(2E,4E)-5-Trimethylsilanyl-penta-2,4-dienoic acid | 73639-46-0

• 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: (2E,4E)-5-Trimethylsilanyl-penta-2,4-dienoic acid
• 英文别名: (2E,4E)-5-trimethylsilylpenta-2,4-dienoic acid
• CAS: 73639-46-0
• 化学式: C₈H₁₄O₂Si
• 分子量: 170.283
• InChiKey: HCXQKJMRBXVDCH-YDFGWWAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  、 (2E,4E)-5-Trimethylsilanyl-penta-2,4-dienoic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以77%的产率得到(S)-methyl 3-(4-hydroxy-2-methoxy)-2-((2E,4E)-5-(trimethylsilyl)penta-2,4-dienamido)propanoate
  参考文献：
  名称：

  A Strategy for the Late-Stage Divergent Syntheses of Scyphostatin Analogues

  摘要：

  This account details the synthesis of two scyphostatin analogues exhibiting a reactive polar epoxycyclohexenone core and various amide side chains outfitted for late-stage chemical derivatization into the desirable lipophilic tails. Our efforts highlight a key ipso-dearomatization process and provide new insights regarding the incompatibility and orthogonal reactivity of scyphostatin's functional groups. We further showcase the utility of resorcinol derived 2,5-cyclohexadienones as synthetic platforms capable of participating in selective chemical reactivity, and we further demonstrate their potential for rapid elaboration into complex structural motifs,

  DOI：

  10.1021/jo102327e
• 作为产物：
  描述：

  ethyl E,E-5-(trimethylsilyl)-2,4-pentadienoate 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 生成 (2E,4E)-5-Trimethylsilanyl-penta-2,4-dienoic acid
  参考文献：
  名称：

  Nesterov, N. I.; Belyaev, N. N.; Stadnichuk, M. D., Journal of general chemistry of the USSR, 1980, vol. 50, # 1, p. 63 - 72

  摘要：

  DOI：

文献信息

• HECTEPOB N. I.; BELYAEV N. N.; STADNICHUK M. D.; MINGALEVA K. S.; SIGOLAE+, ZH. OBSHCH. XIMII, 1980, 50, HO 1, 76-88
  作者：HECTEPOB N. I.、 BELYAEV N. N.、 STADNICHUK M. D.、 MINGALEVA K. S.、 SIGOLAE+

  DOI：——

  日期：——
• Nesterov, N. I.; Belyaev, N. N.; Stadnichuk, M. D., Journal of general chemistry of the USSR, 1980, vol. 50, # 1, p. 63 - 72
  作者：Nesterov, N. I.、Belyaev, N. N.、Stadnichuk, M. D.、Mingaleva, K. S.、Sigolaev, Yu. F.

  DOI：——

  日期：——
• A Strategy for the Late-Stage Divergent Syntheses of Scyphostatin Analogues
  作者：Jacob Y. Cha、G. Leslie Burnett、Yaodong Huang、Jarrod B. Davidson、Thomas R. R. Pettus

  DOI：10.1021/jo102327e

  日期：2011.3.4

  This account details the synthesis of two scyphostatin analogues exhibiting a reactive polar epoxycyclohexenone core and various amide side chains outfitted for late-stage chemical derivatization into the desirable lipophilic tails. Our efforts highlight a key ipso-dearomatization process and provide new insights regarding the incompatibility and orthogonal reactivity of scyphostatin's functional groups. We further showcase the utility of resorcinol derived 2,5-cyclohexadienones as synthetic platforms capable of participating in selective chemical reactivity, and we further demonstrate their potential for rapid elaboration into complex structural motifs,