1,3-diphenylpropan-2-one O-acetyl oxime | 19689-93-1

• 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: 1,3-diphenylpropan-2-one O-acetyl oxime
• 英文别名: 1,3-Diphenylpropanone oxime O-acetate；O-Acetyl-dibenzylketoxim；(1,3-Diphenylpropan-2-ylideneamino) acetate
• CAS: 19689-93-1
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: PJWXZIHFDQUDDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-diphenylpropan-2-one O-acetyl oxime 在 diiron nonacarbonyl 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以82%的产率得到二苄基甲酮
  参考文献：
  名称：

  用九羰基二铁或五羰基二铁脱肟O-乙酸酯、肟和肟醚。N-O 键断裂的电子效应

  摘要：

  [Fe2(CO)9] 或 [Fe(CO)5] 与肟 O-乙酸酯、肟和肟醚在光辐射或热条件下的反应进行脱肟反应得到相应的酮。发现肟 O-乙酸酯是这些化合物中反应性最强的一类。提出的机制涉及 [Fe(CO)4] 物质与肟基团的氮原子的初始络合，以及随后的 N-O 键断裂以产生亚氨基络合物。然后，酰亚胺复合物可以通过质子介质中的亚胺中间体塌缩成相应的酮。

  DOI：

  10.1246/bcsj.57.3357
• 作为产物：
  描述：

  二苄基甲酮 在 盐酸羟胺 、 sodium acetate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1,3-diphenylpropan-2-one O-acetyl 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

• Palladium-catalyzed Heck-type reaction of oximes with allylic alcohols: synthesis of pyridines and azafluorenones
  作者：Meifang Zheng、Pengquan Chen、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c5cc06958k

  日期：——

  We describe herein a palladium-catalyzed Heck-type reaction of O-acetyl ketoximes and allylic alcohols to pyridines. This protocol allows robust synthesis of pyridines and azafluorenones in good to excellent yields with...

  我们在本文中描述了O-乙酰基酮肟和烯丙基醇对吡啶的钯催化的Heck型反应。该方案可实现吡啶和氮杂氟烯酮的稳健合成，产率高至极好，且...
• RUBBER COMPOSITION AND VULCANIZATION AID
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20170130028A1

  公开（公告）日：2017-05-11

  A rubber composition comprising a compound having one or more groups represented by formula (X) and a rubber component is provided. wherein ring W 1 represents a cyclic group having at least one selected from the group consisting of —C(═O)— and —C(═S)—; N 10 represents a nitrogen atom; the at least one selected from the group consisting of —C(═O)— and —C(═S)— in the ring W 1 and N 10 are conjugated; and Z 1 represents —O— or —S—.

  提供一种橡胶组合物，包括具有一个或多个由式（X）表示的基团和橡胶组分，其中环W1代表具有至少一种从羰基和硫代基组成的群中选出的环；N10代表氮原子；环W1和N10中所选的至少一种从羰基和硫代基组成的群是共轭的；Z1代表氧或硫。
• Rubber composition and vulcanization aid
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US10287419B2

  公开（公告）日：2019-05-14

  A rubber composition comprising a compound having one or more groups represented by formula (X) and a rubber component is provided. wherein ring W1 represents a cyclic group having at least one selected from the group consisting of —C(═O)— and —C(═S)—; N10 represents a nitrogen atom; the at least one selected from the group consisting of —C(═O)— and —C(═S)— in the ring W1 and N10 are conjugated; and Z1 represents —O— or —S—.

  提供了一种橡胶组合物，该组合物由具有一个或多个由式 (X) 表示的基团的化合物和橡胶成分组成。 其中环 W1 代表环状基团，该环状基团至少有一个选自-C(═O)- 和-C(═S)- 组成的组；N10 代表氮原子；环 W1 和 N10 中至少一个选自-C(═O)- 和-C(═S)- 组成的组是共轭的；Z1 代表-O- 或-S-。
• Dicobaltoctacarbonyl-Mediated Deoximation
  作者：Chisato Mukai

  DOI：10.1055/s-1999-3603

  日期：1999.11
• Cu-Catalyzed Three-Component Cascade Annulation Reaction: An Entry to Functionalized Pyridines
  作者：Huanfeng Jiang、Jidan Yang、Xiaodong Tang、Jianxiao Li、Wanqing Wu

  DOI：10.1021/acs.joc.5b01621

  日期：2015.9.4

  A concise copper-catalyzed N-O bond cleavage/C-C/C-N bond formation procedure has been described for the synthesis of multisubstituted pyridines. Various oxime acetates, activated methylene compounds, and a wide range of aldehydes bearing aryl, heteroaryl, vinyl, and trifluoromethyl groups were employed to provide the tri- or tetrasubstituted pyridines with flexible substitution patterns. Moreover, this method features inexpensive catalysts, no need for extra oxidant, and high step-enconomy, which make it pratical and attractive.