(2E,4E)-7-[4-(dimethylamino)phenyl]-4-ethyl-6-methyl-7-oxohepta-2,4-dienoic acid | 1208355-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E,4E)-7-[4-(dimethylamino)phenyl]-4-ethyl-6-methyl-7-oxohepta-2,4-dienoic acid
• CAS: 1208355-95-6
• 化学式: C₁₈H₂₃NO₃
• 分子量: 301.386
• InChiKey: GCBLIXZIQVXLIF-RGNKTVKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.25h， 以91%的产率得到(2E,4E)-7-[4-(dimethylamino)phenyl]-4-ethyl-6-methyl-7-oxohepta-2,4-dienoic acid
  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

文献信息

• An Efficient Synthesis of (±)-Trichostatic Acid and Analogues: A New Route to (±)-Trichostatin A
  作者：Anamitra Chatterjee、Joshua Richer、Tyler Hulett、Vijaya Bhaskara Reddy Iska、Olaf Wiest、Paul Helquist

  DOI：10.1021/ol9029116

  日期：2010.2.19

  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.