methyl (2E,4E)-7-[4-(dimethylamino)phenyl]-7-methoxy-4,6-dimethylhepta-2,4-dienoate | 1208355-93-4

• 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]-7-methoxy-4,6-dimethylhepta-2,4-dienoate
• CAS: 1208355-93-4
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: HQKVPQZWBNFPFZ-MZXMXVKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2E,4E)-7-[4-(dimethylamino)phenyl]-7-methoxy-4,6-dimethylhepta-2,4-dienoate 在 水 、 lithium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以100%的产率得到(2E,4E)-7-[4-(dimethylamino)phenyl]-7-methoxy-4,6-dimethylhepta-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
• 作为产物：
  描述：

  (+/-)-4-(1-methoxy-2-methylpent-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 4.5h， 以81%的产率得到methyl (2E,4E)-7-[4-(dimethylamino)phenyl]-7-methoxy-4,6-dimethylhepta-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

文献信息

• SYNTHESIS OF HDAC INHIBITORS: TRICHOSTATIN A AND ANALOGUES
  申请人：Helquist Paul

  公开号：US20110237832A1

  公开（公告）日：2011-09-29

  Embodiments herein relate to histone deacetylaces (HDACs) and HDAC inhibitors, such as trichostatin A (TSA) and TSA analogues. Embodiments provide simple methods of synthesizing TSA and TSA analogues. These methods provide routes of synthesis of TSA and TSA analogues that enable the production of the HDAC inhibitors at lower cost and in greater quantities than previously were available.

  本文涉及组蛋白去乙酰化酶（HDACs）和HDAC抑制剂，如三氯乙酸（TSA）及其类似物。实施例提供了合成TSA和TSA类似物的简单方法。这些方法提供了合成TSA和TSA类似物的途径，使得生产HDAC抑制剂的成本更低、数量更大，比以往更容易获得。
• 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.