8-(tert-butyldimethylsilyl)-4-(5-((tert-butyldimethylsilyl)oxy)pent-1-yn-1-yl)-5,6-dihydro-2H-indeno[5,6-b]furan-7(3H)-one | 1448613-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 8-(tert-butyldimethylsilyl)-4-(5-((tert-butyldimethylsilyl)oxy)pent-1-yn-1-yl)-5,6-dihydro-2H-indeno[5,6-b]furan-7(3H)-one
• 英文别名: 8-(tert-butyldimethylsilyl)-4-(5-((tert-butyldimethylsilyl)oxy)pent-1-yn-1-yl)-2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-one；8-[Tert-butyl(dimethyl)silyl]-4-[5-[tert-butyl(dimethyl)silyl]oxypent-1-ynyl]-2,3,5,6-tetrahydrocyclopenta[f][1]benzofuran-7-one；8-[tert-butyl(dimethyl)silyl]-4-[5-[tert-butyl(dimethyl)silyl]oxypent-1-ynyl]-2,3,5,6-tetrahydrocyclopenta[f][1]benzofuran-7-one
• CAS: 1448613-60-2
• 化学式: C₂₈H₄₄O₃Si₂
• 分子量: 484.827
• InChiKey: ISGUUOAMAYFDDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  ((5-bromopent-4-yn-1-yl)oxy)(tert-butyl)dimethylsilane 在 哌啶 、 manganese(IV) oxide 、 pyridinium chlorochromate 、 copper(l) chloride 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 43.5h， 生成 9-(tert-butyldimethylsilyl)-5-(4-((tert-butyldimethylsilyl)oxy)but-1-yn-1-yl)-3,4,7,8-tetrahydrocyclopenta[g]chromen-6(2H)-one 、 8-(tert-butyldimethylsilyl)-4-(5-((tert-butyldimethylsilyl)oxy)pent-1-yn-1-yl)-5,6-dihydro-2H-indeno[5,6-b]furan-7(3H)-one
  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

• 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。
• Rates of Hexadehydro-Diels–Alder (HDDA) Cyclizations: Impact of the Linker Structure
  作者：Brian P. Woods、Beeraiah Baire、Thomas R. Hoye

  DOI：10.1021/ol502131r

  日期：2014.9.5

  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.