1-phenylbutan-2-one oxime | 5368-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-phenylbutan-2-one oxime
• 英文别名: N-(1-Phenylbutan-2-ylidene)hydroxylamine；N-(1-phenylbutan-2-ylidene)hydroxylamine
• CAS: 5368-18-3
• 化学式: C₁₀H₁₃NO
• mdl: MFCD23714136
• 分子量: 163.219
• InChiKey: UBQQQMMMFFWYGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  1-phenylbutan-2-one oxime 在 copper diacetate 、 potassium carbonate 、 2,6-双(4,5-二氢噁唑-2-基)吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 1-benzyl-3-ethylisoquinoline
  参考文献：
  名称：

  Copper‐Catalyzed Aza‐Sonogashira Cross‐Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles

  摘要：

  AbstractNitrogen‐substituted alkynes, such as ynamines and ynamides, are versatile synthetic building blocks. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high synthetic potential. However, their chemical reactivity remains unexplored owing mainly to the lack of synthetic accessibility. We report herein a versatile copper‐catalyzed synthesis of ynimines from readily available O‐acetyl ketoximes and terminal alkynes. A wide range of O‐acetyl ketoximes derived from diaryl ketones, aryl alkyl ketones and dialkyl ketones underwent cross‐coupling with a diverse set of terminal alkynes to afford the ynimines in good to excellent yields. An unprecedented [5+1] heteroannulation reaction exploiting the reactivity of the ynimine generated in situ was subsequently developed for the synthesis of medicinally important heterocycles, including isoquinolines, azaindoles, azabenzofurans, azabenzothiophenes and carbolines.

  DOI：

  10.1002/anie.202110901
• 作为产物：
  描述：

  苯甲醛 在 硫酸 、 正丁胺 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 生成 1-phenylbutan-2-one oxime
  参考文献：
  名称：

  Wessling, Michael; Schaefer, Hans J., Chemische Berichte, 1991, vol. 124, # 10, p. 2303 - 2306

  摘要：

  DOI：

文献信息

• Aziridine formation by lithium aluminum hydride reduction of oximes
  作者：K. Kotera、S. Miyazaki、H. Takahashi、T. Okada、K. Kitahonoki

  DOI：10.1016/s0040-4020(01)92001-0

  日期：1968.1

  The azirine formation by LAH reduction of oximes has been extended to several types, such asandThe result was satisfactory to generalization of this reaction.

  通过LAH还原肟形成的叠氮基已扩展为多种类型，例如和，其结果对于该反应的一般化是令人满意的。
• Laccase-catalysed biotransformation of collismycin derivatives. A novel enzymatic approach for the cleavage of oximes
  作者：Javier González-Sabín、Nicolás Ríos-Lombardía、Ignacio García、Natalia M. Vior、Alfredo F. Braña、Carmen Méndez、José A. Salas、Francisco Morís

  DOI：10.1039/c5gc02220g

  日期：——

  An unprecedented and eco-friendly method for the deprotection of oximes with a laccase/tempo system was developed.

  一种利用漆酶/TEMPO系统去保护肟的前所未有且环保的方法被开发出来。
• Carbamoyl Anion Addition to Azirines
  作者：Michael J. Kerner、Christian A. Kuttruff、Maxim Chevliakov、Frederic G. Buono、Donghong A. Gao、Mariusz Krawiec、Carl A. Busacca、Chris H. Senanayake、Peter Wipf、Jonathan T. Reeves

  DOI：10.1021/acs.orglett.1c01334

  日期：2021.6.4

  The addition of carbamoyl anions to azirines affords synthetically useful 2-aziridinyl amide building blocks. The reaction scope was explored with respect to both formamide and azirine, and the addition was found to be highly diastereoselective. A one-pot conversion of a ketoxime to an aziridinyl amide was demonstrated. The method was employed to incorporate an aziridine residue into a dipeptide segment

  向氮丙啶添加氨基甲酰基阴离子可提供合成有用的 2-氮丙啶酰胺结构单元。研究了甲酰胺和氮丙啶的反应范围，发现添加具有高度的非对映选择性。证明了酮肟到氮丙啶酰胺的一锅法转化。该方法用于将氮丙啶残基并入二肽片段中。
• N6-SUBSTITUTED ADENOSINE DERIVATIVES AND N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
  申请人：Shi Jiangong

  公开号：US20130045942A1

  公开（公告）日：2013-02-21

  The present invention provides N 6 -substituted adenosine derivatives and N 6 -substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.

  本发明提供了N6-取代腺苷衍生物和N6-取代腺嘌呤衍生物，其制备方法，包括上述化合物的药物组合物，以及这些化合物在制造治疗失眠、惊厥、癫痫和帕金森病的药物和保健产品以及预防和治疗痴呆症中的用途。
• Regioselective Transition Metal-Free Catalytic Ring Opening of 2<i>H</i>-Azirines by Phenols and Naphthols; One-Pot Access to Benzo- and Naphthofurans
  作者：Arnab Roy、Subrata Biswas、Surajit Duari、Srabani Maity、Abhishek Kumar Mishra、Aguinaldo R. de Souza、Asma M. Elsharif、Nelson H. Morgon、Srijit Biswas

  DOI：10.1021/acs.joc.3c01266

  日期：2023.11.17

  naphthofuran derivatives are synthesized from readily available phenols and naphthols. Regioselective ring openings of 2H-azirine followed by in situ aromatization using a catalytic amount of Brønsted acid have established the novelty of the methodology. The involvement of a series of 2H-azirines with a variety of phenols, 1-naphthols, and 2-naphthols showed the generality of the protocol. In-depth

  苯并呋喃和萘并呋喃衍生物是由容易获得的酚和萘酚合成的。 2 H-氮丙啶的区域选择性开环，然后使用催化量的布朗斯台德酸进行原位芳构化，确立了该方法的新颖性。一系列 2 H-氮丙啶与各种酚、1-萘酚和 2-萘酚的参与显示了该方案的通用性。深入的密度泛函理论计算揭示了模型反应的中间体和过渡态能量的反应机理。还通过计算机建模提出了该机制的替代途径。