3,3-Dimethyl-5-phenyl-pentan-2-on | 1014-88-6

• 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: 3,3-Dimethyl-5-phenyl-pentan-2-on
• 英文别名: 3,3-Dimethyl-5-phenylpentan-2-one
• CAS: 1014-88-6
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: VSMKJVOGARYTPB-UHFFFAOYSA-N

物化性质

• 沸点：
  103 °C(Press: 2 Torr)
• 密度：
  0.942±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  3,3-Dimethyl-5-phenyl-pentan-2-on 在 氢溴酸 作用下， 生成 1,2,3-三甲基萘
  参考文献：
  名称：

  Quillet,J.-P.; Dreux,J., Bulletin de la Societe Chimique de France, 1966, p. 645 - 652

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-Dimethyl-5-phenyl-pentan-2,3-diol 在 甲酸 作用下， 生成 3,3-Dimethyl-5-phenyl-pentan-2-on
  参考文献：
  名称：

  Quillet,J.-P.; Dreux,J., Bulletin de la Societe Chimique de France, 1966, p. 645 - 652

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed C–H Silylation of Aliphatic Ketones Using an Aminooxyamide Auxiliary
  作者：Jianhua Li、Chao Jiang

  DOI：10.1021/acs.orglett.1c01678

  日期：2021.7.16

  A palladium-catalyzed β-C(sp3)–H silylation of aliphatic ketones with disilanes to afford β-silyl ketones is reported. The aminooxyamide auxiliary is critical for the C–H activation and silylation. The reaction tolerates a number of functional groups and shows good selectivity in silylating β-C(sp3)–H bonds in the company of C(sp2)–H bonds and acidic α-C(sp3)–H bonds. The reaction is scalable, and

  据报道，钯催化的脂肪族酮与乙硅烷的β-C(sp 3 )-H 甲硅烷基化反应得到 β-甲硅烷基酮。氨基氧酰胺助剂对于 C-H 活化和硅烷化至关重要。该反应耐受许多官能团，并在C(sp 2 )-H 键和酸性 α-C(sp 3 )-H 键的陪伴下对 β-C(sp 3 )-H 键进行甲硅烷基化显示出良好的选择性。该反应是可扩展的，并且很容易去除氨基氧酰胺助剂以得到 β-甲硅烷基酮，它可以作为有机合成的有用结构单元。使用该协议的后期多样化在 santonin 的甲硅烷基化中得到了很好的证明。
• Influence of Geminal Disubstitution on Samarium Diiodide Induced Reductive Cyclizations of γ-Aryl Ketones
  作者：Hans-Ulrich Reissig、André Niermann

  DOI：10.1055/s-0030-1259526

  日期：2011.3

  Geminal disubstitution at the alkyl chain of γ-aryl ketones significantly influences the efficacy of samarium diiodide induced cyclizations providing significantly higher yields. β,β-Disubstituted aryl ketones 11a―e and γ,γ-disubstituted aryl ketone 14 could be converted into the corresponding hexahydronaphthalene derivatives in good yields. On the other hand, α,α-disubstituted ketone 9 only gave the

  γ-芳基酮的烷基链处的孪晶脱取代显着影响二碘化钐诱导的环化的功效，从而提供显着更高的产率。β,β-二取代芳基酮11a-e和γ,γ-二取代芳基酮14可以以良好的产率转化为相应的六氢萘衍生物。另一方面，α,α-二取代的酮9只得到仲醇10以及回收的起始材料。含有杂原子取代基的芳基酮也可以高产率环化，底物如 11d 具有空间要求的环状取代基有效地提供了螺环化合物。
• Zn2Motif-Tethered Short-Chain Fatty Acids as a Novel Class of Histone Deacetylase
  申请人：Chen Ching-Shih

  公开号：US20070225373A1

  公开（公告）日：2007-09-27

  Zn 2+ -chelating motif-tethered fatty acids as histone deacetylase (HDAC) inhibitors. One hydroxamate-tethered phenylbutyrate compound, N-hydroxy-4-(4-phenylbutyrylamino)-benzamide (HTPB), displayed nM potency in inhibiting HDAC activity. Exposure of several cancer cell lines to HTPB at sub-μM concentrations showed reduced cell proliferation accompanied by histone hyperacetylation and elevated p21 WAF/CIP1 expression, hallmark features associated with intracellular HDAC inhibition.

  Zn2+螯合基固定的脂肪酸作为组蛋白去乙酰化酶（HDAC）抑制剂。一种羟酰胺基固定的苯丁酸化合物，N-羟基-4-(4-苯丁酰氨基)-苯甲酰胺（HTPB），在抑制HDAC活性方面表现出纳摩尔级别的效力。将几种癌细胞系暴露于亚微米浓度的HTPB中，显示出细胞增殖减少，伴随着组蛋白高乙酰化和升高的p21WAF/CIP1表达，这是与细胞内HDAC抑制相关的标志性特征。
• ZN2+Chelating Motif-Tethered Short-Chain Fatty Acids as a Novel Class of Histone Deacetylase Inhibitors
  申请人：Chen Ching-Shih

  公开号：US20090137679A1

  公开（公告）日：2009-05-28

  Zn 2+ -chelating motif-tethered fatty acids as histone deacetylase (HDAC) inhibitors. Compounds performed well in in vitro and in vivo tests.

  以Zn2+螯合基固定的脂肪酸作为组蛋白去乙酰化酶（HDAC）抑制剂。该化合物在体外和体内测试中表现良好。
• Novel selective anti-androgens with a diphenylpentane skeleton
  作者：Keisuke Maruyama、Tomomi Noguchi-Yachide、Kazuyuki Sugita、Yuichi Hashimoto、Minoru Ishikawa

  DOI：10.1016/j.bmcl.2010.09.011

  日期：2010.11

  We have proposed a multi-template approach for drug development, focusing on similar fold structures of proteins, and have effectively generated lead compounds for several drug targets. Modification of these polypharmacological lead compounds is then needed to generate target-selective compounds. In the work presented here, we aimed at separation of the anti-androgen activity and vitamin D activity of previously identified diphenylpentane lead compounds. Based on the determined X-ray crystal structures of androgen receptor and vitamin D receptor, bulky substituents were introduced at the t-butyl group in the lead compounds 2 and 3. As a result of this structural development, we obtained 16c, which exhibits more potent anti-androgen activity (IC(50): 0.13 mu M) than clinically used anti-androgen bicalutamide (IC(50): 0.67 mu M) with 30-fold selectivity over vitamin D activity. This result indicates that lead compounds obtained via the multi-template approach can indeed be structurally modified to generate target-selective compounds. (C) 2010 Elsevier Ltd. All rights reserved.