tert-butyl (2E,5S,7E)-5-hydroxy-6-oxo-8-phenylocta-2,7-dienoate | 181656-35-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: tert-butyl (2E,5S,7E)-5-hydroxy-6-oxo-8-phenylocta-2,7-dienoate
• CAS: 181656-35-9
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: MJLVXDINIKQWMB-NTDGVJBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2E,5S,7E)-5-hydroxy-6-oxo-8-phenylocta-2,7-dienoate 在 4-二甲氨基吡啶 、 (苯并三唑-1-基氧基)二哌啶碳鎓六氟磷酸盐 、 trichlorobenzoyl chloride 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 反应 5.25h， 生成 (3S,6R,10S,16S)-3-isobutyl-10-(3-chloro-4-methoxybenzyl)-6-methyl-16-(3-phenylacryloyl)-1,4-dioxa-8,11-diazacyclohexadec-13(E)-ene-2,5,9,12-tetraone
  参考文献：
  名称：

  Total Synthesis of Cryptophycins and Their 16-(3-Phenylacryloyl) Derivatives

  摘要：

  Cryptophycin A, a cyclic depsipeptide isolated from the blue-green alga (cyanobacterium) Nostoc sp.GSV 224, has shown excellent activity against solid tumors implanted in mice. The benzylic epoxide, which was shown to be very important for biological, activity, is also fairly unstable under both acidic and alkaline conditions. The high doses needed to observe in vivo activity might be a result of this instability. In order to solve this problem while preserving the electrophilic character of the benzylic position, enones 1 and 2 have been proposed as promising analogs of the natural product, and a convergent total synthesis of these compounds is described. In addition, the same strategy was used to prepare Cryptophycins A, B, C, and D.

  DOI：

  10.1021/jo960816b
• 作为产物：
  描述：

  lithium phenylacetylide 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 草酰氯 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 作用下， 以 苯 为溶剂， 反应 28.92h， 生成 tert-butyl (2E,5S,7E)-5-hydroxy-6-oxo-8-phenylocta-2,7-dienoate
  参考文献：
  名称：

  Total Synthesis of Cryptophycins and Their 16-(3-Phenylacryloyl) Derivatives

  摘要：

  Cryptophycin A, a cyclic depsipeptide isolated from the blue-green alga (cyanobacterium) Nostoc sp.GSV 224, has shown excellent activity against solid tumors implanted in mice. The benzylic epoxide, which was shown to be very important for biological, activity, is also fairly unstable under both acidic and alkaline conditions. The high doses needed to observe in vivo activity might be a result of this instability. In order to solve this problem while preserving the electrophilic character of the benzylic position, enones 1 and 2 have been proposed as promising analogs of the natural product, and a convergent total synthesis of these compounds is described. In addition, the same strategy was used to prepare Cryptophycins A, B, C, and D.

  DOI：

  10.1021/jo960816b