4-Hydroxy-4-phenyl-1-buten-3-one | 195508-14-6

• 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: 4-Hydroxy-4-phenyl-1-buten-3-one
• 英文别名: 4-hydroxy-4-phenyl-1-butene-3-one；1-Hydroxy-1-phenylbut-3-en-2-one
• CAS: 195508-14-6
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: HYWNLNKGSCTKMU-UHFFFAOYSA-N

物化性质

• 沸点：
  280.9±33.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-4-phenyl-1-buten-3-one 在 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl 、 对甲苯磺酸 作用下， 生成 1-phenyl-3-butene-1,2-dione
  参考文献：
  名称：

  Synthesis of vinyl 1,2-diketones

  摘要：

  A new route is outlined for preparation of vinyl 1,2-diketones via a three-step sequence. First, allylic alcohols are photooxidized by O-2 to hydroperoxides, which are reduced to vinyl 1,2-diols. These vinyl 1,2-diols are oxidized to vinyl 1,2-diketones with oxoammonium salts, which are prepared in situ from organic nitroxyl radicals. The new route is short, avoids the use of protecting groups, and is generally applicable to obtain aliphatic or aromatic vinyl 1,2-diketones. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.03.157
• 作为产物：
  描述：

  2,2-diethoxy-1-phenyl-3-buten-1-ol 在 50percent TFA 作用下， 以 氯仿 为溶剂， 反应 0.17h， 以90%的产率得到4-Hydroxy-4-phenyl-1-buten-3-one
  参考文献：
  名称：

  Reaction of γ,γ-Dialkoxyallylic Zirconium Species with Aldehyde as Protected Acryloyl Anion

  摘要：

  DOI：

  10.1021/jo991107b

文献信息

• 1,5-DIPHENYL-PENTA-1,4-DIEN-3-ONE COMPOUNDS
  申请人：Shih Charles C-Y

  公开号：US20120046247A1

  公开（公告）日：2012-02-23

  This invention relates to compounds of Formula (I), (II), or (III) as shown in the specification, which contain a 1,5-diphenylpenta-1,4-dien-3-one backbone. These compounds can be used to treat cancer, inflammatory disease, or autoimmune disease.

  这项发明涉及到规范中所示的具有Formula (I)、(II)或(III)的化合物，这些化合物含有1,5-二苯基戊-1,4-二烯-3-酮骨架。这些化合物可用于治疗癌症、炎症性疾病或自身免疫疾病。
• TREATMENT OF CANCER, INFLAMMATORY DISEASE, AND AUTOIMMUNE DISEASE
  申请人：AndroScience Corporation

  公开号：US20140371177A1

  公开（公告）日：2014-12-18

  A method of treating cancer, inflammatory disease, and autoimmune disease by administering to a subject in need thereof an effective amount of one or more 1,5-dipenylpenta-1,4-dien-3-one compounds. The compounds feature either or both of the phenyl rings being substituted with hydroxyl, diethyl(2-alkoxyethyl)amine, 1-(2-alkoxyethyl)piperidine, sulfonate, phosphinate, or phosphate.

  一种通过向需要治疗癌症、炎症性疾病和自身免疫疾病的受试者施用一种或多种1,5-二苯基戊-1,4-二烯-3-酮化合物的有效量来治疗的方法。这些化合物的特点是苯环之一或两个都被羟基、二乙基(2-烷氧基乙基)胺、1-(2-烷氧基乙基)哌啶、磺酸盐、磷酸盐或亚磷酸盐取代。
• Stereoselective synthesis of 3(2H)-dihydrofuranones by addition of lithiated methoxyallene to chiral aldehydes
  作者：Stephan Hormuth、Hans Ulrich Reissig

  DOI：10.1021/jo00080a013

  日期：1994.1

  Lithiated methoxyallene 2 adds to chiral aldehydes such as 5-phenylpropanal and N,N-dibenzylated alpha-amino aldehydes 4-8 to give products 9-14 in good yields and with excellent anti-selectivity. The stereochemical outcome of these reactions can be explained by the Felkin-Anh model in a straightforward manner. The crude reaction products can either be transformed to enones by hydrolysis with acid or be converted into 2,5-dihydro-3-methoxyfuran derivatives 19-24 by treatment with potassium tert-butoxide in DMSO. The latter can be hydrolyzed to give 3(2H)-dihydrofuranones 25-29. The diastereoselectivity of the initial addition step is transferred to the dihydrofuran derivative without a major change in the isomer ratio. Compounds derived from alpha-amino aldehydes 5, 6, and 8 are assumed to be enantiomerically pure. Sodium borohydride reductions of and Grignard additions to 3(2H)-dihydrofuranones 27a and 28a demonstrate that these chiral ketones react in a highly diastereoselective manner. In summary, this paper shows that lithiated methoxyallene 2 can serve as a very useful equivalent for alpha,beta-unsaturated acyl anions and 1,3-dipolar synthons in asymmetric synthesis.
• US8822732B2
  申请人：——

  公开号：US8822732B2

  公开（公告）日：2014-09-02
• US9359279B2
  申请人：——

  公开号：US9359279B2

  公开（公告）日：2016-06-07