乙基甲基酮肟 | 10341-59-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 乙基甲基酮肟
• 英文名称: (Z)-2-butanone oxime
• 英文别名: ethyl methyl ketoxime；methyl ethyl ketoxime；Z-butan-2-one oxime；Z-2-butanone oxime；butan-2-one (Z)-oxime；(anti-Methyl)-Butanon-oxim；Butanone oxime；(NZ)-N-butan-2-ylidenehydroxylamine
• CAS: 10341-59-0
• 化学式: C₄H₉NO
• 分子量: 87.1216
• InChiKey: WHIVNJATOVLWBW-PLNGDYQASA-N

物化性质

• 沸点：
  150-155 °C
• 密度：
  0.90±0.1 g/cm3(Predicted)
• 物理描述：
  Methyl ethyl ketoxime is a clear colorless liquid with a musty odor. (NTP, 1992)
• 颜色/状态：
  Liquid
• 熔点：
  -29.5 °C
• 闪点：
  138 °F (NTP, 1992)
• 溶解度：
  In water, 100,000 mg/L at 25 °C
• 蒸汽密度：
  3 (NTP, 1992) (Relative to Air)
• 蒸汽压力：
  1.06 mm Hg at 20 °C
• 分解：
  When heated to decomposition it emits toxic fumes of /oxides of nitrogen/.
• 折光率：
  Index of refraction = 1.4410 at 20 °C/D
• 解离常数：
  pKa = 12.45 at 25 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

代谢

物质/2-丁酮肟/可以在动物体内代谢为2-丁酮和羟基胺。

The substance /2-butanone oxime/ can be metabolized in vivo in animals to 2-butanone and hydroxylamine.

来源:Hazardous Substances Data Bank (HSDB)

代谢

甲基乙基酮肟在体内被广泛代谢，不会在组织中积累。给大鼠单次灌胃剂量为2.7、27或270 mg/kg时，主要转化为二氧化碳，大部分在给药后24小时内完成。静脉给药后，以百分比为基础排出的二氧化碳放射性比灌胃研究少，更多的给药剂量以尿液和挥发性物质形式排出。经皮给药后，排出的挥发性物质量显著大于灌胃或静脉给药。270 mg/kg的灌胃剂量可能导致代谢途径（s）饱和。有一些证据表明酮肟被代谢为酮，推测还有羟胺...

...Methyl ethyl ketoxime is extensively metabolized and does not accumulate in tissues. Single gavage doses of 2.7, 27, or 270 mg/kg administered to rats were primarily converted to carbon dioxide, mostly in the first 24 hours after dosing. After intravenous administration, less radioactivity on a percentage basis was excreted as carbon dioxide than in the gavage study, and more of the administered dose was excreted in urine and as volatiles. Following dermal administration, significantly greater amounts of volatiles were excreted than after gavage or intravenous administration. The 270 mg/kg gavage dose may result in saturation of a metabolic pathway(s). There is some evidence that the ketoxime is metabolized to the ketone and, presumably, hydroxylamine...

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

神经毒素 - 其他中枢神经系统神经毒素 高铁血红蛋白血症 - 血液中增加的高铁血红蛋白的存在；这种化合物被归类为次要的毒性效应 溶血性贫血 - 血红蛋白或红细胞数量减少。 皮肤致敏剂 - 能诱导皮肤发生过敏反应的制剂。

Neurotoxin - Other CNS neurotoxin Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect Hemolytic anemia - Decreased hemoglobin or number of red blood cells. Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 毒性数据

大鼠LC50 > 1350 ppm/4小时

LC50 (rat) > 1350 ppm/4hr

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩，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。如果患者呕吐，让患者向前倾或将其置于左侧（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，协助通气。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……。预期癫痫发作，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，如果患者能够吞咽、有强烈的干呕反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污染后，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：对于无意识、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D5W /SRP: "保持开放"，最小流量/。如果出现低血容量的迹象，使用0.9%的生理盐水（NS）或乳酸林格氏液。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……。 /Poisons A and 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 /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's 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)

吸收、分配和排泄

在妊娠第14天，给怀孕小鼠单次口服14(C)-2丁酮肟。此外，一只雄性小鼠也被给予单次口服(14)C-2-丁酮肟。看来该物质通过口服途径被迅速吸收，并完整地分布到全身。整个研究期间尿液和胆汁中含有的放射性活动显著。肠道活动最小。这表明该物质主要通过肾脏排泄。

Pregnant mice were administered a single oral dose of 14(C)-2 butanone oxime on day 14 of gestation. In addition, a male mouse was administered a single oral dose of (14)C-2-butanone oxime. It appears that the substance is rapidly absorbed via the oral route, and distributed intact through the body. Urine and bile contained significant activity throughout the study. Intestinal activity was minimal. This suggests that the substance is primarily excreted via the kidneys.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

14(C)-甲基乙基酮肟（MEKO）在雄性F344大鼠体内的处置情况通过口服、静脉注射和皮肤给药后进行了确定。口服剂量为2.7、27和270 mg/kg的药物主要以CO2形式排出（71-49%），随着剂量的增加，排出百分比逐渐降低。尿液中（13-26%）和挥发性物质中（5-18%）的排出量随着剂量的增加而增加。72小时内，大约有5-6%的剂量残留在主要组织中。静脉注射2.7 mg/kg的剂量也主要作为CO2排出（48.8%），尿液中和作为呼出气体的排出分别占21.4%和11.4%。大约7%的放射性物质在72小时后仍留在组织中。皮肤给药后，2.7和270 mg/kg剂量中分别有13%和26%被吸收。在放入代谢笼之前，剂量部位挥发的物质可能是吸收率低的原因。MEKO被生物转化为至少五种极性代谢物，这些代谢物只能通过阴离子交换色谱部分分离。与葡萄糖苷酸酶孵育，但不与磺酸酯酶孵育，改变了尿液中代谢物的谱。甲基乙基酮是挥发性物质中的主要成分。

The disposition of 14(C)-methyl ethyl ketoxime (MEKO) was determined in the male F344 rat following oral, iv and dermal administration. Oral doses of 2.7, 27 and 270 mg/kg were primarily excreted as CO2 (71-49%) in decreasing percentage as the dose increased. Excretion in urine (13-26%) and as volatiles (5-18%) increased as the dose increased. Five to 6% of the dose remained in the major tissues after 72 hr. An iv dose of 2.7 mg/kg was also principally excreted as CO2 (48.8%) with excretion in urine and as expired volatiles accounting for 21.4 and 11.4%, respectively. About 7% of the administered radioactivity remained in the tissues after 72 hr. Following dermal administration, 13 and 26% of a 2.7 and 270 mg/kg dose, respectively, were absorbed. Volatilization from the dose site prior to placement in the metabolism cage may account for the low absorption. MEKO was biotransformed to at least five polar metabolites that could only be partially resolved by anion exchange chromatography. Incubation with glucuronidase, but not sulphatase, changed the urinary metabolic profile. Methyl ethyl ketone was a major component in the volatiles.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

甲基乙基酮肟在体内被广泛代谢，不会在组织中积累。给大鼠单次灌胃剂量为2.7、27或270毫克/千克时，主要转化为二氧化碳，大部分在给药后的前24小时内。静脉给药后，以百分比为基础排泄的二氧化碳放射性低于灌胃研究，更多的给药剂量以尿液和挥发性物质形式排出。经皮给药后，排出的挥发性物质量显著大于灌胃或静脉给药。270毫克/千克的灌胃剂量可能导致代谢途径（s）饱和。有证据表明酮肟被代谢为酮，可能还有羟胺...

...Methyl ethyl ketoxime is extensively metabolized and does not accumulate in tissues. Single gavage doses of 2.7, 27, or 270 mg/kg administered to rats were primarily converted to carbon dioxide, mostly in the first 24 hours after dosing. After intravenous administration, less radioactivity on a percentage basis was excreted as carbon dioxide than in the gavage study, and more of the administered dose was excreted in urine and as volatiles. Following dermal administration, significantly greater amounts of volatiles were excreted than after gavage or intravenous administration. The 270 mg/kg gavage dose may result in saturation of a metabolic pathway(s). There is some evidence that the ketoxime is metabolized to the ketone and, presumably, hydroxylamine...

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  乙基甲基酮肟 在 盐酸 、 乙酰氯 作用下， 生成 2,4,5-三甲基恶唑
  参考文献：
  名称：

  A new synthesis of oxazoles

  摘要：

  DOI：

  10.1016/s0040-4039(00)92606-6
• 作为产物：
  描述：

  丁酮 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 乙基甲基酮肟
  参考文献：
  名称：

  含喹喔啉部分肟醚衍生物的合成、生物学评价和计算机研究

  摘要：

  摘要 在这项研究中，描述了含有氨基环状残基的O -肟醚的合成。芳族酮的肟化之后是与环氧氯丙烷的O-烷基化反应，产生相应的O-肟醚加合物。o-苯二胺与O-肟醚加合物的环化导致合成新的喹喔啉化合物类似物。评估了所有化合物对大肠杆菌ATTC 35218 和金黄色葡萄球菌的体外抗菌活性ATCC 6538 标准菌株，并与四环素和青霉素作为参考药物进行比较。此外，实施了合成化合物的分子对接研究。对接研究的结果表明，具有小取代（如甲基和乙基）的衍生物表现出最高的亲和力并与测试细菌的活性位点结合（大肠杆菌Mur B（PDB ID：2Q85）和金黄色葡萄球菌促旋酶 B（PDB ID: 3G75)) 这导致了这些化合物更好的生物学效应。

  DOI：

  10.1134/s1068162023010326

文献信息

• Synthesis of Highly Substituted Pyrroles via Nucleophilic Catalysis
  作者：Simbarashe Ngwerume、Jason E. Camp

  DOI：10.1021/jo1011448

  日期：2010.9.17

  tri-, and tetrasubstituted pyrroles is described. This regioselective one-pot method relies on nucleophilic catalysis of the intermolecular addition of oximes to activated alkynes and thermal rearrangement of the in situ generated O-vinyl oximes to form pyrroles that contain a functional group handle at the C3/C4 position.

  描述了提供二，三和四取代吡咯的简明合成的亲核催化方法。这种区域选择性的一锅法依赖于在分子间加成肟到活化的炔烃上的亲核催化和原位生成的O-乙烯基肟的热重排形成吡咯，这些吡咯在C3 / C4位置上含有一个官能团。
• A Facile Beckmann Rearrangement of Oximes with AlCl₃in the Solid State
  作者：M. Ghiaci、G. Hassan Imanzadeh

  DOI：10.1080/00397919808007044

  日期：1998.6

  Abstract A facile and efficient synthetic procedure, for Beckmann rearrangement of oximes with AlCl3 in the absence of solvent is developed. We have been able to convert cyclohexanone oxime to ϵ-caprolactam in a quantitative yield.

  摘要 开发了一种简便有效的合成方法，用于在没有溶剂的情况下用 AlCl3 进行肟的贝克曼重排。我们已经能够以定量产率将环己酮肟转化为 ε-己内酰胺。
• The oxime rearrangement cyclization. Alkenyl, styryl and vinyl chloride terminators in the synthesis of Δ1-pyrrolines
  作者：Robert E. Gawley、Enrico J. Termine

  DOI：10.1016/s0040-4039(00)86816-1

  日期：1982.1

  Functionalized γ,δ-unsaturated oximes, constructed by regiospecific alkylation of appropriate oximes, may be rearranged and cyclized to Δ1-pyrrolines in good yield.

  官能γ，δ不饱和肟，通过适当的肟区域专一的烷基化构造，可以被重新安排和环化，Δ 1以良好的收率-pyrrolines。
• The Mild Synthesis of Oxime Phosphates by Atherton–Todd Reaction
  作者：Ming Shu Wu、Xiang Zhu Zhang

  DOI：10.3184/030823407x196944

  日期：2007.3

  The oximes (1a–i) on reaction with diethyl phosphonates (2) in the presence of triethylamine using chlorocarbons as solvents mildly provide oxime phosphates (3a–i) in good yields and have no the Beckmann rearrangement.

  在三乙胺存在下，使用氯烃作为溶剂，肟 (1a-i) 与膦酸二乙酯 (2) 反应温和地以良好的收率提供肟磷酸酯 (3a-i)，并且没有贝克曼重排。
• REGIOSELECTIVE SULFENYLATION OF OXIME DIANIONS. A NOVEL AND USEFUL METHOD FOR THE REGIOSELECTIVE RING CLEAVAGE
  作者：Kunio Hiroi、Masahiko Otsuka、Shuko Sato

  DOI：10.1246/cl.1985.1907

  日期：1985.12.5

  Treatment of the dianions of cyclic ketoximes with diphenyl disulfide underwent a regioselective sulfenylation at the syn α-carbons. Regioselective alkylation of cyclic ketoxime dianions, followed by sulfenylation with diphenyl disulfide, produced α-alkyl-α′-phenylsulfenyl ketoximes. A Beckmann fragmentation of these sulfenylated ketoximes gave ring cleaved products. This procedure provides a synthetically

  用二苯基二硫化物处理环状酮肟的二价阴离子在顺α-碳上发生区域选择性亚磺酰化。环状酮肟双阴离子的区域选择性烷基化，然后用二苯基二硫化物进行亚磺酰化，产生 α-烷基-α'-苯基亚磺酰基酮肟。这些磺基化酮肟的贝克曼断裂得到环裂解产物。该过程为区域选择性环裂解提供了一种综合有用的方法，保留了有价值的功能。

表征谱图