p-menthan-3-one oxime | 19096-86-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: p-menthan-3-one oxime
• 英文别名: p-Menthan-3-on-oxim；Menthon-oxim；2-isopropyl-5-methyl-cyclohexane-1-one-oxime；N-(5-methyl-2-propan-2-ylcyclohexylidene)hydroxylamine
• CAS: 19096-86-7
• 化学式: C₁₀H₁₉NO
• mdl: MFCD00860044
• 分子量: 169.267
• InChiKey: XJKYDNDJFRDNHX-UHFFFAOYSA-N

物化性质

• 熔点：
  59 °C
• 沸点：
  257.1±9.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)
• LogP：
  2.704 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  p-menthan-3-one oxime 在 2-碘酰苯甲酸 、 β-环糊精 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 以82%的产率得到5-甲基-2-异丙基环己酮
  参考文献：
  名称：

  Deoximation of Oximes with 2-Iodylbenzoic Acid in Water in the Presence of β-Cyclodextrin

  摘要：

  在β-环糊精存在下，各种醛和酮的肟可以在室温下，在水中用2-碘苯甲酸以令人瞩目的产率转化为相应的羰基化合物。

  DOI：

  10.1055/s-2003-41448
• 作为产物：
  描述：

  5-甲基-2-异丙基环己酮 在 sodium hydroxide 、 盐酸羟胺 作用下， 生成 p-menthan-3-one oxime
  参考文献：
  名称：

  手性固定相上外消旋酮的肟3,5-二硝基苯基氨基甲酸酯的液相色谱拆分

  摘要：

  环状和无环手性酮已被解析为在（S）-1-（6,7-二乙基-1-萘基）异丁胺衍生的手性固定相上的肟3,5-二硝基苯基氨基甲酸酯。

  DOI：

  10.1016/s0040-4039(00)80594-8

文献信息

• Selective Synthesis of Primary Anilines from Cyclohexanone Oximes by the Concerted Catalysis of a Mg–Al Layered Double Hydroxide Supported Pd Catalyst
  作者：Xiongjie Jin、Yu Koizumi、Kazuya Yamaguchi、Kyoko Nozaki、Noritaka Mizuno

  DOI：10.1021/jacs.7b07347

  日期：2017.10.4

  selective conversion of cyclohexanone oximes to primary anilines would be a good complement to the classical synthetic methods for primary anilines, which utilize arenes as the starting materials, there have been no general and efficient methods for the conversion of cyclohexanone oximes to primary anilines until now. In this study, we have successfully realized the efficient conversion of cyclohexanone

  尽管环己酮肟选择性转化为伯苯胺将是对以芳烃为起始原料的伯苯胺经典合成方法的一个很好的补充，但一直没有通用和有效的方法将环己酮肟转化为伯苯胺，直到现在。在这项研究中，我们通过使用 Mg-Al 层状双氢氧化物负载的 Pd 催化剂 (Pd(OH)x/LDH) 在配体-、添加剂-和氢-受体-下成功地实现了环己酮肟向伯苯胺的有效转化。免费条件。环己酮肟和环己烯酮肟的底物范围非常广泛，以高产率和高选择性得到相应的伯苯胺（17 个实施例，产率 75% 至 >99%）。可以使用减少量的催化剂 (0.2 mol%) 放大反应（克级）。此外，直接从环己酮和羟胺一锅法合成伯苯胺也很成功（五个例子，66-99% 的产率）。该催化剂本质上是非均相的，该催化剂可重复用于环己酮肟转化为苯胺至少五次，同时保持其高催化性能。动力学研究和几个对照实验表明，本催化剂体系的高活性和选择性归因于碱性 LDH 载体和 LDH 上活性
• Europium(III) Triflate-Catalyzed Trofimov Synthesis of Polyfunctionalized Pyrroles
  作者：Sridhar Madabhushi、Venkata Sairam Vangipuram、Kishore Kumar Reddy Mallu、Narsaiah Chinthala、China Ramanaiah Beeram

  DOI：10.1002/adsc.201200036

  日期：2012.5.21

  The synthesis of polyfunctionalized pyrroles by reaction of a ketoxime with dimethyl acetylenedicarboxylate using europium(III) triflate as the catalyst is described.

  描述了通过使用三氟甲磺酸euro（III）作为催化剂，使酮肟与乙炔二甲酸二甲酯反应来合成多官能吡咯。
• Metal-assisted coupling of oximes and nitriles: a synthetic, structural and theoretical study
  作者：Maxim L. Kuznetsov、Nadezhda A. Bokach、Vadim Yu. Kukushkin、Tapani Pakkanen、Gabriele Wagner、Armando J. L. Pombeiro

  DOI：10.1039/b006168i

  日期：——

  Chlorination of [Ph3PCH2Ph][PtCl3(EtCN)], obtained from the reaction of [PtCl2(EtCN)2] with [Ph3PCH2Ph]Cl, formed the platinum(IV) complex [Ph3PCH2Ph][PtCl5(EtCN)] which, at ambient temperature and both in solution and in the solid phase, hydrolyses to the ammonia compound [Ph3PCH2Ph][PtCl5(NH3)] and undergoes nucleophilic addition by ketoximes or amidoxime HONCR1R2 [R1R2 = Me2, C4H8, C5H10, C9H16, C9H18 or Ph(NH2)] to give the corresponding iminoacylated product [Ph3PCH2Ph][PtCl5HNC(Et)ONCR1R2}]. All compounds were characterized by elemental analyses, FAB mass spectrometry, IR and 1H, 13C-1H}, 31P-1H} and 195Pt NMR spectroscopies. A crystal structure determination of [Ph3PCH2Ph][PtCl5NHC(Et)ONC(C9H16)}] disclosed amidine one-end rather than the N,N-bidentate co-ordination mode of the N-donor ligand. The iminoacylation by oximes was investigated by ab initio methods (at RHF level using quasi-relativistic pseudopotentials for platinum) for [PtCl5(NCMe)]− which were also applied to the related neutral platinum(IV) [PtCl4(NCMe)2] and platinum(II) [PtCl2(NCMe)2] complexes. The calculations included geometry optimization of the starting and final complexes, location of possible transition states for the reaction discussed and intrinsic reaction coordinate calculations for one reaction. The results obtained provided an interpretation, on the basis of kinetic (activation energies) and thermodynamic (reaction energies) effects, for the order of reactivity observed [neutral PtIV > anionic PtIV > neutral PtII] and indicated that a mechanism based on nucleophilic addition of the protic nucleophile (undeprotonated oxime), to form a transition state with a four-membered NCOH ring, is energetically favoured relative to the alternative one involving prior deprotonation of the oxime, unless base-catalysed conditions are operating.

  由[PtCl2(EtCN)2]与[Ph3PCH2Ph]Cl反应得到的[Ph3PCH2Ph][PtCl3(EtCN)]氯化反应生成了铂(IV)络合物[Ph3PCH2Ph][PtCl5(EtCN)]、在常温下，该复合物在溶液和固相中都会水解为氨化合物 [Ph3PCH2Ph][PtCl5(NH3)]，并与酮肟或脒肟 HONCR1R2 [R1R2 = Me2、C4H8、C5H10、C9H16、C9H18 或 Ph(NH2)]发生亲核加成反应，生成相应的亚氨基酰化产物 [Ph3PCH2Ph][PtCl5HNC(Et)ONCR1R2}]。所有化合物都通过元素分析、FAB 质谱、红外光谱和 1H、13C-1H}、31P-1H} 和 195Pt NMR 光谱进行了表征。[Ph3PCH2Ph][PtCl5NHC(Et)ONC(C9H16)}]的晶体结构测定结果表明，N-供体配体的一端为脒基，而不是 N,N-配位模式。我们采用 ab initio 方法（在 RHF 水平上使用铂的准相对论假势）研究了[PtCl5(NCMe)]--肟的亚氨基酰化作用，该方法也适用于相关的中性铂（IV）[PtCl4(NCMe)2]和铂（II）[PtCl2(NCMe)2]配合物。计算包括起始和最终配合物的几何优化、所讨论反应的可能过渡态的位置以及一个反应的内在反应坐标计算。所获得的结果在动力学（活化能）和热力学（反应能）效应的基础上解释了所观察到的反应性顺序[中性 PtIV > 阴离子 PtIV > 中性 PtII]，并表明除非在碱催化条件下，否则基于亲核体（未去质子化的肟）亲核加成以形成具有四元 NCOH 环的过渡态的机理在能量上要优于涉及肟事先去质子化的替代机理。
• Clinico-Histopathological Concordance in Leprosy
  作者：Premala Anthony Singh、Ranjan Agarwal、Vatsala Misra、Suresh Chand Gupta、Ashok Kumar Bajaj

  DOI：10.1177/004947550003000418

  日期：2000.10

  Histopathological examination of biopsies from 111 patients with clinically diagnosed leprosy was carried out in order to observe the clinico-histopathological correlation. Clinical diagnosis was based on Ridley and Jopling (R-J) classification and World Health Organization (WHO) classification. The concordance rate between the two clinical classifications was 73.8%. Sections were stained with haematoxylin and eosin (H&E) and Ziehl-Neelsen's (Z-N) stains. The histological classification was as per the R-J criteria. Skin biopsy showed evidence of leprosy in 104 cases (93.69%). Overall concordance was observed in 58.6% (R-J) and 85.6% (WHO classification). The kappa test, when applied, showed significant agreement between clinical and histopathological diagnosis ( z=11.775; P<0.001). Individual subtypes showed variable concordance rates — which were again higher using WHO classification. When some of the subtypes were combined, the concordance rate was 83.02% for TT+BT; 72.58% for BT+BB+BL; 73.91% for BL+LL; 80.77% for BL+HL and 100% for LL+HL. (See Introduction for definitions of abbreviations.

  The present study highlights the importance of histopathological examination for exact subtyping of leprosy, so as to facilitate the institution of accurate mode of therapy and regular follow-up of patients to prevent undesirable complications.

  对111名临床诊断为麻风的患者进行了组织病理学检查，以观察临床和组织病理学之间的相关性。临床诊断基于Ridley和Jopling（R-J）分类和世界卫生组织（WHO）分类。两种临床分类之间的一致性率为73.8％。切片经过苏木精和伊红（H&E）染色和Ziehl-Neelsen（Z-N）染色。组织学分类按照R-J标准进行。皮肤活检显示104例（93.69％）有麻风病迹象。总体一致性率为58.6％（R-J）和85.6％（WHO分类）。应用kappa检验时，临床和组织病理诊断之间显示有显著的一致性（z = 11.775; P<0.001）。各个亚型显示不同的一致性率-再次使用WHO分类时一致性率更高。当一些亚型组合时，TT + BT的一致性率为83.02％；BT + BB + BL的一致性率为72.58％；BL + LL的一致性率为73.91％；BL + HL的一致性率为80.77％；LL + HL的一致性率为100％。 （有关缩写定义，请参见介绍。） 本研究凸显了组织病理学检查对于确切分型麻风的重要性，以便实施准确的治疗方式和对患者进行常规随访，以防止不良并发症的发生。
• Structural Diversity Design, Synthesis, and Insecticidal Activity Analysis of Ester-Containing Isoxazoline Derivatives Acting on the GABA Receptor
  作者：Caixia Zhang、Hanxiao Yuan、Yuge Hu、Xiuhuan Li、Yanqing Gao、Zhiqing Ma、Peng Lei

  DOI：10.1021/acs.jafc.2c07910

  日期：——

  targeting the γ-aminobutyric acid (GABA) receptor, two series of novel isoxazoline derivatives containing sulfonic and carboxylic esters were designed and synthesized. Their insecticidal activities against Plutella xylostella, Mythimna separata, and Aedes aegypti larvae and their structure–activity relationship were investigated. The sulfonate-containing isoxazoline derivatives (10k–q) exhibited promising

  为了探索针对γ-氨基丁酸（GABA）受体的杀虫剂，设计并合成了两个系列的新型含磺酸酯和羧酸酯的异恶唑啉衍生物。研究了它们对小菜蛾、粘虫和埃及伊蚊幼虫的杀虫活性及其构效关系。含磺酸盐的异恶唑啉衍生物（ 10k-q ）对三种昆虫幼虫表现出良好的杀虫活性。化合物10o对小菜蛾、分离小菜蛾和埃及伊蚊幼虫表现出优异的活性，48 h时的LC 50值分别为8.32、5.23和0.35 μg/mL，优于或接近阿维菌素。此外，化合物10o对M. separata表现出比阿维菌素更快的杀虫效果。通过分子对接、理论计算以及谷氨酸脱羧酶和谷氨酸丙酮转氨酶活性测定，初步验证了10o的作用模式。化合物10o是一种作用于GABA受体的新型杀虫候选药物，可以指导异恶唑啉杀虫剂的发现。