[6]dendralene | 71413-62-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: [6]dendralene
• 英文别名: 3,4,5,6-Tetramethylideneocta-1,7-diene
• CAS: 71413-62-2
• 化学式: C₁₂H₁₄
• 分子量: 158.243
• InChiKey: RBABOPLFRQKABD-UHFFFAOYSA-N

物化性质

• 沸点：
  243.3±7.0 °C(Predicted)
• 密度：
  0.805±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  [6]dendralene 在 (5S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one trifluoromethanesulfonic acid salt 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 23.0h， 生成 [(1R)-4-[3-[(4R)-4-(hydroxymethyl)cyclohexen-1-yl]buta-1,3-dien-2-yl]cyclohex-3-en-1-yl]methanol
  参考文献：
  名称：

  Dendralenes的Domino环加成有机化学

  摘要：

  万岁！首次公开了高度对映选择性的有机催化Diels-Alder反应级联反应。该反应使得能够从简单的非手性，无环多烯高效且快速地构建对映纯多环。

  DOI：

  10.1002/anie.201302185
• 作为产物：
  描述：

  2-chloro[3]dendralene 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 magnesium 、 1,2-二溴乙烷 、 zinc dibromide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 [6]dendralene
  参考文献：
  名称：

  Discovery and Computational Rationalization of Diminishing Alternation in [n]Dendralenes

  摘要：

  The [n]dendralenes are a family of acyclic hydrocarbons which, by virtue of their ability to rapidly generate structural complexity, have attracted significant recent synthetic attention. [3]Dendralene through [8]dendralene have been previously prepared but no higher member of the family has been reported to date. Here, we describe the first chemical syntheses of the higher dendralenes, [9]dendralene through [12]dendralene. We also report a detailed investigation into the spectroscopic properties and chemical reactivity of the complete family of fundamental hydrocarbons, [3]dendralene to [12]dendralene. These studies reveal the first case of diminishing alternation in behavior in a series of related structures. We also report a comprehensive series of computational studies, which trace this dampening oscillatory effect in both spectroscopic measurements and chemical reactivity to conformational preferences.

  DOI：

  10.1021/jacs.5b11889

文献信息

• First Synthesis of the Dendralene Family of Fundamental Hydrocarbons
  作者：Simon Fielder、Daryl D. Rowan、Michael S. Sherburn

  DOI：10.1002/1521-3773(20001201)39:23<4331::aid-anie4331>3.0.co;2-3

  日期：2000.12.1
• Payne, Alan D.; Bojase, Gomotsang; Paddon-Row, Michael N., Angewandte Chemie - International Edition, 2009, vol. 48, p. 4836 - 4839
  作者：Payne, Alan D.、Bojase, Gomotsang、Paddon-Row, Michael N.、Sherburn, Michael S.

  DOI：——

  日期：——
• Nitroso-Dienophile Additions to Dendralenes: A Short Synthesis of Branched Aminosugars
  作者：Ruomeng Wang、Gomotsang Bojase、Anthony C. Willis、Michael N. Paddon-Row、Michael S. Sherburn

  DOI：10.1021/ol302619r

  日期：2012.11.16

  The first heteroatom-based dienophile cycloadditions to cross-conjugated alkenes ([n]dendralenes) are reported. Nitroso-dienophiles undergo smooth single and double Diels-Alder additions to the parent dendralenes with orientational regio- and stereoselectivity and, notably, with reactivity that depends upon the parity of the [n]dendralene. The first crystal structure of a cross-conjugated hexaene is reported. Vasella's nitroso-sugar reagent gives a highly enantiomerically enriched double cycloadduct with [3]dendralene. This bicyclic oxazine is successively dihydroxylated and then ring-opened to form a branched chain diamino tetrol.