(E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-3,4-dimethyl-hept-2-enoic acid (S)-4-methyl-2-methylene-5-oxo-hexyl ester | 791131-47-0

• 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: (E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-3,4-dimethyl-hept-2-enoic acid (S)-4-methyl-2-methylene-5-oxo-hexyl ester
• 英文别名: [(4S)-4-methyl-2-methylidene-5-oxohexyl] (E,4R)-7-[tert-butyl(diphenyl)silyl]oxy-3,4-dimethylhept-2-enoate
• CAS: 791131-47-0
• 化学式: C₃₃H₄₆O₄Si
• 分子量: 534.811
• InChiKey: CUMFRMMFVUUBIH-REYQOFRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.64
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-3,4-dimethyl-hept-2-enoic acid (S)-4-methyl-2-methylene-5-oxo-hexyl ester 在 臭氧 、 二甲基硫 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以48%的产率得到(E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-3,4-dimethyl-hept-2-enoic acid (S)-4-methyl-2,5-dioxo-hexyl ester
  参考文献：
  名称：

  Syntheses of the C(1−6) and C(19−24) Fragments of Lituarines A, B, and C

  摘要：

  Lituarines A-C are marine natural products comprising a tricyclic spiroacetal bridged at C(8) and C(18) by a functionalized ester linkage conceptually obtained from a C(19-24) alcohol and a C(1-6) carboxylic acid whose oxidation level varies at C(4) and C(5). Stereoselective routes are described to compounds 26 and 27, fully functionalized ester fragments of lituarine A and lituarines B and C, respectively.

  DOI：

  10.1021/ol048396x
• 作为产物：
  描述：

  1-(t-butyldiphenylsilyloxy)-3-iodopropane 在 正丁基锂 、 草酰氯 、 三氟乙酸 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.25h， 生成 (E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-3,4-dimethyl-hept-2-enoic acid (S)-4-methyl-2-methylene-5-oxo-hexyl ester
  参考文献：
  名称：

  Syntheses of the C(1−6) and C(19−24) Fragments of Lituarines A, B, and C

  摘要：

  Lituarines A-C are marine natural products comprising a tricyclic spiroacetal bridged at C(8) and C(18) by a functionalized ester linkage conceptually obtained from a C(19-24) alcohol and a C(1-6) carboxylic acid whose oxidation level varies at C(4) and C(5). Stereoselective routes are described to compounds 26 and 27, fully functionalized ester fragments of lituarine A and lituarines B and C, respectively.

  DOI：

  10.1021/ol048396x

文献信息

• Syntheses of the C(1−6) and C(19−24) Fragments of Lituarines A, B, and C
  作者：Jeremy Robertson、Jonathan W. P. Dallimore、Paul Meo

  DOI：10.1021/ol048396x

  日期：2004.10.1

  Lituarines A-C are marine natural products comprising a tricyclic spiroacetal bridged at C(8) and C(18) by a functionalized ester linkage conceptually obtained from a C(19-24) alcohol and a C(1-6) carboxylic acid whose oxidation level varies at C(4) and C(5). Stereoselective routes are described to compounds 26 and 27, fully functionalized ester fragments of lituarine A and lituarines B and C, respectively.