[8]dendralene | 71413-60-0

• 分子结构分类: 有机化合物
• 英文名称: [8]dendralene
• 英文别名: 3,4,5,6,7,8-Hexamethylidenedeca-1,9-diene
• CAS: 71413-60-0
• 化学式: C₁₆H₁₈
• 分子量: 210.319
• InChiKey: YWPORNAHEZCVCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  330.6±9.0 °C(Predicted)
• 密度：
  0.833±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  16
• 可旋转键数：
  7
• 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：

  [8]dendralene 、 亚硝基苯 反应 20.0h， 以54%的产率得到4-[3,4-Dimethylidene-5-(2-phenyl-3,6-dihydrooxazin-4-yl)hexa-1,5-dien-2-yl]-2-phenyl-3,6-dihydrooxazine
  参考文献：
  名称：

  Nitroso-Dienophile Additions to Dendralenes: A Short Synthesis of Branched Aminosugars

  摘要：

  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.

  DOI：

  10.1021/ol302619r
• 作为产物：
  描述：

  2-chloro[3]dendralene 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 四(三苯基膦)钯 、 magnesium 、 1,2-二溴乙烷 、 potassium hydroxide 、 zinc dibromide 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 生成 [8]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

• Domino Cycloaddition Organocascades of Dendralenes
  作者：Nicholas J. Green、Andrew L. Lawrence、Gomotsang Bojase、Anthony C. Willis、Michael N. Paddon-Row、Michael S. Sherburn

  DOI：10.1002/anie.201302185

  日期：2013.8.5

  Hooray Horeau! Highly enantioselective organocatalyzed Diels–Alder reaction cascades are disclosed for the first time. The reaction enables the efficient and rapid construction of enantiopure polycycles from simple achiral, acyclic polyenes.

  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。
• 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：——