[7]dendralene | 71413-61-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: [7]dendralene
• 英文别名: 3,4,5,6,7-Pentamethylidenenona-1,8-diene；3,4,5,6,7-pentamethylidenenona-1,8-diene
• CAS: 71413-61-1
• 化学式: C₁₄H₁₆
• 分子量: 184.281
• InChiKey: ZIBYAXDRKFGSBF-UHFFFAOYSA-N

物化性质

• 沸点：
  288.7±7.0 °C(Predicted)
• 密度：
  0.821±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  14
• 可旋转键数：
  6
• 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：

  N-甲基马来酰亚胺 、 [7]dendralene 以 氘代氯仿 为溶剂， 反应 24.0h， 以73%的产率得到
  参考文献：
  名称：

  Payne, Alan D.; Bojase, Gomotsang; Paddon-Row, Michael N., Angewandte Chemie - International Edition, 2009, vol. 48, p. 4836 - 4839

  摘要：

  DOI：
• 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 [7]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

• 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.
• Discovery and Computational Rationalization of Diminishing Alternation in [<i>n</i>]Dendralenes
  作者：Mehmet F. Saglam、Thomas Fallon、Michael N. Paddon-Row、Michael S. Sherburn

  DOI：10.1021/jacs.5b11889

  日期：2016.1.27

  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.
• 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：——