1-(3,4-二亚甲氧基)苯基-2-丁酮 | 23023-13-4

• 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
• 中文名称: 1-(3,4-二亚甲氧基)苯基-2-丁酮
• 中文别名: 1-(3,4-亚甲二氧基)苯基-2-丁酮
• 英文名称: 1-(1,3-benzodioxol-5-yl)butan-2-one
• 英文别名: 3,4-methylendioxyphenylbutan-2-one；2-Butanone, 1-(1,3-benzodioxol-5-yl)-
• CAS: 23023-13-4
• 化学式: C₁₁H₁₂O₃
• mdl: MFCD02093417
• 分子量: 192.214
• InChiKey: SWKXHWCUDGJLNA-UHFFFAOYSA-N

物化性质

• 沸点：
  98°C 0,1mm
• 闪点：
  98°C/0.1mm

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• TSCA：
  Yes
• 安全说明：
  S24/25
• 海关编码：
  2932999099

制备方法与用途

合成制备方法

---

用途

---

反应信息

• 作为反应物：
  描述：

  1-(3,4-二亚甲氧基)苯基-2-丁酮 在 乙酸铵 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 1-(1,3-苯并二氧戊环-5-基)丁烷-2-胺
  参考文献：
  名称：

  Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class

  摘要：

  The alpha-ethyl phenethylamine derivative 1-(1,3-benzodioxol-5-yl)-2-butanamine was prepared. An asymmetric synthesis was used to prepare the enantiomers of this compound and the related alpha-methyl homologue (MDA). The racemates and enantiomers of both compounds were evaluated in the two-lever drug discrimination assay in rats trained to discriminate saline from 0.08 mg/kg of LSD tartrate. Stimulus generalization occurred with the racemate and the R-(-) enantiomer of the alpha-methyl homologue and the S-(+) enantiomer of the alpha-ethyl primary amine. No generalization occurred with the other enantiomers or with the N-methyl derivatives of either series. Human psychopharmacology studies revealed that the N-methyl derivative of the title compound was nonhallucinogenic and that it had a new, novel psychoactive effect. It is suggested that this compound is the prototype of a new pharmacologic class that may have value in facilitating psychotherapy and that this class be designated as entactogens.

  DOI：

  10.1021/jm00160a035
• 作为产物：
  描述：

  1-(1,3-benzodioxol-5-yl)butan-1-ol 在 potassium hydrogensulfate 、 过甲酸 、 硫酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 12.0h， 生成 1-(3,4-二亚甲氧基)苯基-2-丁酮
  参考文献：
  名称：

  Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class

  摘要：

  The alpha-ethyl phenethylamine derivative 1-(1,3-benzodioxol-5-yl)-2-butanamine was prepared. An asymmetric synthesis was used to prepare the enantiomers of this compound and the related alpha-methyl homologue (MDA). The racemates and enantiomers of both compounds were evaluated in the two-lever drug discrimination assay in rats trained to discriminate saline from 0.08 mg/kg of LSD tartrate. Stimulus generalization occurred with the racemate and the R-(-) enantiomer of the alpha-methyl homologue and the S-(+) enantiomer of the alpha-ethyl primary amine. No generalization occurred with the other enantiomers or with the N-methyl derivatives of either series. Human psychopharmacology studies revealed that the N-methyl derivative of the title compound was nonhallucinogenic and that it had a new, novel psychoactive effect. It is suggested that this compound is the prototype of a new pharmacologic class that may have value in facilitating psychotherapy and that this class be designated as entactogens.

  DOI：

  10.1021/jm00160a035

文献信息

• Controlled Ring-Opening of Siloxydifluorocyclopropanes for Carbocyclization: Synthesis of Difluorocyclopentenones
  作者：Xiaoning Song、Shuangquan Tian、Ziming Zhao、Dongsheng Zhu、Mang Wang

  DOI：10.1021/acs.orglett.6b01567

  日期：2016.7.15

  A highly controlled ring opening of siloxydifluorocyclopropanes, formed by nBuN4Br-catalyzed difluorocyclopropanation of methyl vinyl ketones bearing a β-alkylthio group by using TMSCF2Br as a unique difluorocarbene source, results in metal difluorohomoenolates with assistance of copper or silver followed by an intramolecular addition and elimination reaction leading to α-gem-difluorocyclopentenones

  硅烷氧基二氟环丙烷的高度受控的开环，是通过将TMSCF 2 Br作为独特的二氟卡宾源，由n BuN 4 Br催化的带有β-烷硫基的甲基乙烯基酮的二氟环丙烷化而形成的，导致金属二氟均戊酸酯在铜或银的辅助下分子内的加成和消除反应有效地导致了α-宝石-二氟环戊烯酮。
• IMMUNOASSAY FOR PYRROLIDINOPHENONES
  申请人：Randox Laboratories Limited

  公开号：US20130210167A1

  公开（公告）日：2013-08-15

  The invention describes antibodies that bind molecules of the pyrrolidinophenone class of synthetic drugs. The antibodies are derived from novel chemical intermediates, haptens and immunogens and are used in methods and kits to detect and quantify pyrrolidinophenones.

  该发明描述了能够结合合成药物吡咯烷基苯酮类分子的抗体。这些抗体来源于新型化学中间体、半抗原和免疫原，并用于检测和定量吡咯烷基苯酮的方法和试剂盒中。
• Extruded fragrance-containing polyvinyl alcohol and use thereof
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：EP0728804A1

  公开（公告）日：1996-08-28

  Described is a composition of matter particularly useful in fabricating toilet rim blocks consisting of: (a) extruded polyvinyl alcohol or partially hydrolyzed polyvinyl acetate with the maximum mole ratio of acetyl moiety:hydroxyl moiety being about 3:1 having a number average molecular weight of from about 15,000 up to about 68,000 containing from 0 up to about 13% by weight of an added polar plasticizer; (b) from about 1 up to about 20% by weight of a compatible fragrance contained within the polyvinyl alcohol or partially hydrolyzed polyvinyl acetate; (c) from 0 up to about 20% by weight of a "foaming agent" which is a first surfactant and which can be a detergent, contained within the polyvinyl alcohol or partially hydrolyzed polyvinyl acetate; (d) from 0 up to about 20% by weight of a hydrophobic silica contained within the polyvinyl alcohol or partially hydrolyzed polyvinyl acetate; (e) from 0 up to about 20% by weight of at least one second surfactant in addition to the "foaming agent"; (f) from 0 up to about 5% by weight of a water-soluble dye; and (g) from 0 up to about 4% by weight of a "foam booster". Also described are processes for preparing such compositions of matter and such toilet rim blocks. When used for the fabrication of toilet rim blocks, the maximum mole ratio of acetyl moiety:hydroxyl moiety is about 1:3.

  所描述的是一种特别适用于制造马桶圈块的物质组合物，由以下成分组成： (a) 挤出的聚乙烯醇或部分水解的聚醋酸乙烯酯，乙酰基与羟基的最大摩尔比约为 3:1，其平均分子量约为 15,000 至 68,000 之间，含有 0 至 13%（按重量计）的添加极性增塑剂； (b) 聚乙烯醇或部分水解的聚醋酸乙烯酯中含有约 1%至约 20%（按重量计）的相容香料； (c) 0 至约 20%（按重量计）的 "发泡剂"，它是第一种表面活性剂，也可以是 洗涤剂，包含在聚乙烯醇或部分水解的聚醋酸乙烯酯中； (d) 聚乙烯醇或部分水解的聚醋酸乙烯酯中所含的疏水性二氧化硅的重量比为 0 至约 20%； (e) 除 "发泡剂 "外，0 至约 20%（按重量计）的至少第二种表面活性剂； (f) 0 至约 5%（按重量计）的水溶性染料；以及 (g) 0 至约 4%（按重量计）的 "泡沫促进剂"。 还描述了制备这种物质组合物和这种马桶圈块的工艺。当用于制造厕圈时，乙酰基分子与羟基分子的最大摩尔比约为 1:3。
• Palladium-catalyzed synthesis of substituted nitroolefins
  作者：Meng-Yang Chang、Chung-Han Lin、Hang-Yi Tai

  DOI：10.1016/j.tetlet.2013.04.038

  日期：2013.6

  A one-pot protocol toward several substituted nitroolefins 4 and 6 starting with substituted acetones 2 and 5 was described. A facile process was carried out for the triflation of substituted acetones 2 and 5 with triflic anhydride (Tf2O) under the basic condition (Cs2CO3) and then palladium-catalyzed cross-coupling of enol triflates 3 with NaNO2 and BINAP in the presence of phase-transfer reagents (n-Bu4NBr) under the refluxing 1,2-dimethoxyethane (DME) in acceptable yields. (C) 2013 Elsevier Ltd. All rights reserved,
• Comparative potencies of 3,4-methylenedioxymethamphetamine (MDMA) analogues as inhibitors of [³ H]noradrenaline and [³ H]5-HT transport in mammalian cell lines
  作者：T Montgomery、C Buon、S Eibauer、P J Guiry、A K Keenan、G J McBean

  DOI：10.1038/sj.bjp.0707473

  日期：2007.12

  Background and purpose:Illegal ‘ecstasy’ tablets frequently contain 3,4‐methylenedioxymethamphetamine (MDMA)‐like compounds of unknown pharmacological activity. Since monoamine transporters are one of the primary targets of MDMA action in the brain, a number of MDMA analogues have been tested for their ability to inhibit [3H]noradrenaline uptake into rat PC12 cells expressing the noradrenaline transporter (NET) and [3H]5‐HT uptake into HEK293 cells stably transfected with the 5‐HT transporter (SERT).Experimental approach:Concentration–response curves for the following compounds at both NET and SERT were determined under saturating substrate conditions: 4‐hydroxy‐3‐methoxyamphetamine (HMA), 4‐hydroxy‐3‐methoxymethamphetamine (HMMA), 3,4‐methylenedioxy‐N‐hydroxyamphetamine (MDOH), 2,5‐dimethoxy‐4‐bromophenylethylamine (2CB), 3,4‐dimethoxymethamphetamine (DMMA), 3,4‐methylenedioxyphenyl‐2‐butanamine (BDB), 3,4‐methylenedioxyphenyl‐N‐methyl‐2‐butanamine (MBDB) and 2,3‐methylenedioxymethamphetamine (2,3‐MDMA).Key results:2,3‐MDMA was significantly less potent than MDMA at SERT, but equipotent with MDMA at NET. 2CB and BDB were both significantly less potent than MDMA at NET, but equipotent with MDMA at SERT. MBDB, DMMA, MDOH and the MDMA metabolites HMA and HMMA, were all significantly less potent than MDMA at both NET and SERT.Conclusions and implications:This study provides an important insight into the structural requirements of MDMA analogue affinity at both NET and SERT. It is anticipated that these results will facilitate understanding of the likely pharmacological actions of structural analogues of MDMA.British Journal of Pharmacology (2007) 152, 1121–1130; doi:10.1038/sj.bjp.0707473; published online 24 September 2007