10-(tert-butyldimethylsilyl)-4-(trimethylsilyl)-3,5,6,7,8,9-hexahydro-2H-fluoreno[3,2-b]furan-5-yl acetate | 1411943-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 10-(tert-butyldimethylsilyl)-4-(trimethylsilyl)-3,5,6,7,8,9-hexahydro-2H-fluoreno[3,2-b]furan-5-yl acetate
• 英文别名: 11-(tert-butyldimethylsilyl)-4-(trimethylsilyl)-2,3,5,6,7,8,9,10-octahydrocyclohepta[2,3]-indeno[5,6-b]furan-5-yl acetate；[4-[tert-butyl(dimethyl)silyl]-10-trimethylsilyl-2,5,6,7,8,9-hexahydro-1H-indeno[2,3-f][1]benzofuran-9-yl] acetate
• CAS: 1411943-70-8
• 化学式: C₂₆H₄₀O₃Si₂
• 分子量: 456.773
• InChiKey: ITORBWJRNDUTOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 作用下， 以 氘代甲苯 为溶剂， 生成 10-(tert-butyldimethylsilyl)-4-(trimethylsilyl)-3,5,6,7,8,9-hexahydro-2H-fluoreno[3,2-b]furan-5-yl acetate
  参考文献：
  名称：

  Rates of Hexadehydro-Diels–Alder (HDDA) Cyclizations: Impact of the Linker Structure

  摘要：

  The rates of the hexadehydro-Diels-Alder (HDDA) reaction of substrates containing, minimally, a 1,3,8-triyne subunit are reported. Several series of related substrates, differing in the nature of the three-atom tether that links the 1,3-diyne and diynophile, were examined. Seemingly small changes in substrate structure result in large differences in cyclization rate, spanning more than 8 orders of magnitude. The reactivity trends revealed by these studies should prove useful in guiding substrate design and choice of reaction conditions in future applications.

  DOI：

  10.1021/ol502131r

文献信息

• The hexadehydro-Diels–Alder reaction
  作者：Thomas R. Hoye、Beeraiah Baire、Dawen Niu、Patrick H. Willoughby、Brian P. Woods

  DOI：10.1038/nature11518

  日期：2012.10.11

  produce the highly reactive benzyne intermediate. The reaction conditions for this simple, thermal transformation are notable for being free of metals and reagents. The subsequent and highly efficient trapping reactions increase the power of the overall process. Finally, we provide examples of how this de novo benzyne generation approach allows new modes of intrinsic reactivity to be revealed.

  芳炔（形式上包含碳-碳三键的芳香系统）是有机化学中所有反应性中间体中用途最广泛的。它们可以被“捕获”以产生用作药物、农用化学品、染料、聚合物和其他精细化学品的产品。在这里，我们探索了一种策略，该策略通过六氢-Diels-Alder 反应将苄的从头生成与它们原位加工成结构复杂的苯类产物相结合。在六氢-Diels-Alder 反应中，1,3-二炔与“亲二炔体”发生 [4+2] 环异构化反应，生成高反应性苯炔中间体。这种简单的热转化的反应条件以不含金属和试剂而著称。随后的高效捕集反应增加了整个过程的能力。
• CYCLIZATION METHODS
  申请人：MINNESOTA REGENTS OF THE UNIVERSITY OF

  公开号：US20130197241A1

  公开（公告）日：2013-08-01

  The invention provides methods for cyclizing poly-yne compounds under mild conditions to provide cyclic compounds.

  该发明提供了在温和条件下将聚炔化合物环化为环状化合物的方法。