1,3-bis(3,4-methylenedioxyphenyl)-2-propanone

• 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: 1,3-bis(3,4-methylenedioxyphenyl)-2-propanone
• 英文别名: Piperonyl ketone；1,3-bis(1,3-benzodioxol-5-yl)propan-2-one
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: WFYBOCPLYWJYBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  1,3-bis(3,4-methylenedioxyphenyl)-2-propanone 在 吡啶 、 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 13.0h， 生成 2-N-acetylamino-1,3-bis(3,4-methylenedioxyphenyl)-propane
  参考文献：
  名称：

  Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents

  摘要：

  Structural derivatives of 4-MTA, an illegal amphetamine analogue have been previously shown to have anticancer effects in vitro. In this study we report the synthesis of a series of novel 1,3-bis(aryl)-2-nitro-1-propene derivatives related in structure to 4-MTA. A number of these compounds containing a classic nitrostyrene structure are shown to have antiproliferative activities in vitro in a range of malignant cell lines, particularly against Burkitt's lymphoma derived cell lines, whilst having no effect on 'normal' peripheral blood mononuclear cells. Such effects appear to be independent of the serotonin transporter, a high affinity target for amphetamines and independent of protein tyrosine phosphatases and tubulin dynamics both of which have been previously associated with nitrostyrene-induced cell death. We demonstrate that a number of these compounds induce caspase activation, PARP cleavage, chromatin condensation and membrane blebbing in a Burkitt's lymphoma derived cell line, consistent with these compounds inducing apoptosis in vitro. Although no specific target has yet been identified for the action of these compounds, the cell death elicited is potent, selective and worthy of further investigation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.054
• 作为产物：
  描述：

  5-(2-nitroethyl)benzo[1,3]dioxole 在 chromium dichloride 、 potassium fluoride 、 sodium tetrahydroborate 、 盐酸二甲胺 、 silica gel 作用下， 以 四氢呋喃 、 氯仿 、 异丙醇 、 甲苯 为溶剂， 反应 0.42h， 生成 1,3-bis(3,4-methylenedioxyphenyl)-2-propanone
  参考文献：
  名称：

  Synthesis, Chemical Transformation and Antimicrobial Activity of a Novel Class of Nitroolefins: 1,3-Diaryl-2-nitroprop-1-enes

  摘要：

  synthesis of novel, biologically active 1,3-diaryl-2-nitroprop-1-enes (4) is reported. The synthesis involves condensation between aromatic aldehydes (1) and beta-aryl nitroethanes (3). The chemical transformation of the nitro group in diaryl nitropropenes to a carbonyl function has resulted in a new route to the synthesis of an alpha-hydroxy analog (7c) of a naturally occurring 3, 3'. 4, 4'-tetramethoxy chalcone. The antimicrobial activity of the 1, 3-diaryl-2-nitroprop-1-enes (4a-j) was tested against three gram positive bacteria, two gram negative bacteria and two fungi. These compounds exhibited broad spectrum and microbial activity.

  DOI：

  10.1080/00397919408011304

文献信息

• Palladium-Catalyzed Enantioselective C–H Aminocarbonylation: Synthesis of Chiral Isoquinolinones
  作者：Hui Han、Tao Zhang、Shang-Dong Yang、Yu Lan、Ji-Bao Xia

  DOI：10.1021/acs.orglett.9b00315

  日期：2019.3.15

  A Pd-catalyzed enantioselective C–H carbonylation by desymmetrization was developed with commercially available L-pyroglutamic acid as chiral ligand. Isoquinolinones were successfully obtained with good yields and high enantioselectivities. Mechanistic studies and DFT calculations provided a reasonable reaction pathway.

  利用可商购的L-焦谷氨酸作为手性配体，开发了一种Pd催化的非对称化CH羰基化对映体。异喹啉酮以高收率和高对映选择性成功获得。机理研究和DFT计算提供了合理的反应途径。
• Synthesis of α-benzylated amides via electrocatalytic Favorskii rearrangement of 1, 3-diarylacetones
  作者：Wei Liu、Wei Huang、Tianlei Lan、Haijuan Qin、Cheng Yang

  DOI：10.1016/j.tet.2018.03.033

  日期：2018.5

  Electrolysis of 1,3-diarylacetones with aliphatic amines in Bu4NI/CH3CN to racemic Favorskii amides via benzyl group rearrangement has been developed. The electroconversion is easily conducted in a simple undivided cell under constant-current conditions at room temperature. The electrocatalytic Favorskii rearrangement of 1,3-diarylacetones including electron-withdrawing substituents was favored and

  已开发了通过苄基重排将1，3-二芳基丙酮与Bu 4 NI / CH 3 CN中的脂肪族胺电解成外消旋的Favorskii酰胺。在室温下恒定电流条件下，在简单的不分格电池中可以轻松进行电转换。包括吸电子取代基的1，3-二芳基丙酮的电催化Favorskii重排是有利的，并且α-苄基酰胺具有良好的产率。当使用几种不对称酮作为底物时，观察到具有中等区域选择性的这种重排。该化学方法还提供了在酰胺的α-位上构建手性中心的有效方法。
• [EN] PROCESS FOR PREPARING SUBSTITUTED AZETIDINONES<br/>[FR] PROCEDE DE PREPARATION D'AZETIDINONES A SUBSTITUTION
  申请人：MERCK & CO., INC.

  公开号：WO1997016448A1

  公开（公告）日：1997-05-09

  (EN) The present invention relates to the process for the preparation of the substituted azetidinone having formula (I) comprising a convergent synthesis.(FR) Cette invention porte sur un procédé de préparation d'azétidinone à substitution répondant à la formule (I) comprenant une synthèse convergente.

  (中文) 本发明涉及一种制备具有式(I)的取代氮杂四元环的方法，包括收敛合成。
• Processes for producing optically active 2-amino-1-phenylethanol derivatives
  申请人：Daicel Chemical Industries, Ltd.

  公开号：US20030143701A1

  公开（公告）日：2003-07-31

  An (R)-2-amino-1-phenylethanol derivative shown by the general formula (IIa) 1 wherein R 1 and R 5 represent a hydrogen atom, etc.; R 2 , R 3 and R 4 independently represent a halogen atom, etc., or a salt thereof, can readily be produced (1) by permitting a microorganism belonging to the genus Rhodosporidium, the genus Comamonas or the like to act on a mixture of corresponding (R)-form and (S)-form to asymmetrically utilize, or (2) by permitting a microorganism belonging to the genus Lodderomyces, the genus Pilimelia or the like to act on a corresponding aminoketone derivative to asymmetrically reduce. An (R,R)-1-phenyl-2-[(2-phenyl-1-alkylethyl)amino]ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (IIa) or a salt thereof. Said derivative is useful as an intermediate for producing an anti-obesity agent and so on.

  通式（IIa）所示的（R）-2-氨基-1-苯乙醇衍生物，其中R1和R5代表氢原子等；R2、R3和R4分别独立地表示卤素原子等，或其盐，可以通过（1）让属于红孢霉属、普通小杆菌属或类似菌属的微生物作用于相应（R）-型和（S）-型的混合物以不对称利用，或（2）让属于洛德罗霉属、皮利米利亚属或类似菌属的微生物作用于相应的氨基酮衍生物以不对称还原而轻松制备。可以从式（IIa）化合物或其盐中轻松获得具有高光学纯度的（R，R）-1-苯基-2-［（2-苯基-1-烷基乙基）氨基］乙醇衍生物。所述衍生物可用作生产抗肥胖剂等中间体。
• Enantioselective Michael Addition/Cyclization/Desymmetrization Sequence of Prochiral Cyclic Hemiacetals and Nitroolefins: Synthesis of Chiral Oxygen-Bridged Bicyclic Compounds
  作者：Yu-Jie Li、Xue-Jiao Lv、Yan-Kai Liu

  DOI：10.1021/acs.orglett.2c03815

  日期：2022.12.23

  The organocatalytic enantioselective Michael addition of functionalized prochiral cyclic hemiacetals and nitroolefins has been developed under cooperative enamine and hydrogen bond catalysis. The obtained chiral hemiacetal intermediates could be used in the subsequent diastereocontrolled cyclization/desymmetrization divergent process to access (1) 9-oxabicyclo[3.3.1]nonane or 8-oxabicyclo[3.2.1]octane

  在协同烯胺和氢键催化下，开发了功能化前手性环状半缩醛和硝基烯烃的有机催化对映选择性迈克尔加成反应。获得的手性半缩醛中间体可用于随后的非对映控制环化/去对称发散过程，以通过氧碳正离子介导的 Friedel-Crafts 获得 (1) 9-氧杂双环[3.3.1]壬烷或 8-氧杂双环[3.2.1] 辛烷骨架环化，和 (2) 2,9-二氧杂双环[3.3.1]壬烷框架通过分子内亲核环化。实验结果表明，存在相邻组的参与控制去对称化过程的非对映选择性。