4-(2,6-二甲基苯基)丁烷-2-酮 | 832712-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(2,6-二甲基苯基)丁烷-2-酮
• 英文名称: 4-(2,6-dimethylphenyl)butan-2-one
• CAS: 832712-90-0
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: QZDBKSCHXHWOMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(2,6-二甲基苯基)丁烷-2-酮 在 chromium dichloride 、 盐酸 、 水 、 双(三甲基硅烷基)氨基钾 、 nickel dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 UTKO5
  参考文献：
  名称：

  Synthesis and anti-migrative evaluation of moverastin derivatives

  摘要：

  Cell migration of tumor cells is essential for invasion of the extracellular matrix and for cell dissemination. Inhibition of the cell migration involved in the invasion process represents a potential therapeutic approach to the treatment of tumor metastasis; therefore, a novel series of derivatives of moverastins (moverastins A and B), an inhibitor of tumor cell migration, was designed and chemically synthesized. Among these moverastin derivatives, several compounds showed stronger cell migration inhibitory activity than parental moverastins, and UTKO1 was found to have the most potent inhibitory activity against the migration of human esophageal tumor EC17 cells in a chemotaxis cell chamber assay. Interestingly, although moverastins are considered to inhibit tumor cell migration by inhibiting farnesyltransferase (FTase), UTKO1 did not inhibit FTase, indicating that UTKO1 inhibited tumor cell migration by a mechanism other than the inhibition of FTase. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.028
• 作为产物：
  描述：

  2,6-二甲基溴苯 在 palladium diacetate 、 钯 氢气 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(2,6-二甲基苯基)丁烷-2-酮
  参考文献：
  名称：

  Latia荧光素类似物的生物发光活性：将2,6,6-三甲基环己烯环取代到甲基取代的苯基上

  摘要：

  合成了一系列具有甲基取代的苯基而不是天然的2,6,6-三甲基己烯环的羊毛素荧光素类似物，并测量了它们的生物发光活性。所述Latia萤光素酶被发现是能够适度地识别适当的甲基取代的苯基类似物具有相同的光的产生的动力学作为天然荧光素。

  DOI：

  10.1016/j.tetlet.2004.11.043

文献信息

• Controlling Olefin Isomerization in the Heck Reaction with Neopentyl Phosphine Ligands
  作者：Matthew G. Lauer、Mallory K. Thompson、Kevin H. Shaughnessy

  DOI：10.1021/jo501840u

  日期：2014.11.21

  The use of neopentyl phosphine ligands was examined in the coupling of aryl bromides with alkenes. Di-tert-butylneopentylphosphine (DTBNpP) was found to promote Heck couplings with aryl bromides at ambient temperature. In the Heck coupling of cyclic alkenes, the degree of alkene isomerization was found to be controlled by the choice of ligand with DTBNpP promoting isomerization to a much greater extent than trineopentylphosphine (TNpP). Under optimal conditions, DTBNpP provides high selectivity for 2-aryl-2,3-dihydrofuran in the arylation of 2,3-dihydrofuran, whereas TNpP provided high selectivity for the isomeric 2-aryl-2,5-dihydrofuran. A similar complementary product selectivity is seen in the Heck coupling of cyclopentene. Heck coupling of 2-bromophenols or 2-bromoanilides with 2,3-dihydrofurans affords 2,5-epoxybenzoxepin and 2,5-epoxybenzazepins, respectively.
• Bioluminescence activity of Latia luciferin analogues: replacement of the 2,6,6-trimethylcyclohexene ring onto the methyl-substituted phenyl groups
  作者：Mitsuhiro Nakamura、Masashi Mamino、Mizuki Masaki、Shojiro Maki、Ryo Matsui、Satoshi Kojima、Takashi Hirano、Yoshihiro Ohmiya、Haruki Niwa

  DOI：10.1016/j.tetlet.2004.11.043

  日期：2005.1

  A series of Latia luciferin analogues having methyl-substituted phenyl groups instead of the natural 2,6,6-trimethylhexene ring was synthesized and their bioluminescence activity were measured. The Latia luciferase was found to be able to moderately recognize the appropriately methyl-substituted phenyl analogues with the same light production kinetics as that of natural luciferin.

  合成了一系列具有甲基取代的苯基而不是天然的2,6,6-三甲基己烯环的羊毛素荧光素类似物，并测量了它们的生物发光活性。所述Latia萤光素酶被发现是能够适度地识别适当的甲基取代的苯基类似物具有相同的光的产生的动力学作为天然荧光素。
• Synthesis and anti-migrative evaluation of moverastin derivatives
  作者：Masato Sawada、Shin-ichiro Kubo、Koji Matsumura、Yasushi Takemoto、Hiroki Kobayashi、Etsu Tashiro、Takeshi Kitahara、Hidenori Watanabe、Masaya Imoto

  DOI：10.1016/j.bmcl.2011.01.028

  日期：2011.3

  Cell migration of tumor cells is essential for invasion of the extracellular matrix and for cell dissemination. Inhibition of the cell migration involved in the invasion process represents a potential therapeutic approach to the treatment of tumor metastasis; therefore, a novel series of derivatives of moverastins (moverastins A and B), an inhibitor of tumor cell migration, was designed and chemically synthesized. Among these moverastin derivatives, several compounds showed stronger cell migration inhibitory activity than parental moverastins, and UTKO1 was found to have the most potent inhibitory activity against the migration of human esophageal tumor EC17 cells in a chemotaxis cell chamber assay. Interestingly, although moverastins are considered to inhibit tumor cell migration by inhibiting farnesyltransferase (FTase), UTKO1 did not inhibit FTase, indicating that UTKO1 inhibited tumor cell migration by a mechanism other than the inhibition of FTase. (C) 2011 Elsevier Ltd. All rights reserved.