2',4'-二氯苯戊酮 | 61023-66-3

• 物质功能分类: 化学农药原药 - 杀菌剂 - 唑类杀菌剂
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2',4'-二氯苯戊酮
• 中文别名: 2',4'-二氯苯基-1-戊酮；2',4'-二氯代苯戊酮；2,4-二氯苯戊酮
• 英文名称: 1-(2,4-dichlorophenyl)pentan-1-one
• 英文别名: 1-(2,4-dichlorophenyl)-n-pentan-1-one；2',4'-Dichlorovalerophenone
• CAS: 61023-66-3
• 化学式: C₁₁H₁₂Cl₂O
• mdl: MFCD09028061
• 分子量: 231.122
• InChiKey: XVWXSWROOLWNCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  297.3±20.0 °C(Predicted)
• 密度：
  1.20
• 稳定性/保质期：
  避免接触氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2914700090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

化学性质
本品为无色固体，不溶于水，但能溶解于苯和甲苯。

用途
2,4-二氯苯基-1-戊酮是杀菌剂己唑醇的中间体，也用作农药己唑醇的合成原料。

生产方法
其制备方法是以间二氯苯为原料，在无水AlCl₃存在下与戊酰氯发生傅氏反应而得到。

反应信息

• 作为反应物：
  描述：

  2',4'-二氯苯戊酮 在 sodium hydroxide 、 双氧水 作用下， 以 乙酸酐 、 丙酮 为溶剂， 反应 0.75h， 生成 (2,4-Dichloro-phenyl)-(2-propyl-oxiranyl)-methanone
  参考文献：
  名称：

  新型偶氮基丙醇酮及相关化合物的合成及口服抗真菌活性。

  摘要：

  为了找到口服活性抗真菌剂，合成了新的咪唑基-和1,2,4-三唑基丙醇酮I和相关化合物II-IV。化合物I衍生自酮V（方法A），α-二酮IX（方法B），α-羟基酮X（方法C），α-氯酮XII（方法D）和烯酮VI（方法E）。使用N，N'-羰基二咪唑，亚硫酰氯，N，N'-（硫代羰基）二咪唑，溴氯甲烷，2,2-二甲氧基丙烷和环己酮将由I与NaBH4合成的二元醇II环化为五元环状化合物III。二甲基缩酮。通过Grignard反应（方法F），X的羟甲基化（方法G）和酮XXI与1-[（（三甲基甲硅烷基）甲基] -1，2，4-三唑（方法H）的反应，由I合成二元醇IV。通过评价肉汤对三种真菌的稀释MIC值和对白色念珠菌假菌丝体的抑制作用，检查了化合物I-IV的体外抗真菌活性，并在小鼠和小鼠体内检查了它们对亚急性系统性念珠菌病的口服药效。豚鼠浅表皮肤癣菌病。化合物2、12、38、39和92表现出较强的口服抗真

  DOI：

  10.1021/jm00389a016
• 作为产物：
  描述：

  N-甲氧基-n-甲基-2,4-二氯苯甲酰胺 、 正丁基锂 在 盐酸 、 乙酸乙酯 、 Brine 、 Sodium sulfate-III 、 crude product 、 Isohexane ethyl acetate 、 silica 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以to yield 1-(2,4-dichloro-phenyl)-pentan-1-one as a brown oil的产率得到2',4'-二氯苯戊酮
  参考文献：
  名称：

  Organic compounds

  摘要：

  这里描述了一些嘧唑并[5.1-b]噁唑衍生物，它们可作为促肾上腺皮质激素释放因子（CRF1）受体拮抗剂。

  公开号：

  US07994203B2

文献信息

• Aerobic Oxidative Dehydrogenation of Ketones to 1,4-Enediones
  作者：Bao-Yin Zhao、Xing-Long Zhang、Rui-Li Guo、Meng-Yue Wang、Ya-Ru Gao、Yong-Qiang Wang

  DOI：10.1021/acs.orglett.0c04174

  日期：2021.2.19

  An efficient and unprecedented strategy for the synthesis of 1,4-enediones from saturated ketones has been developed via palladium-catalyzed oxidative dehydrogenation. The protocol employs molecular oxygen as the sole oxidant and represents an atom- and step-economic process. The approach showed broad substrate scope, good functional group tolerance, and complete E-stereoselectivity. The reaction mechanism

  通过钯催化的氧化脱氢，已经开发出一种有效且空前的从饱和酮合成1,4-二烯酮的策略。该协议采用分子氧作为唯一的氧化剂，代表了原子经济和逐步经济的过程。该方法显示出广泛的底物范围，良好的官能团耐受性和完全的E-立体选择性。通过氘标记实验和中间实验研究了反应机理。
• Efficient use of trimethylsulfonium methylsulfate as a reagent for the epoxidation of carbonyl-containing compounds
  作者：Julie Forrester、Ray V. H. Jones、Peter N. Preston、Elizabeth S. C. Simpson

  DOI：10.1039/a907053b

  日期：——

  A process for the efficient conversion of trimethylsulfonium methylsulfate into dimethylsulfonium methanide, thence epoxides, has been devised. Thus dimethyl sulfate and dimethyl sulfide are caused to react in the presence of either a mineral acid or an organic acid. The anion of trimethylsulfonium methyl sulfate is converted by the acid into methyl hydrogen sulfate, which in turn reacts with excess dimethyl sulfide to form trimethylsulfonium hydrogen sulfate. The outcome is that both methyl groups of dimethyl sulfate are converted into the desired trimethylsulfonium salt, thence dimethylsulfonium methanide; the process is mediated by low boiling dimethyl sulfide which can be recycled, and the by-product (K2SO4) is more easily disposed of than potassium methyl sulfate.

  现已设计出一种将甲基硫酸三甲锍有效转化为甲烷化二甲锍，进而转化为环氧化物的工艺。这样，硫酸二甲酯和硫化二甲酯在矿物酸或有机酸的存在下发生反应。三甲基硫酸甲酯的阴离子被酸转化为硫酸氢甲酯，硫酸氢甲酯又与过量的硫化二甲酯反应生成三甲基硫酸氢鎓。其结果是，硫酸二甲酯的两个甲基基团都转化为所需的三甲基锍盐，进而转化为甲烷二甲基锍；该过程由低沸点的硫化二甲酯介导，可以循环使用，而且副产品（K2SO4）比甲基硫酸钾更容易处理。
• Forrester, Julie; Jones, Ray V. H; Preston, Peter N., Journal of the Chemical Society. Perkin transactions I, 1993, # 17, p. 1937 - 1938
  作者：Forrester, Julie、Jones, Ray V. H、Preston, Peter N.、Simpson, Elisabeth S. C.

  DOI：——

  日期：——
• Synthesis and Biological Activity Evaluation of 1,2,3-Thiadiazole Derivatives as Potential Elicitors with Highly Systemic Acquired Resistance
  作者：Zhijin Fan、Zugui Shi、Haike Zhang、Xiufeng Liu、Lili Bao、Lin Ma、Xiang Zuo、Qinxiang Zheng、Na Mi

  DOI：10.1021/jf8031364

  日期：2009.5.27

  Elicitors provide a broad spectrum of systemic acquired resistance by altering the physical and physiological status of the host plants and, therefore, are among the most successful directions in modern pesticide development for plant protection. To develop a novel elicitor with highly systemic acquired resistance, two series of thiazole- and oxadiazole-containing thiadiazole derivatives were rationally designed and synthesized according to the principle of combination of bioactive substructures in this work. Their structures were characterized by (1)H nuclear magnetic resonance (NMR), infrared (IR), high-resolution mass spectrometry (HRMS), or elemental analysis. Their potential systemic acquired resistance as an elicitor was also evaluated; bioassay results indicated that, among the 23 compounds synthesized, three compounds, 10a, 10d, and 12b, displayed better systemic acquired resistance than the positive control, tiadinil, a commercialized 1,2,3-thiadiazole-based elicitor. In addition, three other compounds, 10f, 12c, and 12j, exhibited a certain degree of fungus growth inhibition in vitro or in vivo. Our results demonstrated that, in combination of bioactive substructures is an interesting exploration for novel pesticide development, thiazole- and oxadiazole-containing thiadiazole derivatives are potential elicitors with good systemic acquired resistance.
• Forrester, Julie; Jones, Ray V. H.; Preston, Peter N., Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2289 - 2292
  作者：Forrester, Julie、Jones, Ray V. H.、Preston, Peter N.、Simpson, Elizabeth S. C.

  DOI：——

  日期：——

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