trans-<4,4'-(diethylvinylen) bis (phenyl)>diacetate | 5965-06-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-<4,4'-(diethylvinylen) bis (phenyl)>diacetate
• 英文别名: trans-diethylstilbesterol diacetate；diethylstilbestrol diacetate；3,4-bis-(4-acetoxy-phenyl)-hex-3t-ene；3,4-Bis-(4-acetoxy-phenyl)-hex-3t-en；4.4'-Diacetoxy-α.α'-diaethyl-trans-stilben；Di-O-acetyl-diethylstilboestrol；[4-[(E)-2-(4-Acetoxyphenyl)-1-ethyl-but-1-enyl]phenyl] acetate；[4-[(E)-4-(4-acetyloxyphenyl)hex-3-en-3-yl]phenyl] acetate
• CAS: 5965-06-0
• 化学式: C₂₂H₂₄O₄
• 分子量: 352.43
• InChiKey: NFCAKXYIMSRNLP-QURGRASLSA-N

物化性质

• 熔点：
  122-124 °C
• 沸点：
  461.8±25.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)
• 保留指数：
  2514

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  trans-<4,4'-(diethylvinylen) bis (phenyl)>diacetate 在 二硫化碳 、 溴 作用下， 生成 3,4-bis-(4-acetoxy-phenyl)-3,4-dibromo-hexane
  参考文献：
  名称：

  Henne; Bruylants, Bulletin des Societes Chimiques Belges, 1948, vol. 57, p. 320,328

  摘要：

  DOI：
• 作为产物：
  描述：

  4-乙酰氧基苯丙酮 在 palladium on activated charcoal 氢气 作用下， 以 丙酮 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 生成 trans-<4,4'-(diethylvinylen) bis (phenyl)>diacetate
  参考文献：
  名称：

  Marson,L.M., Bollettino Chimico Farmaceutico, 1963, vol. 102, p. 317 - 321

  摘要：

  DOI：

文献信息

• Biological Evaluation of Novel Cyclopropyl Analogues of Stilbene, Stilbenediol, and Phenanthrene for Estrogenic and Antiestrogenic Activity
  作者：J.T. Pento、K.K. Koenig、R.A. Magarian、S.D. Kosanke、D.L. Gilliland

  DOI：10.1002/jps.2600770206

  日期：1988.2

  agonist/antagonist activity which may limit their therapeutic effectiveness. This problem of mixed activity led to the synthesis and identification of a cyclopropyl derivative of cis-stilbene which we have named Analog I. This compound (1,1-dichloro-cis-2,3-diphenylcyclopropane) displayed only antiestrogenic activity in the mouse. The present study was designed to evaluate cyclopropyl derivatives of Analog

  已知三苯乙烯型抗雌激素，例如他莫昔芬可用于治疗雌激素依赖性肿瘤。然而，这些化合物显示出混合的雌激素激动剂/拮抗剂活性，这可能限制了它们的治疗效果。这个混合活性的问题导致了顺式-苯乙烯的环丙基衍生物的合成和鉴定，我们将其命名为类似物I。该化合物（1,1-二氯-顺式-2,3-二苯基环丙烷）在小鼠中仅表现出抗雌激素活性。本研究的目的是使用标准的3-d促子宫卵母细胞测定法和子宫细胞质雌激素受体测定法评估类似物II的环丙基衍生物在大鼠中的雌激素和抗雌激素活性。五种化合物（BF），是，烯二醇，在这项研究中评估了菲和菲。其中的三种化合物（BD）在大鼠中既不显示雌激素活性，也不显示抗雌激素活性。E和F的相对雌激素活性在促同卵细胞测定中分别为己烯雌酚的11.3和1.5％，在雌激素受体测定中分别为雌二醇的39％和6.2％。E和F均未在大鼠中显示抗雌激素活性。结果表明，E和F的相对雌激素和受体结合活性与以前在小
• Synthesis of Cyclopropyl Analogs of Stilbene and Stilbenediol as Possible Antiestrogens
  作者：Robert A. Magarian、Eric Joel Benjamin

  DOI：10.1002/jps.2600641007

  日期：1975.10

  Conformationally rigid analogs of stilbene and stilbenediol were prepared via gem-dichlorocyclopropyl precursors utilizing two different synthetic methods: a two-phase catalytic method and an organomercurial method. These precursors were reduced to the corresponding cyclopropyl analogs using sodium and methanol. All compounds are being tested to discriminate between estrogenic and antiestrogenic ability

  通过宝石-二氯环丙基前体，使用两种不同的合成方法：两相催化方法和有机汞方法，制备了和二醇的构象刚性类似物。使用钠和甲醇将这些前体还原为相应的环丙基类似物。测试所有化合物以区分雌激素和抗雌激素能力，确定雌激素结合能力，并评估组织培养物的抗癌活性。
• Carbon-13 nuclear magnetic resonance study of meso-hexestrol and its derivatives.
  作者：TAIKO ODA、TOMOKO MURAI、YOSHIHIRO SATO

  DOI：10.1248/cpb.36.1534

  日期：——

  The carbon-13 unclear magnetic resonance chemical shift assignments for meso-hexestrol (1a), made on the basis of two-dimensional 13-1H chemical shift correlation, long-range selective 1H decoupling experiment, and a reported two-dimensional Fourier-trasform experiment for long-range proton-carbon-13 spin coupling constants, are reported. For measurement of carbon-protoncoupling constants of meso-hyxestrol derivatives (1b-e, 2a-d, 3a-c, and 4), the coupling informaiton was detected by using a gated decoupling facility which permitted retention of the nuclear Overhauser enhancement and a long-range selective 1H decoupling experiment. The results showed that the aromatic carbon resonances are influenced by the structure (no double bond, or one or two double bond(s)) of the hexane framework in the central portion.

  根据二维 13-1H 化学位移相关性、长程选择性 1H 去耦实验和已报道的长程质子-碳-13 自旋耦合常数的二维傅立叶变换实验，报告了中-己烯雌酚（1a）的碳-13 不清晰磁共振化学位移分配。在测量中-己烯雌酚衍生物（1b-e、2a-d、3a-c 和 4）的碳-质子耦合常数时，使用了门控去耦设备检测耦合信息，该设备允许保留核奥弗霍瑟增强和长程选择性 1H 去耦实验。结果表明，芳香碳共振受中央部分己烷框架结构（无双键或一个或两个双键）的影响。
• The biological activities of diethylstilbestrol and its derivatives.
  作者：YOSHIHIKO INAMORI、MAYURI KUBO、MASAFUMI OGAWA、MASAMITSU MORIWAKI、HIROSHI TSUJIBO、KIMIYE BABA、MITSUGI KOZAWA

  DOI：10.1248/cpb.33.4478

  日期：——

  Diethylstilbestol (I), a nonsteroidal estrogen, showed strong coronary vasodilator action on isolated guinea-pig heart, as well as ichthyotoxicity and antimicrobial activity. First, the coronary vasodilator action of I (ED50 : 0.26μg/heart) on isolated guinea-pig heart was much stronger than that of papaverine (ED50 : 7.0μg/heart) used as a standard. On the other hand, the activities of derivatives of I, i. e., I-diphosphate (II), I-dimethyl ether (III), I-diacetate (IV), I-dipropionate (V) and hexestrol (VI) were weaker than that of I. Second, I showed strong ichthyotoxicity (median tolerance limit at 48h : 3.30 ppm in Oryzias latipes and 4.50 ppm in Carassius auratus). On the other hand, the ichthyotoxic activities of II-V were weaker than that of I. However, VI showed the same toxicity as I on both fishes. Third, the antimicrobial activities of II-V were weaker than that of I, whereas that of VI was stronger. In particular, I and VI showed strong antifungal activity against Trichophyton spp. It was concluded that both the hydroxyl groups attached to the benzene rings and the transolefin structure are necessary for coronary vasodilator action, while only the hydroxyl groups attached to the benzene ring are necessary for the ichthyotoxic and antimicrobial activities.

  二乙基芪雌醇（I）是一种非甾体雌激素，对离体豚鼠心脏具有很强的冠状动脉血管扩张作用，同时还具有鱼毒性和抗菌活性。首先，I（ED50：0.26 微克/心）对离体豚鼠心脏的冠状血管扩张作用远强于作为标准的木蝴蝶碱（ED50：7.0 微克/心）。另一方面，I 的衍生物，即 I-二磷酸酯（II）、I-二甲醚（III）、I-二乙酸酯（IV）、I-二丙酸酯（V）和己烯雌酚（VI）的活性均弱于 I。另一方面，II-V 的鱼毒活性比 I 弱，但 VI 对两种鱼类的毒性与 I 相同。第三，II-V 的抗菌活性弱于 I，而 VI 则更强。得出的结论是，苯环上的羟基和反异亮氨酸结构都是冠状血管扩张作用所必需的，而只有苯环上的羟基才是鱼毒和抗菌活性所必需的。
• Process for producing hormones
  申请人：DU PONT

  公开号：US02385853A1

  公开（公告）日：1945-10-02