exo-anti-endo-1,4,4a,5,8,8a,9a,10a-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione | 130855-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: exo-anti-endo-1,4,4a,5,8,8a,9a,10a-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione
• 英文别名: (1S,2S,4S,5R,8S,9R,11R,12R)-pentacyclo[10.2.1.15,8.02,11.04,9]hexadeca-6,13-diene-3,10-dione
• CAS: 130855-43-5
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: ZCJHLBHJGLCVRU-WBRCCVPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  exo-anti-endo-1,4,4a,5,8,8a,9a,10a-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione 生成 (1S,2S,4S,5R,9R,11R,12R)-pentacyclo[10.2.1.15,8.02,11.04,9]hexadecane-3,10-dione
  参考文献：
  名称：

  YATES, PETER;SWITLAK, KRZYSZTOF, CAN. J. CHEM., 68,(1990) N0, C. 1894-1900

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,2S,4S,5S,8R,9R,11R,12R)-pentacyclo[10.2.1.15,8.02,11.04,9]hexadeca-6,13-diene-3,10-dione 生成 exo-anti-endo-1,4,4a,5,8,8a,9a,10a-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione
  参考文献：
  名称：

  YATES, PETER;SWITLAK, KRZYSZTOF, CAN. J. CHEM., 68,(1990) N0, C. 1894-1900

  摘要：

  DOI：

文献信息

• Isomerization and functionalization of 2:1 Diels–Alder adducts of cyclopentadiene and p -benzoquinone: Applications to polycycles via ring-closing metathesis and ring-opening metathesis as key steps
  作者：Sambasivarao Kotha、Nalajala Nageswara Rao、Ongolu Ravikumar、Gaddamedi Sreevani

  DOI：10.1016/j.tetlet.2017.02.039

  日期：2017.3

  stereochemically different 2:1 Diels–Alder adducts were prepared starting with cyclopentadiene and p-benzoquinone. Separately, these adducts were treated with an excess amount of base and allyl bromide to deliver two different tetra-allylated products. These allyl derivatives gave the corresponding mono-propellane derivatives on metathesis sequence. Five Diels–Alder adducts on treatment with Grubbs ruthenium

  从环戊二烯和对苯醌开始，制备了五种立体化学不同的2：1 Diels-Alder加合物。分别地，这些加合物用过量的碱和烯丙基溴处理，以递送两种不同的四烯丙基化产物。这些烯丙基衍生物在复分解序列上给出了相应的单丙炔衍生物。用Grubbs钌催化剂处理的五种Diels-Alder加合物提供了相应的单环和双环易位产物。通过单晶X射线衍射研究确定了三种功能化加合物的结构。
• Diels–Alder reactions in confined spaces: the influence of catalyst structure and the nature of active sites for the retro-Diels–Alder reaction
  作者：Ángel Cantín、M Victoria Gomez、Antonio de la Hoz

  DOI：10.3762/bjoc.12.208

  日期：——

  Diels-Alder cycloaddition between cyclopentadiene and p-benzoquinone has been studied in the confined space of a pure silica zeolite Beta and the impact on reaction rate due to the concentration effect within the pore and diffusion limitations are discussed. Introduction of Lewis or Bronsted acid sites on the walls of the zeolite strongly increases the reaction rate. However, contrary to what occurs

  在纯硅沸石β的密闭空间内，研究了环戊二烯与对苯醌之间的狄尔斯-阿尔德环加成反应，并讨论了由于孔内浓度效应和扩散限制而对反应速率的影响。在沸石壁上引入路易斯酸或布朗斯台德酸位点强烈地提高了反应速率。但是，与介孔分子筛（MCM-41）发生的情况相反，β沸石不能催化Diels-Alder逆反应，因此对环加成反应具有高度选择性。
• Studies of Diastereoselectivity in Diels−Alder Reactions of (S)<i>S</i>-4a,5,8,8a-Tetrahydro-5,8-methane-2-(<i>p</i>-tolylsulfinyl)-1,4-naphtho- quinones with Cyclopentadiene
  作者：M. Carmen Carreño、José L. García Ruano、Antonio Urbano、Miguel A. Hoyos

  DOI：10.1021/jo9521209

  日期：1996.1.1

  compounds 6 and 7 have proved to be adequate rigid models to evaluate the ability of the sulfinyl group to control the diastereoselectivity of the [4 + 2] cycloadditions of cyclopentadiene on the ene-dione moiety. The results of thermal and Lewis acid-catalyzed reactions allowed us to establish that both reactivity and endo/exo selectivity were modulated by the presence of the sulfinyl group, the endo-anti-endo

  标题化合物6和7已被证明是适当的刚性模型，可用于评估亚磺酰基控制在烯二酮部分上环戊二烯的[4 + 2]环加成的非对映选择性。热和路易斯酸催化反应的结果使我们能够确定，亚砜基的存在可调节反应性和内/外选择性，内-反-内或外-反-内双加合物是主要的产品取决于实验条件。使用了SOTol基团与几种路易斯酸（BF（3）.OEt（2），Eu（fod）（3），ZnBr（2））之间的缔合作用，该位移移位了CS键周围的构象平衡解释主要受空间因素控制的环加成反应的立体化学过程。
• Yates, Peter; Switlak, Krzysztof, Canadian Journal of Chemistry, 1990, vol. 68, # 10, p. 1894 - 1900
  作者：Yates, Peter、Switlak, Krzysztof

  DOI：——

  日期：——
• Cyclopentadiene bisadduct of tetrafluoro-p-benzoquinone: its stereochemistry, reactivity toward nucleophiles, and photochemistry
  作者：R. Marshall Wilson

  DOI：10.1021/jo00153a017

  日期：1983.3