2,4,6-trimethyl-benzoic acid 2-oxo-2-phenyl-ethyl ester | 63370-05-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-trimethyl-benzoic acid 2-oxo-2-phenyl-ethyl ester
• 英文别名: phenacyl 2,4,6-trimethylbenzoate；2,4,6-Trimethyl-benzoesaeure-phenacylester；2,4,6-Trimethylbenzoesaeure-phenacylester
• CAS: 63370-05-8
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: CCGOTIRXEDNTFB-UHFFFAOYSA-N

物化性质

• 熔点：
  80-81 °C(Solv: ligroine (8032-32-4))
• 沸点：
  437.1±33.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4,6-trimethyl-benzoic acid 2-oxo-2-phenyl-ethyl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 四甲基乙二胺 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 37.0h， 生成
  参考文献：
  名称：

  Enantioselective Synthesis of α-Tertiary Hydroxyaldehydes by Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates

  摘要：

  Chiral alpha-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chemistry. Herein, we report the first examples of a catalytic asymmetric protocol for the synthesis of such compounds from readily available alpha-halo or alpha-hydroxy ketones or enol silyl ethers with excellent yields and nantioselectivity. Its synthetic utility is demonstrated in the short, efficient formal synthesis of (S)-oxybutynin. In this process, the chiral ligand controls the regioselectivity as well as the enantioselectivity.

  DOI：

  10.1021/ja067342a
• 作为产物：
  描述：

  2-溴苯乙酮 以98%的产率得到
  参考文献：
  名称：

  THORAT, M.;MANE, R.;JAGDALE, M.;SALUNKHE, M., ORG. PREP. AND PROCED. INT., 1986, 18, N 3, 203-205

  摘要：

  DOI：

文献信息

• Construction of α-Acyloxy Ketones via Photoredox-Catalyzed O–H Insertion of Sulfoxonium Ylides with Carboxylic Acids
  作者：Qing Sun、Yuzhu Peng、Yujing Wang、Xiaoguang Bao

  DOI：10.1021/acs.orglett.3c02221

  日期：2023.9.15

  sulfoxonium ylides with carboxylic acids was advanced under mild and simple conditions, offering a practical approach for preparing α-acyloxy ketones with a broad scope of carboxylic acids. A combined experimental and computational study suggests that this reaction proceeds via a stepwise proton-assisted electron transfer mechanism.

  在此，在温和简单的条件下进行了光氧化还原催化的亚砜叶立德与羧酸的插入，为制备具有广泛羧酸的α-酰氧基酮提供了一种实用的方法。实验和计算相结合的研究表明，该反应通过逐步质子辅助电子转移机制进行。
• Potassium fluoride assisted derivatization of carboxylic acids to phenacyl esters for determination by high-performance liquid chromatography
  作者：Jack M. Miller、Ian D. Brindle、Stephen R. Cater、Kwok-Hung. So、James H. Clark

  DOI：10.1021/ac50064a047

  日期：1980.12.1
• Enantioselective Synthesis of α-Tertiary Hydroxyaldehydes by Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates
  作者：Barry M. Trost、Jiayi Xu、Markus Reichle

  DOI：10.1021/ja067342a

  日期：2007.1.1

  Chiral alpha-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chemistry. Herein, we report the first examples of a catalytic asymmetric protocol for the synthesis of such compounds from readily available alpha-halo or alpha-hydroxy ketones or enol silyl ethers with excellent yields and nantioselectivity. Its synthetic utility is demonstrated in the short, efficient formal synthesis of (S)-oxybutynin. In this process, the chiral ligand controls the regioselectivity as well as the enantioselectivity.
• THORAT, M.;MANE, R.;JAGDALE, M.;SALUNKHE, M., ORG. PREP. AND PROCED. INT., 1986, 18, N 3, 203-205
  作者：THORAT, M.、MANE, R.、JAGDALE, M.、SALUNKHE, M.

  DOI：——

  日期：——