(2E,4S,6S)-4,6-dimethyl-2-octenoic acid methyl ester | 164118-46-1

• 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: (2E,4S,6S)-4,6-dimethyl-2-octenoic acid methyl ester
• 英文别名: (E,4S,6S)-4,6-Dimethyl-2-octenoic acid methyl ester；methyl (E,4S,6S)-4,6-dimethyloct-2-enoate
• CAS: 164118-46-1
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: ISQMKYBHJYLCJF-LOSXEJPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4S,6S)-4,6-dimethyl-2-octenoic acid methyl ester 在 4-二甲氨基吡啶 、 lithium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 96.0h， 生成 [1R,3R,8S-(1α,2α(2E,4S,6S),5α,10α,11β)]-2-(4,6-dimethyl-2-octenoyl)-5-methoxy-2,11-dihydroxy-4,9,12-trioxatricyclo[6.3.1.0^3,8]dodecane-1,10,11-tricarboxylic acid 1,10,11-tris(1,1-dimethylethyl) ester
  参考文献：
  名称：

  Total Synthesis of Zaragozic Acid A (Squalestatin S1). Degradation to a Relay Compound and Reassembly of the Natural Product

  摘要：

  Zaragozic acid A (squalestatin S1) (1) was converted into the simpler derivative 2, which was reconverted into the natural product, thus establishing 2 as a viable relay compound for total synthesis of 1. The degradation (Scheme 1) consisted of formation of the tri-tert-butyl ester (3), from which the two side chains were sequentially removed to obtain 8. Aldehyde 8 was converted into dimethyl acetal 2 in standard fashion. The C6 acyl side chain 14 was prepared from (S)-2-methylbutanol (''active amyl alcohol''), and the desired 4S configuration was obtained by use of Evans asymmetric enolate methylation (Scheme 2). The C1 alkyl side chain was prepared as stannane 23a from (R)-2-methyl-3-phenylpropanol (21) as shown in Scheme 5. For conversion of 2 back into zaragozic acid A, the dimethyl acetal was first converted into the cyclic acetal 17, thus protecting the C7 hydroxyl group. The remaining hydroxyl group was then acylated with acid 14 to obtain 18, which was transformed into aldehyde 20 (Scheme 4). The C1 alkyl chain was elaborated by the addition of a chiral alpha-alkoxyorganocerium reagent, obtained from 23a, to aldehyde 20. The resulting mixture of diastereomeric secondary alcohols was converted into zaragozic acid A (1) in six steps (Scheme 6).

  DOI：

  10.1021/jo961533m
• 作为产物：
  描述：

  N-[(S)-2-methoxymethylpyrrolidin-1-yl]propan-1-imine 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 5.01h， 生成 (2E,4S,6S)-4,6-dimethyl-2-octenoic acid methyl ester
  参考文献：
  名称：

  Nicolaou, Kyriacos Costa; Yue, Eddy W.; Naniwa, Yoshimitsu, Angewandte Chemie, 1994, vol. 106, # 21, p. 2306 - 2309

  摘要：

  DOI：

文献信息

• Nicolaou, K. C.; Yue, Eddy W.; Greca, Susan La, Chemistry - A European Journal, 1995, vol. 1, # 7, p. 467 - 494
  作者：Nicolaou, K. C.、Yue, Eddy W.、Greca, Susan La、Nadin, Alan、Yang, Zhen、et al.

  DOI：——

  日期：——