(E)-1,10-dibenzyl dec-5-enedioate | 1332636-67-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1,10-dibenzyl dec-5-enedioate
• 英文别名: dibenzyl (E)-dec-5-enedioate
• CAS: 1332636-67-5
• 化学式: C₂₄H₂₈O₄
• 分子量: 380.484
• InChiKey: BURZYMFAWFFMFP-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1,10-dibenzyl dec-5-enedioate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以92%的产率得到trans-4-octenedioic acid
  参考文献：
  名称：

  Targeting the Heat Shock Protein 90 Dimer with Dimeric Inhibitors

  摘要：

  The design, synthesis, and biological evaluation of conformationally constrained coumermycin Al analogues are reported. Compounds were evaluated against both breast cancer (SKBr3 and MCF7) and prostate cancer (PC3 mm2, A549, and HT29) cell lines. Non-noviosylated coumermycin Al analogues that manifest potent antiproliferative activity resulting from Hsp90 inhibition are provided, wherein replacement of the stereochemically complex noviose sugar with readily available piperidine rings resulted in similar to 100 fold increase in antiproliferative activities as compared to coumermycin Al, producing small molecule Hsp90 inhibitors that exhibit nanomolar activities.

  DOI：

  10.1021/jm200553w
• 作为产物：
  描述：

  benzyl hex-5-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以62%的产率得到(E)-1,10-dibenzyl dec-5-enedioate
  参考文献：
  名称：

  Targeting the Heat Shock Protein 90 Dimer with Dimeric Inhibitors

  摘要：

  The design, synthesis, and biological evaluation of conformationally constrained coumermycin Al analogues are reported. Compounds were evaluated against both breast cancer (SKBr3 and MCF7) and prostate cancer (PC3 mm2, A549, and HT29) cell lines. Non-noviosylated coumermycin Al analogues that manifest potent antiproliferative activity resulting from Hsp90 inhibition are provided, wherein replacement of the stereochemically complex noviose sugar with readily available piperidine rings resulted in similar to 100 fold increase in antiproliferative activities as compared to coumermycin Al, producing small molecule Hsp90 inhibitors that exhibit nanomolar activities.

  DOI：

  10.1021/jm200553w

文献信息

• In Situ Methylene Capping: A General Strategy for Efficient Stereoretentive Catalytic Olefin Metathesis. The Concept, Methodological Implications, and Applications to Synthesis of Biologically Active Compounds
  作者：Chaofan Xu、Xiao Shen、Amir H. Hoveyda

  DOI：10.1021/jacs.7b06552

  日期：2017.8.9

  catalyst-controlled stereoselective olefin metathesis considerably. By incorporation of commercially available Z-butene together with robust and readily accessible Ru-based dithiolate catalysts developed in these laboratories, a large variety of transformations can be made to proceed with terminal alkenes, without the need for a priori synthesis of a stereochemically defined disubstituted olefin. Reactions thus proceed

  原位亚甲基封端作为一种实用且广泛适用的策略被引入，可以显着扩大催化剂控制的立体选择性烯烃复分解的范围。通过将市售的 Z-丁烯与这些实验室开发的坚固且易于获得的基于 Ru 的二硫醇催化剂结合，可以进行多种转化以处理末端烯烃，而无需先验合成立体化学定义的双取代烯烃。因此，与使用其他基于 Ru、Mo 或 W 的配合物相比，反应以显着更高的效率和 Z 选择性进行。与含有羧酸、醛、烯丙醇、芳基烯烃、α取代基的烯烃交叉复分解，或氨基酸残基以 47-88% 的产率和 90:10 至 >98:2 的 Z:E 选择性生成所需产物。使用 70:30 Z-:E-丁烯混合物（原油裂解的副产品），转化同样有效且具有立体选择性。原位亚甲基封端策略与相同的儿茶酚硫醇配合物（无需催化剂修饰）一起进行闭环复分解反应，以 40-70% 的产率和 96:4-98 的产率生成 14 至 21 元环大环烯烃:2 Z:E 选择性；与