(2E,4E)-methyl 5-bromo-4-methylpenta-2,4-dienoate | 1312938-51-4

• 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)-methyl 5-bromo-4-methylpenta-2,4-dienoate
• 英文别名: methyl (2E,4E)-5-bromo-4-methylpenta-2,4-dienoate
• CAS: 1312938-51-4
• 化学式: C₇H₉BrO₂
• 分子量: 205.051
• InChiKey: ZLWYWTPYHKVRJN-VNKDHWASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4E)-methyl 5-bromo-4-methylpenta-2,4-dienoate 在 咪唑 、 sodium chlorite 、 sodium dihydrogenphosphate 、 lithium aluminium tetrahydride 、 1,3,5-三甲氧基苯 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 水 、 manganese triacetate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.17h， 生成 (+)-trichostatic acid
  参考文献：
  名称：

  Concise, Convergent Syntheses of (±)-Trichostatin A Utilizing a Pd-Catalyzed Ketone Enolate α-Alkenylation Reaction

  摘要：

  Two concise, convergent syntheses of (+/-)-trichostatin A (1), a potent histone deacetylase inhibitor, have been accomplished. The key step in both is a Pd-catalyzed alpha-alkenylation reaction between ketone 2 and either dienyl bromide 3 or alkenyl bromide 9 using a modification of cross-coupling conditions described by Negishi and Hartwig. A brief investigation has shown the potential utility of a Ni-catalyzed version of this reaction. The overall synthetic routes are short and amenable to scaleup, providing access to trichostatin A via trichostatic acid as a direct precursor.

  DOI：

  10.1021/ol200964m
• 作为产物：
  描述：

  (E)-3-bromomethacrolein 、 甲氧羰基亚甲基三苯基正膦 以 二氯甲烷 为溶剂， 以4.02 g的产率得到(2E,4E)-methyl 5-bromo-4-methylpenta-2,4-dienoate
  参考文献：
  名称：

  Concise, Convergent Syntheses of (±)-Trichostatin A Utilizing a Pd-Catalyzed Ketone Enolate α-Alkenylation Reaction

  摘要：

  Two concise, convergent syntheses of (+/-)-trichostatin A (1), a potent histone deacetylase inhibitor, have been accomplished. The key step in both is a Pd-catalyzed alpha-alkenylation reaction between ketone 2 and either dienyl bromide 3 or alkenyl bromide 9 using a modification of cross-coupling conditions described by Negishi and Hartwig. A brief investigation has shown the potential utility of a Ni-catalyzed version of this reaction. The overall synthetic routes are short and amenable to scaleup, providing access to trichostatin A via trichostatic acid as a direct precursor.

  DOI：

  10.1021/ol200964m

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。