4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-oxo-ethyl)-butyric acid tert-butyl ester | 126822-60-4

• 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: 4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-oxo-ethyl)-butyric acid tert-butyl ester
• 英文别名: tert-butyl 2-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-4-oxobutanoate
• CAS: 126822-60-4
• 化学式: C₂₆H₃₆O₄Si
• 分子量: 440.655
• InChiKey: LHOUNBCMMDEQND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-oxo-ethyl)-butyric acid tert-butyl ester 在 sodium tetrahydroborate 、 D(+)-10-樟脑磺酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 1.17h， 生成 α-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>butyrolactone
  参考文献：
  名称：

  Paquette, Leo A.; Doherty, Annette M.; Rayner, Christopher M., Journal of the American Chemical Society, 1992, vol. 114, # 10, p. 3910 - 3926

  摘要：

  DOI：
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 4-二甲氨基吡啶 、 N,N-二甲基丙烯基脲 、 臭氧 、 三乙胺 、 三苯基膦 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 86.17h， 生成 4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-oxo-ethyl)-butyric acid tert-butyl ester
  参考文献：
  名称：

  Paquette, Leo A.; Doherty, Annette M.; Rayner, Christopher M., Journal of the American Chemical Society, 1992, vol. 114, # 10, p. 3910 - 3926

  摘要：

  DOI：

文献信息

• PAQUETTE, LEO A.;RAYNER, CHRISTOPHER M.;DOHERTY, ANNETTE M., J. AMER. CHEM. SOC., 112,(1990) N0, C. 4078-4079
  作者：PAQUETTE, LEO A.、RAYNER, CHRISTOPHER M.、DOHERTY, ANNETTE M.

  DOI：——

  日期：——
• Total synthesis of furanocembranolides. 3. A concise convergent route to acerosolide
  作者：Leo A. Paquette、Peter C. Astles

  DOI：10.1021/jo00053a031

  日期：1993.1

  The first synthesis of a 14-membered furanocembranolide has been achieved. The target molecule, acerosolide, contains two stereogenic cetners whose relative and absolute configuration have not previously been assigned. MM2 calculations performed during the course of the present work suggest their configuration to be 1(S*),10(R*). The synthesis began by SnCl2-promoted condensation of allylstannane 6 to aldehyde 7 so as to achieve regioreversed condensation and formation of the extended allylic alcohol 9. Acid-catalyzed lactonization and 2-fold oxidation via the bis-selenide gave butenolide 11 and subsequently the derived bromide 12b. Palladium(0)-catalyzed condensation of 12b with vinylstannane 13 provided seco-cembrane 14. Following the elaboration of 14 into bromo aldehyde 16, macrocyclization was effected with chromous chloride. The single homoallylic alcohol produced by this means underwent oxidation to give acerosolide, as deduced by proper spectral comparison with the natural product.