methyl 5-(1,1,2,2-tetramethyl-1-silapropoxy)hept-6-ynoate | 123808-22-0

• 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: methyl 5-(1,1,2,2-tetramethyl-1-silapropoxy)hept-6-ynoate
• 英文别名: Methyl 5-(tert-butyl)dimethylsilyloxy-6-heptynoate；methyl 5-(t-butyl)dimethyl silyloxy-6-heptynoate；Methyl 5-[tert-butyl(dimethyl)silyl]oxyhept-6-ynoate
• CAS: 123808-22-0
• 化学式: C₁₄H₂₆O₃Si
• 分子量: 270.444
• InChiKey: AZOAIZOTNGTVSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  methyl 5-hydroxyhept-6-ynoate 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以88%的产率得到methyl 5-(1,1,2,2-tetramethyl-1-silapropoxy)hept-6-ynoate
  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

文献信息

• Total synthesis of (+)-Leukotriene B4 methyl ester and its 5-epimer from (R)-glycidol
  作者：M. Avignon-Tropis、M. Treilhou、J.R. Pougny、I. Fréchard-Ortuno、G. Linstrumelle

  DOI：10.1016/s0040-4020(01)89730-1

  日期：1991.8

  The Pd-Cu coupling reaction of a chiral hydroxy-(E,E)-iododiene with a racemic acetylenic alcohol followed by reduction of the dienyne leads to the desired (Z,E,E) geometry and allows synthesis of LTB4 and its 5-epimer after separation of diastereomers.
• Stereoselective synthesis of polyenic alcohols. A new route to the leukotrienes B.
  作者：D Guillerm、C Linstrumelle

  DOI：10.1016/s0040-4039(00)85346-0

  日期：1986.1