methylene-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylate
• 英文别名: epi-allogibberic methyl ester；Epiallogibberinsaeure-methylester；Methyl-(+)-epiallogibberat；methyl (1S,2R,9R,12S)-12-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.01,9.03,8]pentadeca-3,5,7-triene-2-carboxylate
• CAS: 34707-34-1
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: KAGDUESCODOTHQ-FXECBMLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  9-epiallogibberic acid 生成 (4bR,7S,9aS,10R)-7-hydroxy-1-methyl-8-methylene-4b,6,7,8,9,10-hexahydro-5H-7,9a-methanobenzo[a]azulene-10-carboxylate
  参考文献：
  名称：

  DRUGANOV, A. G.;PANKRUSHINA, N. A., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 257-258

  摘要：

  DOI：

文献信息

• Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations
  作者：Riley L. Svec、Paul J. Hergenrother

  DOI：10.1002/anie.201911896

  日期：2020.1.27

  Diazomethane is one of the most versatile reagents in organic synthesis, but its utility is limited by its hazardous nature. Although alternative methods exist to perform the unique chemistry of diazomethane, these suffer from diminished reactivity and/or correspondingly harsher conditions. Herein, we describe the repurposing of imidazotetrazines (such as temozolomide, TMZ, the standard of care for

  重氮甲烷是有机合成中用途最广泛的试剂之一，但其用途受到其危险性的限制。尽管存在执行重氮甲烷独特化学反应的替代方法，但这些方法会降低反应性和/或相应地更苛刻的条件。在此，我们描述了咪唑四嗪（例如替莫唑胺，TMZ，胶质母细胞瘤的护理标准）的再利用，用作烷基重氮试剂的合成前体。TMZ 被用于进行酯化和金属催化的环丙烷化反应，结果表明从各种底物形成甲酯特别有效且操作简单。TMZ 是一种市售固体，无爆炸性和无毒，应广泛用作重氮甲烷的替代品。
• Synthesis of substances related to Gibberellins—XXIV
  作者：K. Mori

  DOI：10.1016/s0040-4020(01)98196-7

  日期：1971.1

  A total synthesis of the title compound was accomplished employing a novel skeletal rearrangement.

  采用新颖的骨架重排完成了标题化合物的全合成。
• [EN] EXPEDITIOUS SYNTHESIS OF GIBBERLLIN A5 AND ESTERS THEREOF<br/>[FR] SYNTHESE RAPIDE DE GIBBERELLINE A5 ET DE SES ESTERS
  申请人：UNIV TECHNOLOGIES INTERNAT

  公开号：WO2010032136A1

  公开（公告）日：2010-03-25

  An expeditious synthesis of gibberellin A5 (GA5) esters is presented, from which GA5 may be prepared. The synthesis offers an inexpensive route of few steps to these compounds, starting from gibberellin A3 (GA3) esters in the presence of a metal hydride.

  本文介绍了一种快速合成赤霉素A5（GA5）酯的方法，从中可以制备GA5。该合成方法从赤霉素A3（GA3）酯开始，在金属氢化物的存在下，提供了一条简单、廉价的途径来制备这些化合物。
• EXPEDITIOUS SYNTHESIS OF GIBBERLLIN A5 AND ESTERS THEREOF
  申请人：Fairweather Kelly A.

  公开号：US20110263876A1

  公开（公告）日：2011-10-27

  An expeditious synthesis of gibberellin A 5 (GA 5 ) esters is presented, from which GA 5 may be prepared. The synthesis offers an inexpensive route of few steps to these compounds, starting from gibberellin A 3 (GA 3 ) esters in the presence of a metal hydride.
• US8461357B2
  申请人：——

  公开号：US8461357B2

  公开（公告）日：2013-06-11