methyl (2E,4E)-7-(4-(dimethylamino)phenyl)-4-ethyl-7-methoxy-6-methylhepta-2,4-dienoate | 1208356-02-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2E,4E)-7-(4-(dimethylamino)phenyl)-4-ethyl-7-methoxy-6-methylhepta-2,4-dienoate
• CAS: 1208356-02-8
• 化学式: C₂₀H₂₉NO₃
• 分子量: 331.455
• InChiKey: IPEWGMLWCHVAON-LZKYXZFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (2E,4E)-7-(4-(dimethylamino)phenyl)-4-ethyl-7-methoxy-6-methylhepta-2,4-dienoate 在 水 、 lithium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以100%的产率得到
  参考文献：
  名称：

  An Efficient Synthesis of (±)-Trichostatic Acid and Analogues: A New Route to (±)-Trichostatin A

  摘要：

  An efficient synthesis of rac-trichostatic acid (1) and its analogues Is reported starting from a commercially available aldehyde. Further manipulations of rac-1 led to rac-trichostatin A (TSA). Construction of the desired molecular architecture entails a two-component union, achieved through an in situ hydroboration followed by a Suzuki-Miyaura coupling with 2. The requisite homopropargyl alcohol was synthesized by exploiting allenylindium chemistry. This new protocol paved the way for the synthesis of analogues of trichostatic acid and hence TSA.

  DOI：

  10.1021/ol9029116
• 作为产物：
  描述：

  4-(1-methoxy-2-methylhex-3-ynyl)-N,N-dimethylaniline 、 Methyl 3-bromopropenoate 在 diisopinocampheylborane 、 甲醇 、 四(三苯基膦)钯 、 thallium (I) ethoxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以81%的产率得到methyl (2E,4E)-7-(4-(dimethylamino)phenyl)-4-ethyl-7-methoxy-6-methylhepta-2,4-dienoate
  参考文献：
  名称：

  An Efficient Synthesis of (±)-Trichostatic Acid and Analogues: A New Route to (±)-Trichostatin A

  摘要：

  An efficient synthesis of rac-trichostatic acid (1) and its analogues Is reported starting from a commercially available aldehyde. Further manipulations of rac-1 led to rac-trichostatin A (TSA). Construction of the desired molecular architecture entails a two-component union, achieved through an in situ hydroboration followed by a Suzuki-Miyaura coupling with 2. The requisite homopropargyl alcohol was synthesized by exploiting allenylindium chemistry. This new protocol paved the way for the synthesis of analogues of trichostatic acid and hence TSA.

  DOI：

  10.1021/ol9029116