4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)cyclopent-2-en-1-one | 1309655-83-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)cyclopent-2-en-1-one
• CAS: 1309655-83-1
• 化学式: C₂₃H₂₈O₂Si
• 分子量: 364.56
• InChiKey: PTGUQIIDDYNGAD-UHFFFAOYSA-N

物化性质

• 沸点：
  443.1±28.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)cyclopent-2-en-1-one 在 盐酸 、 sodium tetrahydroborate 、 copper(l) iodide 、 水 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.83h， 生成
  参考文献：
  名称：

  Convenient Synthesis of the Key Intermediate for Dihydrocorynantheol and Protoemetinol from the Monoacetate of 4-Cyclopentene-1,3-diol

  摘要：

  We invented an efficient method to obtain the key delta-lactone possessing the (CH(2))(2)OTBDPS and Et groups at C3 and C4, respectively, starting with the acetate of 4-cyclopentene-1,3-diol, which was subjected to Pd-catalyzed allylation with malonate anion to attach the (CH(2))(2)OTBDPS group. The Et group was then installed by 1,4-addition to the derived enone. Finally, the resulting enol TMS ether was oxidized to afford the lactone. Furthermore, the lactone was converted to dihydrocorynantheol and protoemetinol, both of which are typical examples of indoloquinolizidine and benzo[a]quinolizine alkaloids.

  DOI：

  10.3987/com-10-s(e)109
• 作为产物：
  描述：

  2-((1s,4s)-4-羟基-2-环戊烯基)乙酸甲酯 在 咪唑 、 lithium aluminium tetrahydride 、 Jones reagent 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)cyclopent-2-en-1-one
  参考文献：
  名称：

  Convenient Synthesis of the Key Intermediate for Dihydrocorynantheol and Protoemetinol from the Monoacetate of 4-Cyclopentene-1,3-diol

  摘要：

  We invented an efficient method to obtain the key delta-lactone possessing the (CH(2))(2)OTBDPS and Et groups at C3 and C4, respectively, starting with the acetate of 4-cyclopentene-1,3-diol, which was subjected to Pd-catalyzed allylation with malonate anion to attach the (CH(2))(2)OTBDPS group. The Et group was then installed by 1,4-addition to the derived enone. Finally, the resulting enol TMS ether was oxidized to afford the lactone. Furthermore, the lactone was converted to dihydrocorynantheol and protoemetinol, both of which are typical examples of indoloquinolizidine and benzo[a]quinolizine alkaloids.

  DOI：

  10.3987/com-10-s(e)109