1,2-双(4-羟基苯基)-乙酮 | 3669-47-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1,2-双(4-羟基苯基)-乙酮
• 中文别名: 1,2-双(4-羟基苯基)乙酮
• 英文名称: 4,4'-bishydroxydeoxybenzoin
• 英文别名: 4,4′-bishydroxydeoxybenzoin；4,4'-dihydroxy-desoxybenzoin；BHDB；1,2-Bis(4hydroxyphenyl)-ethanone；1,2-Bis(4-hydroxyphenyl)ethanone
• CAS: 3669-47-4
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: HZPYKPXLYFNHFD-UHFFFAOYSA-N

物化性质

• 熔点：
  215–219°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312+P330,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  1,2-双(4-羟基苯基)-乙酮 在 sodium tetrahydroborate 、 对甲苯磺酸 、 zinc(II) iodide 作用下， 以 甲醇 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 21.5h， 生成 N-butyl-N-methyl-8,9-bis(4'-hydroxyphenyl)-7-thianonanamide
  参考文献：
  名称：

  Synthesis and Antiestrogenic Activity of Diaryl Thioether Derivatives

  摘要：

  The reaction of 1,2-diarylethanol and mercapto side chain catalyzed by ZnI2 was used as a key step in the short (three to five steps) and efficient synthesis of 17 diaryl thioether derivatives. Several of these compounds contain a methyl butyl amide chain and an hydroxyaryl moiety, respectively, for antiestrogenic activity and binding affinity on estrogen receptor. No binding affinity for crude cytosolic preparation of the estrogen receptor was observed for compounds without phenolic group, while a low affinity (0.01-0.05%) was measured for mono- or diphenol derivatives. Like the pure steroidal antiestrogen EM-139, these novel nonsteroidal compounds did not exert any stimulatory effect on cell proliferation of (ER(+)) ZR-75-1 human breast cancer cells and partially reversed the amplitude of the stimulatory effect induced by estradiol on this (ER(+)) cell line. No proliferative or antiproliferative effect on (ER(-)) MDA-MB-231 human breast cancer cells was also observed for three of these compounds (39-41). Among the newly synthesized nonsteroidal compounds, the thioether derivative 41 (N-butyl-N-methyl-13,14-bis(4'-hydroxyphenyl)-12-thiatetradecanamide), with a long methylbutylalkanamide side chain and a diphenolic nucleus, was selected as the best antiestrogenic compound. However;this compound was 100-fold less antiestrogenic in (ER(+)) ZR-75-1 cells than the steroidal antiestrogen EM-139.

  DOI：

  10.1021/jm00034a009
• 作为产物：
  描述：

  4,4'-diaminodeoxybenzoin 在 硫酸 作用下， 生成 1,2-双(4-羟基苯基)-乙酮
  参考文献：
  名称：

  Zincke; Fries, Justus Liebigs Annalen der Chemie, 1902, vol. 325, p. 91

  摘要：

  DOI：
• 作为试剂：
  描述：

  脱氧茴香偶姻 、 吡啶盐酸盐 在 1,2-双(4-羟基苯基)-乙酮 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 5.0h， 以to give 38 g (85% yield) of the desired product的产率得到1,2-双(4-羟基苯基)-乙酮
  参考文献：
  名称：

  Deoxybenzoin-derived anti-flammable polymers

  摘要：

  本发明提供了新型阻燃聚合物和材料，以及它们的合成和应用。更具体地说，这些阻燃聚合物是以脱氧苯并酮为基础的聚合物。

  公开号：

  US08314202B2

文献信息

• Structure-activity relationship of estrogens: receptor affinity and estrogen antagonist activity of certain (E)- and (2)-1,2,3-triaryl-2-propen-2-ones
  作者：Shubhra Mittal、Susheel Durani、Randhir S. Kapil

  DOI：10.1021/jm00382a019

  日期：1985.4

  (E)- and (Z)-1,2,3-triphenyl-2-propen-1-ones and some of their phenolic and alkoxy analogues, substituted at the para position in one or more of the aromatic rings, were synthesized and assigned geometry on the basis of their spectroscopic data. The structure-activity relationship of the triarylpropenones was studied from the point of view of their estrogen receptor affinity and estrogen agonist and antagonist activities. (E)- as well as (Z)-propenones were found to compete with estradiol for binding with the mouse uterine cytosol receptors, with phenolic analogues usually more potent than the unsubstituted as well as alkoxypropenones. The (E)-propenones, which have now emerged as a new group of estrogen receptor ligands, were found to differ from Z isomers quite markedly in their binding specificities. The uterotrophic and antiuterotrophic assays in immature mice revealed that while some of the compounds were marginally estrogenic, nearly all the isomeric propenones were antiestrogenic to a varying degree.

  (E)-和(Z)-1,2,3-三苯甲丙二烯酮及其酚类和醚类的类物在芳香环的para位被取代的情况下被合成了，这些化合物的立体结构是基于它们的光谱数据进行判断的。从雌激素受体亲和力以及雌激素亲和力的协同作用和拮抗作用的层面，探讨了丙三环酮的结构活性关系。无论是(E)-还是(Z)-的丙烯酮都与小鼠子宫细胞受体发生了竞争性的结合，酚类的类物通常比未取代的结构和醚类的丙烯酮有更强的亲和力。可以与雌激素结合的丙烯酮的身影作为新的雌激素受体配体逐渐浮现，但它们与(Z)-同分异构体在结合特异性方面有很大的不同。生胎性以及抑生胎性在幼鼠中的测试显示，虽然有些化合物具有微弱的雌激素性质，但几乎所有的同分异构体丙烯酮都具有一定程度的抑生胎性。
• Estrogen receptor modulators
  申请人：——

  公开号：US20030225132A1

  公开（公告）日：2003-12-04

  The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, and cancer, in particular of the breast, uterus and prostate.

  本发明涉及化合物及其衍生物，它们的合成以及它们作为雌激素受体调节剂的用途。本发明的化合物是雌激素受体的配体，因此可能对治疗或预防与雌激素功能相关的多种疾病条件有用，包括：骨质疏松、骨折、骨质疏松症、软骨退化、子宫内膜异位症、子宫肌瘤病、潮热、低密度脂蛋白胆固醇水平升高、心血管疾病、认知功能障碍、脑退行性疾病、再狭窄、男性乳房增大、血管平滑肌细胞增殖、肥胖、尿失禁和癌症，尤其是乳腺、子宫和前列腺癌。
• Diarylacetylenes, enamines and acetylenic polymers and their production
  申请人：——

  公开号：US05233046A1

  公开（公告）日：1993-08-03

  Diarylacetylenes and diarylenamines are synthesized from a Schiff's base and an N-arylmethylheterocycle; these compounds are useful as intermediates for a variety of polymers; in particular an efficient process is provided for producing diaryl acetylenes useful in the efficient production of acetylene group-containing polymers which can be cross-linked to produce high strength polymers free of structural defects such as conventionally arise as a result of liberation of volatiles during the cross-linking.

  从Schiff碱和N-芳基甲基杂环化合物合成二芳基乙炔和二芳基胺；这些化合物可作为各种聚合物的中间体，特别是提供了一种高效的方法来生产二芳基乙炔，用于高效生产含乙炔基团的聚合物，这些聚合物可以交联形成高强度聚合物，不会出现结构缺陷，如传统交联过程中由于挥发物的释放而产生的缺陷。
• HALOGEN-FREE FLAME RETARDING MATERIALS BASED ON BISPHENOL TRIAZOLE RESINS AND POLYMERS
  申请人：Emrick Todd

  公开号：US20120316313A1

  公开（公告）日：2012-12-13

  The invention provides halogen-free, bisphenol triazole resins and polymers having exceptional flame retarding properties, related compositions and methods of making and use thereof.

  这项发明提供了无卤、双酚三唑树脂和聚合物，具有优异的阻燃性能，相关的组合物、制备方法和使用方法。
• [EN] ESTROGEN RECEPTOR MODULATORS<br/>[FR] MODULATEURS DE RECEPTEURS D'OESTROGENE
  申请人：MERCK & CO INC

  公开号：WO2003091239A1

  公开（公告）日：2003-11-06

  The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, and cancer, in particular of the breast, uterus and prostate.

  本发明涉及化合物及其衍生物，它们的合成以及作为雌激素受体调节剂的用途。本发明的化合物是雌激素受体的配体，因此可能用于治疗或预防与雌激素功能相关的各种疾病，包括：骨质疏松、骨折、骨质疏松症、软骨退化、子宫内膜异位症、子宫肌瘤病、潮热、低密度脂蛋白胆固醇水平升高、心血管疾病、认知功能受损、脑退行性疾病、再狭窄、男性乳房发育、血管平滑肌细胞增殖、肥胖、失禁和癌症，尤其是乳腺、子宫和前列腺癌。