苯基丙酮 | 103-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯基丙酮
• 中文别名: 苄基丙酮,苯基-2-丙酮,苄基甲基酮；甲基苄基甲酮；1—苯基—2—丙酮；苄基甲基酮；1-苯基-2-丙酮；甲基苄基酮；丙酮苯；苄基甲基甲酮
• 英文名称: 1-phenyl-acetone
• 英文别名: Phenylacetone；1-phenylpropan-2-one；benzyl methyl ketone
• CAS: 103-79-7
• 化学式: C₉H₁₀O
• 分子量: 134.178
• InChiKey: QCCDLTOVEPVEJK-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  <b> <p></p> </b>

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

在三种动物的强化9000克肝脏匀浆上清液中，观察到了明显的差异，这些匀浆上清液能够将1-苯基-2-丙酮还原为相应的醇。在大鼠的匀浆中，这种代谢的酮还原作用可以忽略不计，而在兔子的匀浆中则非常显著；豚鼠肝脏匀浆具有中等程度的还原能力。1-苯基-2-丙醇的代谢氧化在所有三种动物中均可忽略不计。在大鼠和豚鼠中，amphetamine（安非他命）和N-n-丙基amphetamine的脱氨量在体外大约相等，但在兔子肝脏匀浆中，这一脱氨量是前两者的两到三倍。在体外代谢中，从N-n-丙基amphetamine形成的脱氨产物大约是从amphetamine代谢中形成的产物的三倍。

Marked differences were observed, in the ability of fortified 9000 g liver homogenate supernatants from three species to reduce 1-phenyl-2-propanone to the corresponding alcohol. This metabolic keto-reduction was negligible in homogenates from the rat and extensive in the rabbit; guinea-pig liver homogenates had intermediate ability. Metabolic oxidation of 1-phenyl-2-propanol was negligible in all three species. The amount of deamination of amphetamine and of N-n-propylamphetamine was approximately equal, in vitro, in rats and guinea-pigs but two to three times greater in liver homogenates from rabbits. Approximately three times more deaminated products were formed from the in vitro metabolism of N-n-propylamphetamine than from amphetamine metabolism by all three species.

来源:Hazardous Substances Data Bank (HSDB)

代谢

2-硝基-1-苯基丙烷与兔肝微粒体一起孵化时，发现苯乙酮是形成的主要代谢物。该反应的酶性质通过产物随微粒体蛋白增加以及依赖于NADPH和氧气得以证明。此外，苯巴比妥诱导显著增加了苯乙酮的形成。一氧化碳降低了反应，表明涉及到了金属酶。使用H2(18)O的实验表明，羰基氧来自于水。这表明2-硝基-1-苯基丙烷的微粒体代谢涉及一个酶促步骤，随后是中间体的化学水解，可能是一种二级硝基酸。

Phenylacetone was found to be the major metabolite formed when 2-nitro-1-phenylpropane was incubated with rabbit liver microsomes. The enzymatic character of the reaction was demonstrated by the increase of product with microsomal protein and dependency on NADPH and oxygen. Furthermore, phenobarbital induction markedly increased the formation of phenylacetone. Carbon monoxide decreased the reaction indicating the involvement of a metalloenzyme. Experiments with H2(18)O indicated that the carbonyl oxygen originated from water. It is suggested that the microsomal metabolism of 2-nitro-1-phenylpropane involves an enzymatic step followed by chemical hydrolysis of an intermediate, possibly a secondary nitronic acid.

来源:Hazardous Substances Data Bank (HSDB)

代谢

苯丙胺通过高度纯化的鼠肝线粒体进行氧化脱氨。这种单胺氧化酶（MAO）是线粒体外膜的一种酶，其活性大约是微粒体MAO的两倍。在无氧条件下，线粒体可以将苯丙酮还原为苯异丙醇，苯丙酮是苯丙胺的一个重要代谢物。这种酮还原酶定位于线粒体内膜或其基质中。

Amphetamine is deaminated oxidatively by highly purified rat liver mitochondria. This monoamineoxidase (MAO) is an enzyme of the mitochondrial outer membrane and its activity is about two times higher than that of the microsomal MAO. Anaerobic incubations with mitochondria reduce phenylacetone, an important metabolite of amphetamine, to phenylisopropanol. The ketoreductase is localized in the mitochondrial inner membrane or its matrix.

来源:Hazardous Substances Data Bank (HSDB)

代谢

芬乙茶碱在人体内通过两条途径代谢。除了之前描述的降解成安非他命和7-氧乙基茶碱外，芬乙茶碱还会进一步发生氧化N-脱烷基化，生成7-氨基乙基茶碱和苯乙酮。

Fenetylline is metabolized in humans on two pathways. In addition to previously described degradation to amphetamine and 7-oxyethyltheophylline fenetylline undergoes moreover oxydative N-dealkylation to yield 7-aminoethyltheophylline and phenylacetone.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

鉴定和使用：苯基-2-丙酮是安非他明和甲基安非他明（冰毒）的直接前体，是DEA（美国缉毒局）规定的二级管制物质。人体研究：由于新前体苯基-2-丙酮的引入，非法甲基安非他明的质量和数量最近有所增加。动物研究：合成了各种环甲氧基化-1-苯基-2-丙醇和1-苯基-2-丙酮，并对其进行了药理评估。大多数化合物具有类似抑制剂的活性。这些酮类化合物很容易被兔肝微粒体还原。

IDENTIFICATION AND USE: Phenyl 2-propanone is immediate precursor to amphetamine and methamphetamine, and a DEA Schedule II substance. HUMAN STUDIES: The quality and quantity of illicit methamphetamine has recently increased due to introduction of a new precursor, phenyl 2-propanone. ANIMAL STUDIES: Various ring-methoxylated 1-phenyl-2-propanols and 1-phenyl-2-propanones were synthesized and pharmacologically evaluated. Most compounds had depressant-like activity. The ketones were readily reduced by rabbit liver microsomes.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中毒物清除。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用温水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒物A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于昏迷、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注5%葡萄糖水（D5W），以“保持开放”的最小流量……。如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸钠林格氏液（LR）。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。使用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。/毒素A和B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

最近，由于引入了新的前体1-苯基-2-丙酮（P2P），非法甲基苯丙胺的质量和数量有所增加。...

/OTHER TOXICITY INFORMATION/ The quality and quantity of illicit methamphetamine has recently increased due to introduction of a new precursor, 1-phenyl-2-propanone (P2P). ...

来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

制备方法

1. 苯基丙酮（1）的制备方法是首先将苯甲醛与2-氯丙酸甲酯反应，然后水解、脱羧得到粗产品。在水溶液中调节pH至6后，用乙酸乙酯萃取，水相再用25% K₂CO₃溶液处理至pH=6，之后继续用乙酸乙酯处理，最后蒸馏粗产品得产品。

2. 烟草：FC，56。

3. 制法：

   • 将294g（0.5mol）六水合硝酸钍溶于约450mL水中。
   • 搅拌下慢慢加入由无水碳酸钠106g（1mol）溶于400mL水配成的溶液。碳酸钍沉淀析出。尽可能倾出水层，用500mL水倾洗。
   • 加入浮石（4～8目）200g混合均匀。在一大蒸发皿中搅拌加热蒸发，制成粉状。
   • 过筛，得约250g白色粉状物，其中主要含有碳酸钍，并含有氧化钍。可以使用更多的浮石制备约1400g的浮石催化剂。

苯基丙酮（1）：将制得的浮石催化剂置于加热管中，在400～450℃氮气饱和下加热6～12h，转化为氧化钍。于400～450℃滴加由苯乙酸（2）170g（1.25mol）与225g冰醋酸配成的溶液，控制滴加速度为25～30滴/次，依次用碱、水洗涤。合并有机层，无水硫酸镁干燥，蒸出乙醚。

剩余物减压分馏，收集102～103℃/2.67kPa的馏分，得苯基丙酮（1）85g，收率51%。剩余物主要是二苄基酮。将其转移至一小蒸馏瓶中蒸馏，收集200℃/2.8kPa的馏分，得二苄基酮，熔点34～35℃。

合成制备方法

与上述制备方法相同。

用途简介

苯基丙酮用作有机中间体，用于合成敌鼠钠盐；医药中间体，用于合成苯丙胺、苯基异丙胺等。

用途

苯基丙酮同样用于上述用途。

反应信息

• 作为反应物：
  描述：

  苯基丙酮 在 rhodium(III) chloride 、 氢气 作用下， 以 2,2,2-三氟乙醇 为溶剂， 100.0 ℃ 、5.0 MPa 条件下， 反应 10.0h， 以91%的产率得到正丙基环己烷
  参考文献：
  名称：

  溶剂决定了使用未连接的 RhCl3 作为催化剂前体的芳香酮加氢产物

  摘要：

  烷基环己烷被以高选择性合成通过使用无配体的RhCl芳族酮的组合加氢/加氢脱氧3如三氟乙醇作为溶剂的预催化剂。真正的催化剂由反应过程中原位生成的铑纳米颗粒 (Rh NPs) 组成。在相对温和的条件下，一系列共轭和非共轭芳族酮被直接加氢脱氧成相应的饱和环己烷衍生物。发现溶剂是改变酮氢化选择性的决定因素。环己基烷基醇是以水为溶剂的产物。

  DOI：

  10.1039/d1cy01504d
• 作为产物：
  描述：

  1-丙烯基苯 在 5Ni⁽²⁺⁾*2C₄₈H₂₆N₄O₈^(4-)*4H₂O*O^(2-) 作用下， 以 乙腈 为溶剂， 反应 28.0h， 生成 苯基丙酮
  参考文献：
  名称：

  Highly thermally stable heterogeneous catalysts: study of 0D and 3D porphyrinic MOFs

  摘要：

  基于卟啉的MOFs作为非均相催化剂展现出对烯烃氧化具有高催化活性、可循环利用性和选择性。

  DOI：

  10.1039/c7ce01702b
• 作为试剂：
  描述：

  氰基丙酮 在 苯基丙酮 作用下， 以33%的产率得到2-acetyl-3-methylpent-2-enedinitrile
  参考文献：
  名称：

  Substituted 2-Aminothiopen-derivatives: A potential new class of GluR6-Antagonists

  摘要：

  In the course of search for new therapeutic agents against epilepsy new inhibitors for the kainate receptor subtypes GluR5 and GluR6 were synthesized.We were able to synthesize new substituted thieno[2,3-d]pyrimidines 3a,b, 4a,b, Sa,b as well as thiophene-3-carboxamides 2a-d and a multitude of substituted 4-methyl-5-phenylthiophene-3-carboxylic acids.All compounds described herein were tested for their antagonistic effect towards the kainate receptor subtypes GluR5 and GluR6. The highest activity was observed for ethyl 2-amino-4-methyl-5-phenylthiophene-3-carboxylate 1c with an IC50 = 0.75 mu M at the GluR6 receptor. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.09.025

文献信息

• Thioether-linked dihydropyrrol-2-one analogues as PqsR antagonists against antibiotic resistant Pseudomonas aeruginosa
  作者：Shekh Sabir、Dittu Suresh、Sujatha Subramoni、Theerthankar Das、Mohan Bhadbhade、David StC. Black、Scott A. Rice、Naresh Kumar

  DOI：10.1016/j.bmc.2020.115967

  日期：2021.2

  Pseudomonas quinolone system (pqs) is one of the key quorum sensing systems in antibiotic-resistant P. aeruginosa and is responsible for the production of virulence factors and biofilm formation. Thus, synthetic small molecules that can target the PqsR (MvfR) receptor can be utilized as quorum sensing inhibitors to treat P. aeruginosa infections. In this study, we report the synthesis of novel thioether-linked

  的假单胞菌喹诺酮系统（PQS）是抗生素抗性的关键群体感应系统的一个铜绿假单胞菌和是负责生产的毒力因子和生物膜形成。因此，可以靶向 PqsR (MvfR) 受体的合成小分子可用作群体感应抑制剂来治疗铜绿假单胞菌感染。在这项研究中，我们报告了新型硫醚连接的二氢吡咯-2-one (DHP) 类似物作为 PqsR 拮抗剂的合成。含有 2-巯基吡啶键的化合物7g在铜绿假单胞菌中有效抑制pqs系统，IC 50为 32 µMPAO1。此外，这些抑制剂在不影响浮游生物生长的情况下显着减少了细菌聚集和生物膜形成。分子对接研究表明，这些抑制剂作为竞争性拮抗剂与 MvfR 的配体结合域结合。
• Methodology Development in Directed Evolution: Exploring Options when Applying Triple-Code Saturation Mutagenesis
  作者：Ge Qu、Richard Lonsdale、Peiyuan Yao、Guangyue Li、Beibei Liu、Manfred T. Reetz、Zhoutong Sun

  DOI：10.1002/cbic.201700562

  日期：2018.2.2

  Directed evolution: Two strategies regarding the application of triple‐code saturation mutagenesis (TCSM) at multiresidue sites of the T. brockii alcohol dehydrogenase (TbSADH) by using distinct reduced amino‐acid alphabets are compared. By using prochiral tetrahydrofuran‐3‐one, highly R‐ and S‐selective variants are obtained with minimal screening. The origin of stereoselectivity is provided by molecular

  定向进化：关于三重码饱和诱变（TCSM）的在所述的多残留部位应用的两种策略布氏热厌氧杆菌醇脱氢酶（TbSADH）通过使用不同的减小的氨基酸字母进行比较。通过使用前手性四氢呋喃-3-酮，只需很少的筛选即可获得高度R和S选择性的变体。立体选择性的起源是由分子动力学模拟提供的。
• Organocerium additions to proline-derived hydrazones: synthesis of enantiomerically enriched amines
  作者：Scott E. Denmark、James P. Edwards、Theodor Weber、David W. Piotrowski

  DOI：10.1016/j.tetasy.2010.04.042

  日期：2010.5

  The addition of organocerium reagents (from both organolithium and organomagnesium precursors) to chiral aldehyde hydrazones prepared from 1-aminoproline derivatives has been studied. The additions proceed in good yield and high diastereoselectivity and with good nucleophile (Me, n-Bu, i-Pr, t-Bu, Ph, etc.) and substrate scope (alkyl, alkenyl and aryl). The resulting hydrazines can be converted to

  已经研究了将有机铈试剂（来自有机锂和有机镁前体）添加到由1-氨基脯氨酸衍生物制备的手性醛中。添加以高收率和高非对映选择性以及良好的亲核试剂（Me，n- Bu，i- Pr，t- Bu，Ph等）和底物范围（烷基，烯基和芳基）进行。生成的肼可通过氢解（阮内镍）的N–N键裂解或通过Li / NH 3的酰化和裂解而转化为胺。。通过改变取代基以包括更多的配位原子（氧和氮）以及去除配位原子，研究了侧链对非对映选择性的影响。带有2-甲氧基乙氧基甲基的SAMEMP助剂具有最高的非对映选择性。值得注意的是，带有简单甲基和异丁基取代基的助剂也具有很高的选择性。给出了选择性起源的假设。
• Transaminase-mediated synthesis of enantiopure drug-like 1-(3′,4′-disubstituted phenyl)propan-2-amines
  作者：Ágnes Lakó、Zsófia Molnár、Ricardo Mendonça、László Poppe

  DOI：10.1039/d0ra08134e

  日期：——

  Transaminases (TAs) offer an environmentally and economically attractive method for the direct synthesis of pharmaceutically relevant disubstituted 1-phenylpropan-2-amine derivatives starting from prochiral ketones. In this work, we report the application of immobilised whole-cell biocatalysts with (R)-transaminase activity for the synthesis of novel disubstituted 1-phenylpropan-2-amines. After optimisation

  转氨酶 (TA) 为从前手性酮开始直接合成药学相关的二取代 1-苯基丙-2-胺衍生物提供了一种环境和经济上有吸引力的方法。在这项工作中，我们报道了具有( R )-转氨酶活性的固定化全细胞生物催化剂在合成新型双取代1-苯基丙-2-胺中的应用。经过不对称合成优化后，( R )-对映体的转化率可达 88-89%，ee 为 >99%，而 ( S )-对映体则可以作为相应外消旋胺在动力学中的未反应部分选择性地获得。分辨率为 >48% 转换率和 >95% ee。
• NAPHTHALENE-BASED INHIBITORS OF ANTI-APOPTOTIC PROTEINS
  申请人：Pellecchia Maurizio

  公开号：US20090105319A1

  公开（公告）日：2009-04-23

  Methods of using apogossypol and its derivatives for treating inflammation is disclosed. Also, there is described a group of compounds having structure A, or a pharmaceutically acceptable salt, hydrate, N-oxide, or solvate thereof are provided: wherein each R is independently selected from the group consisting of H, C(O)X, C(O)NHX, NH(CO)X, SO 2 NHX, and NHSO 2 X, wherein X is selected from the group consisting of an alkyl, a substituted alkyl, an aryl, a substituted aryl, an alkylaryl, and a heterocycle. Compounds of group A may be used for treating various diseases or disorders, such as cancer.

  使用阿波戈司宝及其衍生物治疗炎症的方法被披露。此外，还描述了一组具有结构A的化合物，或其药学上可接受的盐、水合物、N-氧化物或溶剂化合物： 其中每个R独立地选自H、C(O)X、C(O)NHX、NH(CO)X、SO2NHX和NHSO2X组成的组，其中X选自烷基、取代烷基、芳基、取代芳基、烷基芳基和杂环的组。A组化合物可用于治疗各种疾病或疾病，如癌症。

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