(3E,5E)-2-oxo-6-phenylhexa-3,5-dienoic acid | 4403-24-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (3E,5E)-2-oxo-6-phenylhexa-3,5-dienoic acid
• 英文别名: 2-oxo-6-phenyl-3,5-hexadienoic acid；Cinnamylidenepyruvic Acid；2-oxo-6-phenyl-hexa-3,5-dienoic acid；2-Oxo-6-phenyl-hexa-3,5-diensaeure；α-Oxo-ε-phenyl-β.δ-pentadien-α-carbonsaeure；Cinnamalbrenztraubensaeure；2-Oxo-6-phenylhexa-3,5-dienoic acid
• CAS: 4403-24-1
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: HXBHTZSDWPPLKO-KBXRYBNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3E,5E)-2-oxo-6-phenylhexa-3,5-dienoic acid 在 3H₃N*H₃O₄P*12O₃W sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.33h， 生成 isopropyl (3E,5E)-2-hydroxy-6-phenylhexa-3,5-dienoate
  参考文献：
  名称：

  Preparation of optically pure (3E,5E)-alkyl-2-hydroxy-6-arylhexa-3,5-dienoates by Candida parapsilosis ATCC 7330 mediated deracemisation of the racemates

  摘要：

  Biocatalytic deracemisation of a range of racemic (3E,5E)-alkyl-2-hydroxy-6-arylhexa-3,5-dienoates using Candida parapsilosis ATCC 7330 resulted in pure (S)-enantiomers in yields of up to 80% and ee > 99%. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.099
• 作为产物：
  描述：

  丙酮酸 生成 (3E,5E)-2-oxo-6-phenylhexa-3,5-dienoic acid
  参考文献：
  名称：

  Lubrzynska; Smedley, Biochemical Journal, 1913, vol. 7, p. 377

  摘要：

  DOI：

文献信息

• Polyfunctional ()-2-hydroxycarboxylic acids by reduction of 2-oxo acids with hydrogen gas or formate and resting cells of proteus vulgaris
  作者：Anita Schummer、Hongtao Yu、Helmut Simon

  DOI：10.1016/s0040-4020(01)86506-6

  日期：1991.11

  Various ()-2-hydroxy acids such as ()-2-hydroxy-3-enoic-, 3,5-dienoic-, 4-oxo-, ()-3-hydroxy and some others were prepared on a scale up to 0.12 mol by biocatalytic reduction of the corresponding 2-oxo acids with P. vulgaris and hydrogen gas and/or formate as electron donors. With the exception of the 2-hydroxy-4-oxo acids it could be proved that the enantiomeric excess is > 97%. For the 4-oxo derivatives

  各种（）-2-羟基酸如（）-2-羟基-3-烯酸，3,5-二烯酸，4-氧代，（）-3-羟基等，其制备规模可达到通过以寻常的毕赤酵母和氢气和/或甲酸作为电子给体，对相应的2-氧代酸进行生物催化还原，可得到0.12摩尔。除2-羟基-4-氧代酸外，可以证明对映体过量> 97％。对于4-氧代衍生物，可以假定该对映体过量。分离出的产物的产率很高，因为它们是从相当少量的生物催化剂中分离出来的，并且缓冲液的浓度很低，获得的产物浓度在0.1–0.24 M的范围内。在15–20小时内形成1 mmol的产品，约20–40 mg（干重）寻常型毕赤酵母 单元格是必需的。
• Arylidenepyruvic Acid Thiosemicarbazone and Thiazoline Derivatives As Potential Antimicrobial Agents
  作者：A.-Mohsen M. E.Omar、Ibrahim M. Labouta、M. Gabr Kasem、J. Bourdais

  DOI：10.1002/jps.2600721034

  日期：1983.10

  Two novel series of arylidenepyruvic acid thiosemicarbazone and thiazoline derivatives were synthesized and evaluated as potential antimicrobial agents. These substances did not exhibit any significant antibacterial effects when tested against a variety of microorganisms.

  合成了两个新系列的亚芳基丙酮酸硫代半碳酰胺和噻唑啉衍生物，并将其作为潜在的抗菌剂进行了评估。当针对多种微生物进行测试时，这些物质没有表现出任何明显的抗菌作用。
• Histone deacetylase inhibitors
  申请人：CircaGen Pharmaceutical, a Delaware corporation

  公开号：US20020143037A1

  公开（公告）日：2002-10-03

  Histone deacetylase is a metallo-enzyme with zinc at the active site. Compounds having a zinc-binding moiety, such as, for example, a carboxylic acid group, can inhibit histone deacetylase. Histone deacetylase inhibition can repress gene expression, including expression of genes related to tumor suppression. Accordingly, inhibition of histone deacetylase can provide an alternate route for treating cancer, hematological disorders, e.g., hemoglobinopathies, and genetic related metabolic disorders, e.g., cystic fibrosis and adrenoleukodystrophy.

  组蛋白去乙酰化酶是一种在活性位点含锌的金属酶。具有锌结合基团的化合物，例如，羧酸基团，可以抑制组蛋白去乙酰化酶。组蛋白去乙酰化酶的抑制可以抑制基因表达，包括与肿瘤抑制相关的基因的表达。因此，抑制组蛋白去乙酰化酶可以提供治疗癌症、血液学疾病（例如血红蛋白病）以及遗传相关代谢性疾病（例如囊性纤维化和肾上腺白质脑病）的另一途径。
• Catalytic Enantioselective Inverse Electron Demand Hetero-Diels-Alder Reaction with Allylsilanes
  作者：Yuki Matsumura、Takahiro Suzuki、Akira Sakakura、Kazuaki Ishihara

  DOI：10.1002/anie.201402934

  日期：2014.6.10

  The first diastereo‐ and enantioselective inverse electron demand hetero‐Diels–Alder reaction of β,γ‐unsaturated α‐ketoesters with allylsilanes is described. Chiral copper(II) catalysts successfully activate the β,γ‐unsaturated α‐ketoesters and promote the reaction with allylsilanes with excellent enantioselectivities. This process represents a new entry to chiral oxanes.

  描述了β，γ-不饱和α-酮酸酯与烯丙基硅烷的第一个非对映和对映选择性逆电子需求异Diels-Alder反应。手性铜（II）催化剂成功活化了β，γ-不饱和α-酮酸酯，并以优异的对映选择性促进了与烯丙基硅烷的反应。该过程代表了手性恶烷的新进入。
• Histone Deacetylase Inhibitors
  申请人：Lan-Hargest Hsuan-Yin

  公开号：US20120035257A1

  公开（公告）日：2012-02-09

  Histone deacetylase is a metallo-enzyme with zinc at the active site. Compounds having a zinc-binding moiety, such as, for example, a hydroxamic acid group or a carboxylic acid group, can inhibit histone deacetylase. Histone deacetylase can repress gene expression, including expression of genes related to tumor suppression. Accordingly, inhibition of histone deacetylase can provide an alternate route for treating cancer, hematological disorders, e.g., hemoglobinopathies, and genetic related metabolic disorders, e.g., cystic fibrosis and adrenoleukodystrophy.

  组蛋白去乙酰化酶是一种含有锌活性位点的金属酶。具有锌结合基团（例如羟肟酸基团或羧酸基团）的化合物可以抑制组蛋白去乙酰化酶。组蛋白去乙酰化酶可以抑制基因表达，包括与肿瘤抑制相关的基因表达。因此，抑制组蛋白去乙酰化酶可以提供一种替代途径来治疗癌症、血液疾病（例如血红蛋白病）和遗传相关代谢疾病（例如囊性纤维化和肾上腺白质营养不良症）。