2-氯-1-(4-甲基苯基)-(9ci)-1-丙酮 | 69673-92-3

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-氯-1-(4-甲基苯基)-(9ci)-1-丙酮
• 中文别名: 2-氯-1-(4-甲基苯基)-1-丙酮；2-氯-1- (4-甲基苯基)-1-丙酮
• 英文名称: 2-chloro-1-(p-tolyl)propan-1-one
• 英文别名: α-chloro-4-methyl propiophenone；2-Chloro-1-(4-methylphenyl)-1-Propanone；2-chloro-1-(4-methylphenyl)propan-1-one
• CAS: 69673-92-3
• 化学式: C₁₀H₁₁ClO
• mdl: MFCD03988532
• 分子量: 182.65
• InChiKey: AVMPEHALQVCQQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  92 °C(Press: 2 Torr)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914700090
• 储存条件：
  室温且干燥环境中保存。

制备方法与用途

2-氯-1-(4-甲基苯基)-1-丙酮可用作有机合成中间体及医药中间体，主要应用于实验室研发和化工生产过程。

反应信息

• 作为反应物：
  描述：

  2-氯-1-(4-甲基苯基)-(9ci)-1-丙酮 在 盐酸 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 (rac)-2-amino-1-(p-tolyl)propan-1-one hydrochloride
  参考文献：
  名称：

  Phase I metabolites of mephedrone display biological activity as substrates at monoamine transporters

  摘要：

  Background and Purpose4‐Methyl‐N‐methylcathinone (mephedrone) is a synthetic stimulant that acts as a substrate‐type releaser at transporters for dopamine (DAT), noradrenaline (NET) and 5‐HT (SERT). Upon systemic administration, mephedrone is metabolized to several phase I compounds: the N‐demethylated metabolite, 4‐methylcathinone (nor‐mephedrone); the ring‐hydroxylated metabolite, 4‐hydroxytolylmephedrone (4‐OH‐mephedrone); and the reduced keto‐metabolite, dihydromephedrone.Experimental ApproachWe used in vitro assays to compare the effects of mephedrone and synthetically prepared metabolites on transporter‐mediated uptake and release in HEK293 cells expressing human monoamine transporters and in rat brain synaptosomes. In vivo microdialysis was employed to examine the effects of i.v. metabolite injection (1 and 3 mg·kg−1) on extracellular dopamine and 5‐HT levels in rat nucleus accumbens.Key ResultsIn cells expressing transporters, mephedrone and its metabolites inhibited uptake, although dihydromephedrone was weak overall. In cells and synaptosomes, nor‐mephedrone and 4‐OH‐mephedrone served as transportable substrates, inducing release via monoamine transporters. When administered to rats, mephedrone and nor‐mephedrone produced elevations in extracellular dopamine and 5‐HT, whereas 4‐OH‐mephedrone did not. Mephedrone and nor‐mephedrone, but not 4‐OH‐mephedrone, induced locomotor activity.Conclusions and ImplicationsOur results demonstrate that phase I metabolites of mephedrone are transporter substrates (i.e. releasers) at DAT, NET and SERT, but dihydromephedrone is weak in this regard. When administered in vivo, nor‐mephedrone increases extracellular dopamine and 5‐HT in the brain whereas 4‐OH‐mephedrone does not, suggesting the latter metabolite does not penetrate the blood–brain barrier. Future studies should examine the pharmacokinetics of nor‐mephedrone to determine its possible contribution to the in vivo effects produced by mephedrone.

  DOI：

  10.1111/bph.13547
• 作为产物：
  描述：

  3-(dimethylamino)-2-methyl-1-(p-tolyl)prop-2-en-1-one 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以69%的产率得到2-氯-1-(4-甲基苯基)-(9ci)-1-丙酮
  参考文献：
  名称：

  Access to α,α-dihaloacetophenones through anodic C C bond cleavage in enaminones

  摘要：

  DOI：

  10.1016/j.tetlet.2021.153575

文献信息

• Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives
  作者：Aoife M. Kearney、Linda Murphy、Chloe C. Murphy、Kevin S. Eccles、Simon E. Lawrence、Stuart G. Collins、Anita R. Maguire

  DOI：10.1016/j.tet.2021.132091

  日期：2021.5

  The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent

  描述了通过NCS介导的氯化级联反应从相应的α-亚磺酰基酮合成一系列新型α-亚磺酰基-β-氯烯酮的方法。已经研究了反应范围，并且已经合成了带有烷基和芳硫基取代基的化合物。在大多数情况下，Ž α-硫基-β-chloroenones形成作为主要产品，而在β碳位上的取代基的变化导致了立体选择性的改变。的Stille交叉偶联与Ž导致的选择性形成α-硫基-β-chloroenones Ž硫基查耳酮，而Ë α-硫基-β-chloroenones没有在相同条件下发生反应。Z的氧化α-硫基-β-chloroenones随后异构化，导致Ë α -亚磺酰基- β-chloroenones。的Stille交叉偶联与Ë α -亚磺酰基- β-chloroenones产生的ë亚磺酰基查耳酮。无论是ë或Ž亚磺酰基的查耳酮可以通过改变氧化和的Stille交叉偶联的序列来获得。
• One-Pot Synthesis of α-Chloro Ketones from Secondary Alcohols Using<i>N</i>,<i>N</i>-Dichloro-<i>p</i>-toluenesulfonamide
  作者：Yong Hae Kim、In Sang Lee、Sang Chul Lim

  DOI：10.1246/cl.1990.1125

  日期：1990.7

  Various alkyl aryl secondary alcohols reacted with N,N-dichloro-p-toluenesulfonamide (N,N-dichloramine-T) in CH3CN at 35 °C to give the corresponding α-chloro ketones in excellent yields under mild and neutral conditions.

  多种烷基芳基仲醇在35°C下与N,N-二氯对甲苯磺酰胺（N,N-二氯胺-T）在CH3CN中反应，在温和中性条件下以优异的产率得到了相应的α-氯代酮。
• Domino Radical Addition/Oxidation Sequence with Photocatalysis: One-Pot Synthesis of Polysubstituted Furans from α-Chloro-Alkyl Ketones and Styrenes
  作者：Shuang Wang、Wen-Liang Jia、Lin Wang、Qiang Liu、Li-Zhu Wu

  DOI：10.1002/chem.201602053

  日期：2016.9.19

  A new domino reaction has been developed that allows the combination of styrenes and α‐alkyl ketone radicals to afford a wide array of polysubstituted furans in good to excellent yields under mild and simple reaction conditions. The key to success of this novel protocol is the use of photocatalyst fac‐Ir(ppy)3 and oxidant K2S2O8. Mechanistic studies by a radical scavenger and photoluminescence quenching

  已开发出一种新的多米诺反应，该反应允许苯乙烯和α-烷基酮自由基的组合在温和简单的反应条件下以良好或优异的收率提供各种各样的多取代呋喃。该新协议成功的关键是使用光催化剂fac ‐Ir（ppy）3和氧化剂K 2 S 2 O 8。通过自由基清除剂和光致发光猝灭的机理研究表明，自由基加成/氧化途径是可行的。
• Efficient α‐Chlorination of Aryl Ketones Using Aluminum Chloride/Urea–Hydrogen Peroxide in Ionic Liquid
  作者：Jong Chan Lee、Hyun Jung Park

  DOI：10.1080/00397910500449641

  日期：2006.4.1

  Abstract Effective α‐chlorination reactions of aryl ketones into the corresponding α‐chloroketones have been accomplished with aluminum chloride hexahydrate and urea–hydrogen peroxide in [bmim]BF4 ionic liquid.

  摘要 在 [bmim]BF4 离子液体中，使用六水氯化铝和过氧化氢可实现芳基酮有效的 α-氯化反应生成相应的 α-氯酮。
• Iodine(III)-Mediated Oxidative Hydrolysis of Haloalkenes: Access to α-Halo Ketones by a Release-and-Catch Mechanism
  作者：Antoine Jobin-Des Lauriers、Claude Y. Legault

  DOI：10.1021/acs.orglett.5b03345

  日期：2016.1.4

  An unprecedented iodine(III)-mediated oxidative transposition of vinyl halides has been accomplished. The products obtained, α-halo ketones, are useful and polyvalent synthetic precursors. There are only a handful of reported examples of the direct conversion of vinyl halides to their corresponding α-halo carbonyl compounds. Insights into the mechanism and demonstration that this synthetic transformation

  已经实现了空前的碘（III）介导的乙烯基卤化物的氧化转座。获得的产物α-卤代酮是有用的多价合成前体。仅有少数报道的卤代乙烯直接转化为其相应的α-卤代羰基化合物的实例。报告了对该机理的见解，并证明了该合成转化可以在对映选择性条件下进行。