4-methoxybenzyl (2E,4E)-7-(4-(dimethylamino)phenyl)-4,6-dimethyl-7-oxohepta-2,4-dienoate | 1312938-58-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxybenzyl (2E,4E)-7-(4-(dimethylamino)phenyl)-4,6-dimethyl-7-oxohepta-2,4-dienoate
• 英文别名: (±)-(2E,4E)-methoxybenzyl 7-(4-(dimethylamino)phenyl)-4,6-dimethyl-7-oxohepta-2,4-dienoate；(4-methoxyphenyl)methyl (2E,4E)-7-[4-(dimethylamino)phenyl]-4,6-dimethyl-7-oxohepta-2,4-dienoate
• CAS: 1312938-58-1
• 化学式: C₂₅H₂₉NO₄
• 分子量: 407.51
• InChiKey: OOZVJKUVIAAWTQ-ZDNQDDNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methoxybenzyl (2E,4E)-7-(4-(dimethylamino)phenyl)-4,6-dimethyl-7-oxohepta-2,4-dienoate 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以96%的产率得到(+)-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：

  1-(4-(dimethylamino)phenyl)propan-1-ol 在 2,2,6,6-tetramethylpiperidinyl-lithium 、 manganese triacetate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.33h， 生成 4-methoxybenzyl (2E,4E)-7-(4-(dimethylamino)phenyl)-4,6-dimethyl-7-oxohepta-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

• Ni-Catalyzed Alkenylation of Ketone Enolates under Mild Conditions: Catalyst Identification and Optimization
  作者：Michael Grigalunas、Tobias Ankner、Per-Ola Norrby、Olaf Wiest、Paul Helquist

  DOI：10.1021/jacs.5b02945

  日期：2015.6.10

  A procedure for Ni-catalyzed cross-coupling of ketone enolates with alkenyl halides has been developed. Intermolecular coupling of aromatic and aliphatic ketone lithium enolates with a variety of alkenyl halides is achieved in the presence of Ni(cod)(2) catalyst (5 mol %), an N-heterocyclic carbene (NHC) ligand, and LiI (10 mol %) at 6-22 degrees C for 0.5-12 h with yields of up to 90%. During the initial development of this reaction, a misleading result with respect to the actual active catalyst was obtained using commercially available Q:Phos ligand, which was found to contain a trace of Pd metal contaminant sufficient to catalyze the reaction. However, under the final conditions optimized for Ni(cod)(2) in the presence of an NHC ligand, Pd was incompetent as a catalyst.
• Concise, Convergent Syntheses of (±)-Trichostatin A Utilizing a Pd-Catalyzed Ketone Enolate α-Alkenylation Reaction
  作者：Casey C. Cosner、Paul Helquist

  DOI：10.1021/ol200964m

  日期：2011.7.15

  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.