5-(1,1,2,2-tetramethyl-1-silapropoxy)hept-6-yn-1-ol | 220556-85-4

• 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: 5-(1,1,2,2-tetramethyl-1-silapropoxy)hept-6-yn-1-ol
• 英文别名: 5-[Tert-butyl(dimethyl)silyl]oxyhept-6-yn-1-ol
• CAS: 220556-85-4
• 化学式: C₁₃H₂₆O₂Si
• 分子量: 242.434
• InChiKey: VOSUCMMKHMNPBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙烯基乙醚 、 5-(1,1,2,2-tetramethyl-1-silapropoxy)hept-6-yn-1-ol 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到1-(1-ethoxyethoxy)-5-(1,1,2,2-tetramethyl-1-silapropoxy)hept-6-yne
  参考文献：
  名称：

  Total Synthesis of Iso[7]-Levuglandin D₂

  摘要：

  Iso[7]-levuglandin D-2 (iso[7]-LGD(2), 9-acetyl-8-formyl-5-hydroxy-6(E), 11(Z)-heptadecadienoic acid) is a structural isomer of levuglandin D-2 (9-acetyl-8-formyl-12-hydroxy-5(Z), 10(E)-heptadecadienoic acid) that we postulate-to be generated during nonenzymatic free radical-induced oxidation of arachidonic acid. To facilitate detection and identification in biological samples, a total synthesis of iso[7]-LGD(2) was devised. The functionality in iso[7]-LGD(2) is diverse and chemically sensitive, and an acid-catalyzed lactonization of the allylically activated delta-hydroxy acid array present in the synthetic target was encountered that occurs readily in aqueous solution. Nevertheless, conjugate addition of a multifunctional vinyl cyanocuprate to achieve the final carbon-carbon bond-forming step, followed by a sequence of functional and protecting group manipulations, reproducibly delivered a readily separable 3:7 mixture of iso[7]-LGD(2) lactone and the free acid.

  DOI：

  10.1021/jo981929t
• 作为产物：
  描述：

  methyl 5-(1,1,2,2-tetramethyl-1-silapropoxy)hept-6-ynoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以85%的产率得到5-(1,1,2,2-tetramethyl-1-silapropoxy)hept-6-yn-1-ol
  参考文献：
  名称：

  Total Synthesis of Iso[7]-Levuglandin D₂

  摘要：

  Iso[7]-levuglandin D-2 (iso[7]-LGD(2), 9-acetyl-8-formyl-5-hydroxy-6(E), 11(Z)-heptadecadienoic acid) is a structural isomer of levuglandin D-2 (9-acetyl-8-formyl-12-hydroxy-5(Z), 10(E)-heptadecadienoic acid) that we postulate-to be generated during nonenzymatic free radical-induced oxidation of arachidonic acid. To facilitate detection and identification in biological samples, a total synthesis of iso[7]-LGD(2) was devised. The functionality in iso[7]-LGD(2) is diverse and chemically sensitive, and an acid-catalyzed lactonization of the allylically activated delta-hydroxy acid array present in the synthetic target was encountered that occurs readily in aqueous solution. Nevertheless, conjugate addition of a multifunctional vinyl cyanocuprate to achieve the final carbon-carbon bond-forming step, followed by a sequence of functional and protecting group manipulations, reproducibly delivered a readily separable 3:7 mixture of iso[7]-LGD(2) lactone and the free acid.

  DOI：

  10.1021/jo981929t