2-(2-(2λ⁵-propa-1,2-dien-1-yl)cyclohexylidene)malononitrile | 64686-48-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(2-(2λ⁵-propa-1,2-dien-1-yl)cyclohexylidene)malononitrile
• CAS: 64686-48-2
• 化学式: C₁₂H₁₂N₂
• 分子量: 184.241
• InChiKey: UEQUYEQQHKDQDA-UHFFFAOYSA-N

物化性质

• 沸点：
  331.3±32.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-(2λ⁵-propa-1,2-dien-1-yl)cyclohexylidene)malononitrile 生成 5,6,7,8-tetrahydronaphthalene-1,3-dicarbonitrile
  参考文献：
  名称：

  Brown,R.F.C.; McAllan,C.G., Australian Journal of Chemistry, 1977, vol. 30, p. 1747 - 1755

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(cyclohex-1-en-1-yl)-2-(prop-2-yn-1-yl)malononitrile 以 甲苯 为溶剂， 反应 15.0h， 以85%的产率得到2-(2-(2λ⁵-propa-1,2-dien-1-yl)cyclohexylidene)malononitrile
  参考文献：
  名称：

  Enyne Cope重排使得能够从容易获得的起始原料合成聚环烷烃

  摘要：

  环己酮衍生的Knoevenagel加合物（环己叉基丙二腈）和两种不同的炔丙基亲电试剂可作为碳源来组装各种6/7/5三环烷烃（一种常见的萜烯骨架）。该序列涉及三个独特的反应：1）去共轭炔丙基化； 2）单罐烯炔应对反应重排/去共轭炔丙基化； 3）烯丙基Pauson-Khand反应。

  DOI：

  10.1002/anie.201703186

文献信息

• Controlling, Understanding, and Redirecting the Thermal Rearrangement of 3,3-Dicyano-1,5-enynes
  作者：Sarah K. Scott、Jacob N. Sanders、Katherine E. White、Roland A. Yu、K. N. Houk、Alexander J. Grenning

  DOI：10.1021/jacs.8b08553

  日期：2018.11.28

  The thermal [3,3] rearrangement of 3,3-dicyano-1,5-enynes to γ-allenyl alkylidenemalononitriles (the "enyne Cope rearrangement") has largely eluded synthetic value as the desired products, too, are thermally reactive and ultimately yield 6π electrocyclization products. Herein, we describe experimental and computational studies related to the thermal rearrangement of 1,5-enynes, structural features

  3,3-二氰基-1,5-烯炔的热[3,3]重排生成γ-丙二烯基亚烷基丙二腈（“烯炔Cope重排”）在很大程度上回避了合成价值，因为所需的产物也具有热反应性并最终产生6π电环化产物。在此，我们描述了与 1,5-烯炔热重排相关的实验和计算研究、在丙二烯阶段停止热重排的结构特征以及用于制备双功能联烯基丙二腈的还原变体。我们还描述了操纵双功能构建块并将其转换为循环和非循环架构的各种方法。
• Methods and compositions for terpenoid tricycloalkane synthesis
  申请人：University of Florida Research Foundation, Inc.

  公开号：US10287239B1

  公开（公告）日：2019-05-14

  In one aspect, the disclosure relates to methods for preparation of intermediates useful for the preparation of terpenoid cores. In a further aspect, the disclosed methods pertain to the preparation of compounds comprising a terpenoid core or scaffold, such as 6/7/5 tricycloalkanes. The disclosed methods utilize abundant starting materials and simple reaction sequences that can be used to tunably and scalably assemble common terpenoid cores. In various aspects, the present disclosure pertains to compounds prepared using the disclosed methods. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.

  在一个方面，本公开涉及用于制备对萜类核心的制备有用的中间体的方法。在另一个方面，所公开的方法涉及制备包括萜类核心或支架的化合物，例如6/7/5三环脂环烷。所公开的方法利用丰富的起始材料和简单的反应序列，可用于可调和可扩展地组装常见的萜类核心。在各个方面，本公开涉及使用所公开方法制备的化合物。本摘要旨在作为搜索特定领域的扫描工具，并不意味着对本公开的限制。
• METHODS AND COMPOSITIONS FOR TERPENOID TRICYCLOALKANE SYNTHESIS
  申请人：University of Florida Research Foundation, Inc.

  公开号：US20190352254A1

  公开（公告）日：2019-11-21

  In one aspect, the disclosure relates to methods for preparation of intermediates useful for the preparation of terpenoid cores. In a further aspect, the disclosed methods pertain to the preparation of compounds comprising a terpenoid core or scaffold, such as 6/7/5 tricycloalkanes. The disclosed methods utilize abundant starting materials and simple reaction sequences that can be used to tunably and scalably assemble common terpenoid cores. In various aspects, the present disclosure pertains to compounds prepared using the disclosed methods. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.