(E)-4-(3-ethoxy-2-hydroxyphenyl)but-3-en-2-one | 22214-36-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-(3-ethoxy-2-hydroxyphenyl)but-3-en-2-one
• 英文别名: trans-o-Bourbonyliden-aceton；4-(3-Ethoxy-2-hydroxyphenyl)but-3-en-2-one
• CAS: 22214-36-4
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: IGRSFPPCXLTNII-BQYQJAHWSA-N

物化性质

• 熔点：
  77-78 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  361.5±27.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-(3-ethoxy-2-hydroxyphenyl)but-3-en-2-one 在 吡啶 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 、 mineral oil 为溶剂， 反应 55.0h， 生成 (E)-2-ethoxy-6-(5-hydroxy-3-methylpent-3-enyl)phenol
  参考文献：
  名称：

  金催化的游离醇不对称烯丙基取代：对映体的手性铬与季立体中心合成维生素E及其类似物的对映选择性方法。

  摘要：

  α-和γ-生育酚（维生素E家族中最具生物活性的成员）及其类似物的对映选择性合成是采用新的对映选择性金催化的分子内烯丙基烷基化反应，然后进行烯烃交叉复分解作为关键步骤而完成的。事实证明该方法适用于不同的烯烃，突出了其在合成各种文库中的潜力。

  DOI：

  10.1002/chem.201403768
• 作为产物：
  描述：

  3-乙氧基水杨醛 、 丙酮 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 48.0h， 生成 (E)-4-(3-ethoxy-2-hydroxyphenyl)but-3-en-2-one
  参考文献：
  名称：

  金催化的游离醇不对称烯丙基取代：对映体的手性铬与季立体中心合成维生素E及其类似物的对映选择性方法。

  摘要：

  α-和γ-生育酚（维生素E家族中最具生物活性的成员）及其类似物的对映选择性合成是采用新的对映选择性金催化的分子内烯丙基烷基化反应，然后进行烯烃交叉复分解作为关键步骤而完成的。事实证明该方法适用于不同的烯烃，突出了其在合成各种文库中的潜力。

  DOI：

  10.1002/chem.201403768

文献信息

• 3,4,5,6-Tetrahydro-2,6-methano-4 beta-amino-1-benzoxocin derivatives, process for their preparation and compositions containing them
  申请人：GLAXO GROUP LIMITED

  公开号：EP0024843A1

  公开（公告）日：1981-03-11

  Compounds are disclosed of general formula wherein R1 represents a hydrogen atom or C1-4 alkyl or C2-4 alkenyl group, or the group COANH2, CSANH2, or COANHCOCH2NH2 in which A is methylene optionally substituted by a C1-3 alkyl group; and R2 represents a hydrogen atom or a C1-4 alkyl group; or NR1R2 forms a piperidino, piperazino or N-methylpiperazino group; R3 represents a C1-4 alkyl group or a benzyl group; R4 represents a hydrogen or halogen atom; and R5 represents a hydrogen atom or a C1-4 alkyl or C1-4 alkoxy group, with the proviso that one of R4 and Rs is a hydrogen atom and physiologically acceptable salts and bioprecursors thereof. The compounds exert efforts on the central nervous system and, in particular exhibit anxiolytic and anti-convulsant activity. The compounds may be formulated with pharmaceutically acceptable carriers or diluents for administration in conventional manner.

  公开了通式如下的化合物 式中 R1代表氢原子或C1-4烷基或C2-4烯基，或基团COANH2、CSANH2或COANHCOCH2NH2，其中A是可选被C1-3烷基取代的亚甲基；R2代表氢原子或C1-4烷基；或NR1R2形成哌啶基、哌嗪基或N-甲基哌嗪基； R3 代表 C1-4 烷基或苄基； R4 代表氢原子或卤素原子；以及 R5 代表氢原子或 C1-4 烷基或 C1-4 烷氧基，但 R4 和 Rs 之一为氢原子，以及其生理上可接受的盐和生物前体。 这些化合物可作用于中枢神经系统，尤其具有抗焦虑和抗惊厥活性。这些化合物可与药学上可接受的载体或稀释剂一起配制，以常规方式给药。
• Dehydrozingerone, Chalcone, and Isoeugenol Analogues as in Vitro Anticancer Agents
  作者：Jin Tatsuzaki、Kenneth F. Bastow、Kyoko Nakagawa-Goto、Seiko Nakamura、Hideji Itokawa、Kuo-Hsiung Lee

  DOI：10.1021/np060252z

  日期：2006.10.1

  Twenty-eight compounds related to dehydrozingerone ( 1), isoeugenol ( 3), and 2-hydroxychalcone ( 4) were synthesized and evaluated in vitro against human tumor cell replication. Except for isoeugenol analogues 27-35, most compounds exhibited moderate or strong cytotoxic activity against KB, KB-VCR ( a multidrug-resistant derivative), and A549 cell lines. In particular, chalcone 15 showed significant cytotoxic activity against the A549 cell line with an IC50 value of 0.6 mu g/mL. Furthermore, dehydrozingerone analogue 11 and chalcones 16 and 17 showed significant and similar cytotoxic activity against both KB (IC50 values of 2.0, 1.0, and 2.0 mu g/mL, respectively) and KB-VCR (IC50 values of 1.9, 1.0, and 2.0 mu g/mL, respectively) cells, suggesting that they are not substrates for the P-glycoprotein drug efflux pump.
• Anti-tumor agents 255: Novel glycyrrhetinic acid–dehydrozingerone conjugates as cytotoxic agents
  作者：Jin Tatsuzaki、Masahiko Taniguchi、Kenneth F. Bastow、Kyoko Nakagawa-Goto、Susan L. Morris-Natschke、Hideji Itokawa、Kimiye Baba、Kuo-Hsiung Lee

  DOI：10.1016/j.bmc.2007.06.027

  日期：2007.9

  Esterification of glycyrrhetinic acid (GA) with dehydrozingerone (DZ) resulted in a novel cytotoxic GA-DZ conjugate. Based on this exciting finding, we conjugated eleven different DZ analogs with GA or other triterpenoids, including oleanoic acid (OA) or Ursolic acid UA). In an in vitro anti-cancer assay using nine different human tumor cell lines, most of the GA-DZ conjugates showed significant potency. Particularly, compounds 5, 29, and 30 showed significant cytotoxic effects against LN-Cap, 1 A9, and KB cells with ED50 values of 0.6, 0.8, and 0.9 mu M, respectively. Similar conjugates between DZ and OA or UA were inactive suggesting that the GA component is critical for activity. Notably, although GA-DZ conjugates showed potent cytotoxic activity, the individual components (GA and DZ analogs) were inactive. Thus, GA-DZ conjugates are new chemical entities and represent interesting hits for anti-cancer drug discovery and development. (c) 2007 Elsevier Ltd. All rights reserved.
• US4315006A
  申请人：——

  公开号：US4315006A

  公开（公告）日：1982-02-09
• Gold‐Catalyzed Asymmetric Allylic Substitution of Free Alcohols: An Enantioselective Approach to Chiral Chromans with Quaternary Stereocenters for the Synthesis of Vitamin E and Analogues
  作者：Uxue Uria、Carlos Vila、Ming‐Yuan Lin、Magnus Rueping

  DOI：10.1002/chem.201403768

  日期：2014.10.20

  synthesis of α‐ and γ‐tocopherol (the most biologically active members of vitamin E family) and analogues has been accomplished employing a new enantioselective gold catalyzed intramolecular allylic alkylation reaction followed by an olefin cross‐metathesis as key steps. The methodology proved to be applicable to different olefins highlighting its potential for the synthesis of diverse libraries.

  α-和γ-生育酚（维生素E家族中最具生物活性的成员）及其类似物的对映选择性合成是采用新的对映选择性金催化的分子内烯丙基烷基化反应，然后进行烯烃交叉复分解作为关键步骤而完成的。事实证明该方法适用于不同的烯烃，突出了其在合成各种文库中的潜力。