1-(2-methoxyphenyl)propan-2-one oxime | 43021-97-2

• 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-(2-methoxyphenyl)propan-2-one oxime
• 英文别名: N-[1-(2-methoxyphenyl)propan-2-ylidene]hydroxylamine
• CAS: 43021-97-2
• 化学式: C₁₀H₁₃NO₂
• mdl: MFCD01076408
• 分子量: 179.219
• InChiKey: GBJMYMLSKUVGCD-UHFFFAOYSA-N

物化性质

• 沸点：
  317.0±25.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 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：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-methoxyphenyl)propan-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-5-methoxy-3-methylisoquinoline
  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：

  邻甲氧基苯丙酮 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 为溶剂， 生成 1-(2-methoxyphenyl)propan-2-one oxime
  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

文献信息

• Practical Syntheses of N-Acetyl (E)-β-Arylenamides
  作者：Wenjun Tang、Zhihua Cai、Guodu Liu、Guangjun Jiao、Chris Senanayake

  DOI：10.1055/s-0033-1339976

  日期：——

  facile and practical method for the preparation of (E)-β-arylenamides [(E)-N-(1-arylprop-1-en-2-yl]acetamides] has been developed by reductive acetylation of the corresponding oximes with iron(II) acetate as the reducing reagent. Employment of hexamethylphosphoramide as the solvent was found to be critical for the high E/Z selectivity. The methodology has been applied in efficient syntheses of a key

  摘要 通过用铁还原相应的肟，开发了一种简便实用的制备（E）-β-芳基酰胺[（E）-N-（1-芳基丙-1-烯-2-基]乙酰胺]的方法（II）乙酸盐作为还原剂发现使用六甲基磷酰胺作为溶剂对高E / Z选择性至关重要，该方法已用于通过不对称氢化有效合成坦索罗辛的关键手性中间体。 通过用铁还原相应的肟，开发了一种简便实用的制备（E）-β-芳基酰胺[（E）-N-（1-芳基丙-1-烯-2-基]乙酰胺]的方法（II）乙酸盐作为还原剂发现使用六甲基磷酰胺作为溶剂对高E / Z选择性至关重要，该方法已用于通过不对称氢化有效合成坦索罗辛的关键手性中间体。
• Isolation and Reactions of Imidoyl Fluorides Generated from Oxime Using the Diethylaminosulfur Trifluoride/Tetrahydrofuran (DAST–THF) System
  作者：Yipu Lu、Akitomo Kasahara、Tadashi Hyodo、Kazuaki Ohara、Kentaro Yamaguchi、Yuko Otani、Tomohiko Ohwada

  DOI：10.1021/acs.orglett.3c01063

  日期：2023.5.19

  mild diethylaminosulfur trifluoride/tetrahydrofuran (DAST–THF) system affords imidoyl fluorides. These compounds were isolated, and their structures were confirmed by X-ray single-crystal structure analysis. Reaction of imidoyl fluorides with various nucleophiles efficiently afforded amides, amidines, thioamides, and amine derivatives in high yields. Furthermore, one-pot reaction of in situ generated

  用相对温和的二乙氨基三氟化硫/四氢呋喃 (DAST–THF) 系统氟化肟，得到亚氨基氟化物。这些化合物被分离出来，并通过 X 射线单晶结构分析确定了它们的结构。亚氨基氟化物与各种亲核试剂的反应有效地以高产率提供酰胺、脒、硫代酰胺和胺衍生物。此外，由肟原位生成亚氨基氟化物的一锅法反应也适用于这些产品的高效合成。肟立体化学和酸不稳定保护基在该系统中保持完整。
• Copper‐Catalyzed Aza‐Sonogashira Cross‐Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles
  作者：Rémi Lavernhe、Rubén O. Torres‐Ochoa、Qian Wang、Jieping Zhu

  DOI：10.1002/anie.202110901

  日期：2021.11.2

  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.