ethyl (4Z)-2-(prop-2-ynyl)hept-4-enoate | 656234-74-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (4Z)-2-(prop-2-ynyl)hept-4-enoate
• 英文别名: ethyl (Z)-2-(prop-2-ynyl)hept-4-enoate；ethyl (Z)-2-prop-2-ynylhept-4-enoate
• CAS: 656234-74-1
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: PBBLASASBMBSSA-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (4Z)-2-(prop-2-ynyl)hept-4-enoate 在 Grubbs catalyst first generation 咪唑 、 lithium aluminium tetrahydride 、 碘 、 双(三甲基硅烷基)氨基钾 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.5h， 生成 (1R,3S,6R,7R,10R,11S,13E)-7-[(2S)-1-[tert-butyl(dimethyl)silyl]oxypropan-2-yl]-6-methyltetracyclo[12.3.1.03,11.06,10]octadeca-13,15-dien-11-ol
  参考文献：
  名称：

  Tandem RCM of Dienynes for the Construction of Taxol-Type Carbocyclic Systems

  摘要：

  [GRAPHICS]Tandem ring-closing metathesis of hydrindanone dienynes allows access to taxosteroids, a new class of compounds that combine the [5.3.1] carbocyclic system of taxanes with rings C and D of the steroid skeleton.

  DOI：

  10.1021/ol036062m
• 作为产物：
  描述：

  1-bromopent-2-ene 在 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 52.5h， 生成 ethyl (4Z)-2-(prop-2-ynyl)hept-4-enoate
  参考文献：
  名称：

  Tandem RCM of Dienynes for the Construction of Taxol-Type Carbocyclic Systems

  摘要：

  [GRAPHICS]Tandem ring-closing metathesis of hydrindanone dienynes allows access to taxosteroids, a new class of compounds that combine the [5.3.1] carbocyclic system of taxanes with rings C and D of the steroid skeleton.

  DOI：

  10.1021/ol036062m

文献信息

• Dienyne Ring-Closing Metathesis Approach for the Construction of Taxosteroids
  作者：María J. Aldegunde、Rebeca García-Fandiño、Luis Castedo、Juan R. Granja

  DOI：10.1002/chem.200601685

  日期：2007.6.15

  hybrid compounds-the taxosteroids-possessing carbon frameworks incorporating moieties characteristic of both taxanes (such as AB rings) and steroids (i.e., CD system and side chain). This tandem cyclization is highly stereoselective, allowing the one-step formation of the bicyclo[5.3.1]undecene system characteristic of taxol. In this work we describe the scope and limitations of such cyclizations.

  级联二烯炔闭环复分解方法已用于合成一类新的杂化化合物的四环碳构架-紫杉类固醇-具有并入了紫杉烷类化合物（例如AB环）和类固醇（即CD系统和侧链）。这种串联环化是高度立体选择性的，允许一步形成紫杉醇的双环[5.3.1]十一碳烯系统。在这项工作中，我们描述了这种环化的范围和局限性。
• METHOD OF OBTAINING TAXOSTEROIDS AND PRECURSORS THEREOF
  申请人：UNIVERSIDADE DE SANTIAGO DE COMPOSTELA

  公开号：EP1642902A2

  公开（公告）日：2006-04-05

  The present invention relates to a process of obtaining taxosteroids and precursors thereof from the hydrindane bicyclic ring system. The compounds have a tetracyclic system which combines the structural characteristics of taxanes, such as the bicyclo[5.3.1]undecane system (cycles A and B), fused to a six-membered ring (C), and of steroids, such as the CD bicycle, the A ring and the side chain (Sc). The process of preparing the compounds and their application as compositions with pharmacological properties of interest are described.

  本发明涉及一种从水合马来烷双环环系统中获取紫杉醇类化合物及其前体的方法。这些化合物具有四环系统，结构特征包括紫杉醇的自行车[5.3.1]十一烷环系统（环A和B）与一个六元环（C）融合，以及类固醇的CD自行车、A环和侧链（Sc）。描述了制备这些化合物及其应用作具有药理学性质的组合物的方法。
• PROCESS OF OBTAINING TAXOSTEROIDS AND PRECURSORS THEREOF
  申请人：Granja Guillan Juan

  公开号：US20070185108A1

  公开（公告）日：2007-08-09

  The present invention relates to a process of obtaining taxosteroids and precursors thereof from the hydrindane bicyclic ring system. The compounds have a tetracyclic system which combines the structural characteristics of taxanes, such as the bicyclo[5.3.1]undecane system (cycles A and B), fused to a six-membered ring (C), and of steroids, such as the CD bicycle, the A ring and the side chain (Sc). The process of preparing the compounds and their application as compositions with pharmacological properties of interest are described.
• US7618999B2
  申请人：——

  公开号：US7618999B2

  公开（公告）日：2009-11-17