1,5-bis-benzo[1,3]dioxol-5-yl-penta-1,4-dien-3-one | 614-66-4

• 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: 1,5-bis-benzo[1,3]dioxol-5-yl-penta-1,4-dien-3-one
• 英文别名: 1,5-Bis-benzo[1,3]dioxol-5-yl-penta-1,4-dien-3-on；Bis-(3.4-methylendioxy-styryl)-keton；Dipiperonylidenaceton；1,5-bis(1,3-benzodioxol-5-yl)penta-1,4-dien-3-one
• CAS: 614-66-4
• 化学式: C₁₉H₁₄O₅
• mdl: MFCD00047281
• 分子量: 322.317
• InChiKey: UHDVKUQJNWLHLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,5-bis-benzo[1,3]dioxol-5-yl-penta-1,4-dien-3-one 在 硝酸 、 溶剂黄146 作用下， 生成 1,5-bis-(6-nitro-benzo[1,3]dioxol-5-yl)-penta-1,4-dien-3-one
  参考文献：
  名称：

  Haber, Chemische Berichte, 1891, vol. 24, p. 625

  摘要：

  DOI：
• 作为产物：
  描述：

  胡椒醛 在 sodium hydroxide 作用下， 生成 1,5-bis-benzo[1,3]dioxol-5-yl-penta-1,4-dien-3-one
  参考文献：
  名称：

  Faillebin, Annales de Chimie (Cachan, France), 1925, vol. <10> 4, p. 423,435

  摘要：

  DOI：

文献信息

• BIS(ARYLMETHYLIDENE)ACETONE COMPOUND, ANTI-CANCER AGENT, CARCINOGENESIS-PREVENTIVE AGENT, INHIBITOR OF EXPRESSION OF Ki-Ras, ErbB2, c-Myc AND CYCLINE D1, BETA-CATENIN-DEGRADING AGENT, AND p53 EXPRESSION ENHANCER
  申请人：Shibata Hiroyuki

  公开号：US20100152493A1

  公开（公告）日：2010-06-17

  It has been demanded to improve the poor solubility of curcumin to develop an anti-tumor compound capable of inhibiting the growth of various cancer cells at a low concentration. Thus, disclosed is a novel synthetic compound, a bis(arylmethylidene)acetone, which has both of an excellent anti-tumor activity and a chemo-preventive activity. A bis(arylmethylidene)acetone (i.e., a derivative having a curcumin skeleton) which is an anti-tumor compound and has a chemo-preventive activity is synthesized and screened. A derivative having enhanced anti-tumor activity and chemo-preventive activity can be synthesized.

  要改善姜黄素的溶解度，以开发一种能够在低浓度下抑制各种癌细胞生长的抗肿瘤化合物。因此，披露了一种新型合成化合物，双(芳基甲基亚乙酮)，具有优异的抗肿瘤活性和化学预防活性。合成并筛选了一种双(芳基甲基亚乙酮)（即具有姜黄素骨架的衍生物），它是一种抗肿瘤化合物并具有化学预防活性。可以合成具有增强抗肿瘤活性和化学预防活性的衍生物。
• Synthesis of 2-(1,5-diaryl-1,4-pentadien-3-ylidene)-hydrazinecarboximidamide hydrochloride catalyzed by p-dodecylbenzenesulfonic acid in aqueous media under ultrasound irradiation
  作者：Ji-Tai Li、Chao Du、Xiao-Ya Xu、Guo-Fen Chen

  DOI：10.1016/j.ultsonch.2012.02.009

  日期：2012.9

  precursors in synthesis of many natural products and drug molecules. The use of ultrasound, p-dodecylbenzenesulfonic acid (DBSA) and water as solvent improved the synthesis of different 2-(1,5-diaryl-1,4-pentadien-3-ylidene)-hydrazinecarboximidamide hydrochlorides. The best reaction conditions for the condensation of 1,5-diphenyl-1,4-pentadien-3-one with aminoguanidine hydrochloride were as follows:

  mid胺化合物是非常重要的合成中间体，可以作为许多天然产物和药物分子合成中的通用前体。超声，对十二烷基苯磺酸（DBSA）和水作为溶剂的使用改善了不同的2-（1,5-二芳基-1,4-戊二烯-3-亚烷基）-肼基羧酰亚胺酰胺盐酸盐的合成。1,5-二苯基-1,4-戊二烯-3-酮与氨基胍盐酸盐缩合的最佳反应条件如下：1,5-二苯基-1,4-戊二烯-3-酮（1，1 mmol ），氨基胍盐酸盐（1.1 mmol），DBSA（0.5 mmol），水10 mL，反应温度25-27°C，照射频率25 kHz。在2小时内以94％的收率获得2a。在相同条件下，在2-3h内以84-94％的收率获得了其他七个seven基hydr。
• An efficient catalyst free synthesis of nitrogen containing spiro heterocycles via [5 + 1] double Michael addition reaction
  作者：Komal Aggarwal、Kanika Vij、Jitender M. Khurana

  DOI：10.1039/c4ra00521j

  日期：——

  2,4-Diazaspiro[5.5]undecane-1,3,5,9-tetraones and 3-thioxo-2,4-diazaspiro[5.5]undecane-1,5,9-triones have been synthesized via double Michael addition of 1,5-diaryl-1,4-pentadien-3-one with active methylene compounds such as N,N-dimethyl barbituric acid, barbituric acid, thio-barbituric acid and N,N-diphenyl thiobarbituric acid in ethylene glycol at 100 °C in the absence of any catalyst to give high yields within a short reaction time. The structure has been confirmed by X-ray analysis. The single-crystal structure of the diazaspiro compound revealed that the CAr–H⋯π, π–π stacking and intermolecular hydrogen bonding interactions act as major driving forces for crystal packing.

  通过1,5-二芳基-1,4-戊二烯-3-酮与活性甲烷化合物（如N,N-二甲基巴比妥酸、巴比妥酸、硫代巴比妥酸和N,N-二苯基硫代巴比妥酸）在100°C的无催化剂乙二醇中进行双迈克尔加成反应，合成了一系列2,4-二氮杂螺[5.5]十一烷-1,3,5,9-四酮和3-硫代-2,4-二氮杂螺[5.5]十一烷-1,5,9-三酮，产率高且反应时间短。结构通过X射线分析得到确认。二氮杂螺化合物的单晶结构揭示，CAr–H⋯π、π–π堆积和分子间氢键相互作用是晶体堆积的主要驱动力。
• Direct Stereoselective Synthesis of 1-Amino-2,5-diarylcyclohexanecarboxylic Acid Derivatives Based on a [5+1] Annulation of Divinyl Ketone and Isocyanoacetate
  作者：Xianxiu Xu、Qun Liu、Dawei Zhang、Jing Tan

  DOI：10.1055/s-0029-1219537

  日期：2010.4

  A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed stereoselective [5+1] annulation of divinyl ketones and isocyanoacetate was disclosed, which provided a facile and efficient route to 1-amino-2,5-diarylcyclohexanecarboxylic acids as novel constrained cyclohexane analogues of phenylalanine.

  公开了一种 1,8-二氮杂双环[5.4.0]十一碳-7-烯 (DBU)-催化的二乙烯基酮和异氰基乙酸酯的立体选择性 [5+1] 环化，它为 1-氨基-2 的制备提供了一种简便有效的途径， 5-二芳基环己烷羧酸作为苯丙氨酸的新型受限环己烷类似物。
• Sammour,A. et al., Journal fur praktische Chemie (Leipzig 1954), 1973, vol. 315, p. 193 - 201
  作者：Sammour,A. et al.

  DOI：——

  日期：——