4,4'-(二乙基乙二基)二-2,5-环己二烯-1-酮 | 5664-37-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4,4'-(二乙基乙二基)二-2,5-环己二烯-1-酮
• 中文别名: 三环[3.2.1.02,4]辛烷-6-酮,3-(羟甲基)-,(1R,2R,3R,4S,5R)-rel-(9CI)
• 英文名称: DES-4,4'-quinone
• 英文别名: diethylstilbestrol-4’,4’’-quinone；Diethylstilbestrol quinone；4-[4-(4-oxocyclohexa-2,5-dien-1-ylidene)hexan-3-ylidene]cyclohexa-2,5-dien-1-one
• CAS: 5664-37-9
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: LKSFYQFTIVHZAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  己烯雌酚 在 6C₁₆H₁₀O₄^(2-)*6Zr⁽⁴⁺⁾*4O^(2-)*4HO^(1-)*3C₃H₇NO*30H₂O 、 双氧水 、 horseradish peroxidase 作用下， 以 aq. buffer 为溶剂， 生成 4,4'-(二乙基乙二基)二-2,5-环己二烯-1-酮
  参考文献：
  名称：

  酶促金属有机骨架传感系统检测己烯雌酚

  摘要：

  酶辅助MOF传感系统是首次设计用于己烯雌酚的荧光检测。在其中，己烯雌酚被HRP / H 2 O 2特异性氧化为醌形式，并被基于1,2-苯乙烯的发光MOF选择性捕获，以诱导荧光反应。通过酶促反应和MOF吸附的串联过滤，可以实现对分析物的精细结构区分。

  DOI：

  10.1002/chem.201703438

文献信息

• Crystalline Diethylstilbestrol (DES) Quinone: Synthesis, X-ray Analysis, and Stability
  作者：Yusuf J. Abul-Hajj、Katmerka Tabakovic、William H. Ojala、William B. Gleason

  DOI：10.1021/ja00125a028

  日期：1995.5
• Estrogen-Dependent Gene Regulation by an Oxidative Metabolite of Diethylstilbestrol, Diethylstilbestrol-4′,4″-Quinone
  作者：Kun Chae、Jonathan Lindzey、John A McLachlan、Kenneth S Korach

  DOI：10.1016/s0039-128x(97)00158-x

  日期：1998.3

  Diethylstilbestrol (DES) is a well-characterized carcinogen in humans and animals although its mechanisms of carcinogenicity are not yet known. While the estrogenic activity of DES is important, there is evidence that oxidative metabolism also plays an important role for its toxicity. DES is oxidatively metabolized in vivo and in vitro to a number of compounds including diethylstilbestrol-4',4 "-quinone (DQ), an unstable and reactive intermediate, and Z,Z-dienestrol (ZZ-DIEN). Estrogen receptor (ER) binding assays with mouse uterine cytosol indicate that DES, DQ and ZZ-MIEN have relative binding affinities of 286, 3.6 and 0.3, respectively, relative to estradiol as 100. In addition, DQ binds irreversibly and specifically to ER suggesting that DQ may be biologically active despite its rapid metabolism and lower binding affinity compared to DES. To test this, COS-1 cells were transfected with an estrogen responsive reporter construct containing a VitA2 estrogen response element (ERE) with or without an ER expression vector. In the presence of ER, treatments with DES, DQ and ZZ-DIEN resulted in 11, 10, and 2-fold induction of chloramphenicol acetyltransferase (CAT) activity, respectively. This induction was mediated by estrogen receptor since it was suppressed by pretreatment with a 10-fold excess of the pure antiestrogen ICI 182,780. These data indicate that DQ is a biologically active intermediate that is capable of transactivation of estrogen responsive genes through the ER. Furthermore, the data suggest that the ability of DQ to irreversibly bind ER may result in persistent stimulation of ER. This persistent stimulation may be related to the carcinogenicity of DES. (C) 1998 by Elsevier Science Inc.