(E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one | 144850-45-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one
• 英文别名: (E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-one；(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-one；1t-benzo[1,3]dioxol-5-yl-4,4-dimethyl-pent-1-en-3-one；1-benzo[1,3]dioxol-5-yl-4,4-dimethyl-pent-1-en-3-one；(E)-4,4-dimethyl-1-[(3,4-methylenedioxy)-phenyl]-1-penten-3-one；(E)-1-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethylpent-1-en-3-one；1t-Benzo[1,3]dioxol-5-yl-4,4-dimethyl-pent-1-en-3-on；1-(1,3-benzodioxol-5-yl)-4,4-dimethyl-1-penten-3-one；1-Benzo[1,3]dioxol-5-yl-4,4-dimethyl-pent-1-en-3-on
• CAS: 144850-45-3
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: LXFNQCGNCFRKRR-FNORWQNLSA-N

物化性质

• 熔点：
  93-94 °C(Solv: ethanol (64-17-5))
• 沸点：
  358.8±11.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)
• LogP：
  3.65 at 21℃ and pH7

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 (+/-)-[5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazol-1-yl](4-methylphenyl)methanone
  参考文献：
  名称：

  Design and synthesis of novel stiripentol analogues as potential anticonvulsants

  摘要：

  A series of stiripentol (SIP) analogues namely, 2-1(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(aryl/H)hydrazinecarboxamides 7a-h, (+/-)-(5RS)-N-(aryl/H)-(1,3-benzodioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazole-1-carboxamides (+/-)-8a-h, and (+/-)-[(5RS)-(1,3-benzodioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazol-1-yl](aryl)methanones (+/-)-13a-f was synthesized by adopting appropriate synthetic routes and was pharmacologically evaluated in the preliminary anticonvulsant screens. The selected bioactive new chemical entities were subjected to ED50 determination and neurotoxicity evaluation. The most active congeners are 7h in MES screen and (+/-)-13b in scPTZ screen which displayed ED50 values of 87 and 110 mg/kg, respectively, as compared to that of STP (ED50 = 277.7 and 115 mg/kg in MES and scPTZ, respectively). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.004
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 (E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one
  参考文献：
  名称：

  Design and synthesis of novel stiripentol analogues as potential anticonvulsants

  摘要：

  A series of stiripentol (SIP) analogues namely, 2-1(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(aryl/H)hydrazinecarboxamides 7a-h, (+/-)-(5RS)-N-(aryl/H)-(1,3-benzodioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazole-1-carboxamides (+/-)-8a-h, and (+/-)-[(5RS)-(1,3-benzodioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazol-1-yl](aryl)methanones (+/-)-13a-f was synthesized by adopting appropriate synthetic routes and was pharmacologically evaluated in the preliminary anticonvulsant screens. The selected bioactive new chemical entities were subjected to ED50 determination and neurotoxicity evaluation. The most active congeners are 7h in MES screen and (+/-)-13b in scPTZ screen which displayed ED50 values of 87 and 110 mg/kg, respectively, as compared to that of STP (ED50 = 277.7 and 115 mg/kg in MES and scPTZ, respectively). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.004

文献信息

• NBS-mediated cyclization of trans-cinnamic alcohols
  作者：Meng-Yang Chang、Chung-Yu Tsai、Ming-Hao Wu

  DOI：10.1016/j.tet.2013.05.110

  日期：2013.8

  An efficient and straightforward three-step synthetic route toward 2,4-disubstituted-3-bromooxetanes 5 with the trans–trans contiguous stereogenic centers is developed from functionalized chalcones 3 via NaBH4-mediated reduction of chalcones 3, followed by NBS-mediated electrophilic cyclization of the resulting trans-cinnamic alcohols 4 in good yield. Skeleton 3 is prepared by Claisen–Schmidt condensation

  通过NaBH 4介导的查耳酮3还原反应，再由NBS介导的亲电反应，从功能化的查耳酮3中开发出一种有效，直接的三步合成路线，以2,4-二取代-3-溴氧杂环丁烷5为反式-反式连续立体中心。以高收率将所得反式肉桂醇4环化。骨架3是通过Claisen-Schmidt缩合取代的芳基醛1和芳基甲基酮或叔丁基甲基酮2制备的。合成路线获得了高收率，并且整个反应过程仅花费了一天。研究了骨架3的取代作用，各种反应条件和合理的机理。
• Spectroscopic identification, structural features, Hirshfeld surface analysis and molecular docking studies on stiripentol: An orphan antiepileptic drug
  作者：Maha S. Almutairi、D.R. Leenaraj、Hazem A. Ghabbour、I. Hubert Joe、Mohamed I. Attia

  DOI：10.1016/j.molstruc.2018.11.088

  日期：2019.3

  Furthermore, the frontier molecular orbital (FMO) analysis, distribution of electric charges on the STP molecule and natural bond orbital (NBO) analysis were investigated using DFT computations. Also, Hirshfeld surface maps of STP and its 2D fingerprint plots were studied to gain insight into different patterns of its intermolecular interactions. Moreover, molecular docking simulations were conducted

  摘要 癫痫影响全球约 5000 万人，但其中只有 70% 被临床使用的抗癫痫药物充分控制。司替戊醇 (STP) 的化学结构与任何其他市售抗癫痫药物显着不同，它被批准作为控制儿童癫痫的附加药物。在当前的研究中已经探索了由密度泛函理论 (DFT) 计算辅助的司替戊醇的详细振动光谱特征。此外，使用 DFT 计算研究了前沿分子轨道 (FMO) 分析、STP 分子上的电荷分布和自然键轨道 (NBO) 分析。此外，还研究了 STP 的 Hirshfeld 表面图及其 2D 指纹图，以深入了解其分子间相互作用的不同模式。
• Fungicidal azole derivatives
  申请人：Uniroyal Chemical Company, Inc.

  公开号：US05691363A1

  公开（公告）日：1997-11-25

  Compounds having the formula ##STR1## wherein Q is ##STR2## R.sup.1 is C.sub.1 -C.sub.8 alkyl; R.sup.2 is C.sub.4 -C.sub.17 heterocyclic aryl, unsubstituted or substituted with one or more C.sub.1 -C.sub.6 alkyl, halo or nitro, containing a sulfur atom, a nitrogen atom, or one or two oxygen atoms; X is nitrogen; and n is 2, 3 or 4, or a stereoisomer thereof. These compounds are useful as fungicides.

  具有以下结构式的化合物 ##STR1## 其中 Q 是 ##STR2## R.sup.1 是 C.sub.1 -C.sub.8 烷基；R.sup.2 是 C.sub.4 -C.sub.17 杂环芳基，未取代或取代一个或多个 C.sub.1 -C.sub.6 烷基、卤素或硝基，含有硫原子、氮原子或一个或两个氧原子；X 是氮；n 是 2、3 或 4，或其立体异构体。这些化合物可用作杀菌剂。
• PROCESS FOR THE PREPARATION OF STIRIPENTOL PARTICLES HAVING A DEFINED PARTICLE SIZE DISTRIBUTION
  申请人：HUBLOT Bernard

  公开号：US20090187034A1

  公开（公告）日：2009-07-23

  The invention relates to a process for the preparation of stiripentol particles having a defined particle size distribution.

  这项发明涉及一种制备具有定义的粒度分布的斯的利本托尔颗粒的方法。
• 一种司替戊醇的制备方法
  申请人：湖南大学

  公开号：CN102690252A

  公开（公告）日：2012-09-26

  本发明涉及一种由化学结构式Ⅰ所示的4-(2-甲基烯丙基)-1,2-苯二酚制备化学结构式Ⅱ所示的司替戊醇的制备方法：4-(2-甲基烯丙基)-1,2-苯二酚经醚化、异构化、氧化反应、缩合反应和还原反应制得司替戊醇；司替戊醇为治疗癫痫病的新药。