1-hydroxy-1-(2-hydroxyphenyl)-5-phenylpenta-1,4-dien-3-one | 205308-02-7

• 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: 1-hydroxy-1-(2-hydroxyphenyl)-5-phenylpenta-1,4-dien-3-one
• 英文别名: (E)-1-(2-hydroxyphenyl)-5-phenylpent-4-ene-1,3-dione
• CAS: 205308-02-7
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: NQLCKTLOSJVDJM-SEBJLUHNSA-N

物化性质

• 沸点：
  464.3±45.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-hydroxy-1-(2-hydroxyphenyl)-5-phenylpenta-1,4-dien-3-one 在 phenyltrimethylammonium tribromide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以67%的产率得到(E)-3-bromo-2-(2-phenylvinyl)-4H-chromen-4-one
  参考文献：
  名称：

  合成羟基化 2,3-二芳基氧杂蒽的新途径

  摘要：

  描述了一种合成羟基化 2,3-二芳基氧杂蒽酮的新型、有效和通用的路线。该合成的关键中间体 3-Bromo-2-styrylchromone 是通过适当的 2'-肉桂酰氧基苯乙酮的 Baker-Venkataraman 重排，然后与苯-基三甲基三溴化铵进行一锅反应获得的。这些溴色酮与取代苯乙烯的 Heck 反应生成甲氧基化的 2,3-二芳基氧杂蒽酮。用 BBr 3 裂解甲基得到所需的羟基化 2,3-二芳基氧杂蒽酮。

  DOI：

  10.1055/s-2007-990900
• 作为产物：
  描述：

  2-acetylphenyl (E)-3-phenylacrylate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到1-hydroxy-1-(2-hydroxyphenyl)-5-phenylpenta-1,4-dien-3-one
  参考文献：
  名称：

  2-苯乙烯基色酮与重氮甲烷的1,3-偶极环加成反应合成4-芳基-3-（2-苯甲酰基）-2-吡唑啉

  摘要：

  首次报道的2-苯乙烯基色酮与重氮甲烷的1，3-偶极环加成反应得到4-芳基-3-（2-苯甲酰基）-2-吡唑啉。然而，还发现3-芳基-4-（2-苯甲酰基）-1-吡唑啉是该反应的次要产物。这两个系列的吡唑啉已得到充分表征。

  DOI：

  10.1002/jhet.5570350140

文献信息

• Efficient Syntheses of New Polyhydroxylated 2,3-Diaryl-9<i>H</i>-xanthen-9-ones
  作者：Clementina M. M. Santos、Artur M. S. Silva、José A. S. Cavaleiro

  DOI：10.1002/ejoc.200900026

  日期：2009.6

  between 3-bromo-2-methyl-4H-chromen-4-one and benzaldehydes, or through Baker–Venkataraman rearrangements of 2-acetylphenyl cinnamates, followed by one-pot bromination/cyclisation with phenyltrimethylammonium tribromide. The 2,3-diaryl-9H-xanthene-9-ones were obtained in one-pot transformations involving Heck reactions between (E)-3-bromo-2-styryl-4H-chromen-4-ones and styrenes, followed by electrocyclisation

  已经通过两种不同的方法合成了大量羟基化的 2,3-二芳基-9H-xanthen-9-ones，从 3-bromo-2-methyl-4H-chromen-4-one 或 (E)- 3-bromo-2-styryl-4H-chromen-4-ones。前一种方法涉及 3-bromo-2-methyl-4H-chromen-4-one 和苯乙烯之间的 Heck 反应，导致 (E)-2-methyl-3-styryl-4H-chromen-4-ones; 这些与苯甲醛缩合得到 (E,E)-2,3-distyryl-4H-chromen-4-ones，这导致所需的 2,3-diaryl-9H-xanthen-9-ones 在 1,2 中回流,4-三氯苯。3-Bromo-2-styryl-4H-chromen-4-ones 是通过 3-bromo-2-methyl-4H-chromen-4-one 和苯甲醛之间的羟醛缩合获得的，或者通过
• The synthesis of various cycloalkana[d ]xanthones and conversion of the cyclohexa-analogue to a 7,7a-dimethylcyclohexa[d ]xanthene †
  作者：Roy M. Letcher、Tai-Yuen Yue、Kwei-Fung Chiu、Avijit S. Kelkar、Kung-Kai Cheung

  DOI：10.1039/a804365e

  日期：——

  The synthesis of cyclo-penta-, -hexa- and -hepta-[d]xanthones 5 from (E)-(2-hydroxyphenyl)-5-arylpent-4-ene-1,3-diones 4, cycloalkanones and pyrrolidine is described. Reactions to modify 5 in an attempt to synthesize analogues of the five naturally occurring cyclohexa[d]xanthenes (with general formula 1) are also described: these reactions include C-methylations at C-7 and C-7a, hydride reduction of the 8-keto group, dehydroxylations and finally catalytic reduction to give 16. The stereochemistry of 16 established by NOE and an X-ray crystal structure of 9aB differs from 1 at two contiguous C-atoms.

  本文描述了从(E)-(2-羟基苯基)-5-芳基戊-4-烯-1,3-二酮 4、环烷酮和吡咯烷合成环五、六和七-[d]氧杂蒽酮 5 的过程。此外，还描述了对 5 进行改性以试图合成五种天然环己基[d]氧杂蒽类似物（通式 1）的反应：这些反应包括 C-7 和 C-7a 的 C-甲基化、8-酮基的氢化物还原、脱羟基，最后通过催化还原得到 16。通过 NOE 和 9aB 的 X 射线晶体结构确定的 16 的立体化学结构在两个连续的 C 原子上与 1 不同。
• CHROMENONE DERIVATIVES AS TRPV3 ANTAGONISTS
  申请人：Chaudhari Sachin Sundarlal

  公开号：US20110237659A1

  公开（公告）日：2011-09-29

  The present invention provides transient receptor potential vanilloid (TRPV) modulators of formula (I). In particular, compounds described herein are useful for treating or preventing diseases, conditions and/or disorders modulated by TRPV3. Also provided herein are processes for preparing compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and/or disorders modulated by TRPV3.

  本发明提供了公式（I）的瞬时受体电位香草酰基（TRPV）调节剂。特别地，本文所描述的化合物可用于治疗或预防TRPV3调节的疾病、状况和/或障碍。本文还提供了用于制备所述化合物的过程、用于其合成的中间体、制药组合物以及用于治疗或预防TRPV3调节的疾病、状况和/或障碍的方法。
• Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones
  作者：David S. Clarke、Christopher D. Gabbutt、John D. Hepworth、B. Mark Heron

  DOI：10.1016/j.tetlet.2005.06.058

  日期：2005.8

  3-Acylchromones and 3-acylflavones, readily available by acylation of 2'-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones. (c) 2005 Elsevier Ltd. All rights reserved.
• 1,5-Diphenylpenta-2,4-dien-1-ones as potent and selective monoamine oxidase-B inhibitors
  作者：Nicoletta Desideri、Rossella Fioravanti、Luca Proietti Monaco、Mariangela Biava、Matilde Yáñez、Francesco Ortuso、Stefano Alcaro

  DOI：10.1016/j.ejmech.2012.11.006

  日期：2013.1

  A series of (2E,4E)-1-(2-hydroxyphenyl)-5-phenylpenta-2,4-dien-1-ones (3a-r) and (2Z,4E)-3-hydroxy-1-(2-hydroxyphenyl)-5-phenylpenta-2,4-dien-1-ones (6a-l) were synthesized and evaluated in vitro as inhibitors of the two human Monoamine oxidase (hMAO) isoforms, MAO-A and MAO-B. Most of the compounds showed a selective MAO-B inhibitory activity in the nanomolar or low micromolar range. (2E,4E)-5-(4-Chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)penta-2,4-dien-1-one (3g) and (2E,4E)-5-(4-chlorophenyl)-1-(2,4-dihydroxyphenyl)penta-2,4-dien-1-one (3h) were the most potent hMAO-B inhibitors exhibiting IC50 of 4.51 nM and 1135 nM, respectively, coupled with high selectivity. Moreover, partial recovery of MAO-B activity was observed after repeated washing in the presence of isatin (reversible inhibitor) and compounds 3g and 3h suggesting a reversible inhibition of the enzyme. Molecular mechanics and quantum chemistry methods were used to elucidate the MAO recognition of the most active inhibitors 3g and 3h. (C) 2012 Elsevier Masson SAS. All rights reserved.