carbonic acid methyl ester 2-oxo-2-phenyl-ethyl ester | 252979-70-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: carbonic acid methyl ester 2-oxo-2-phenyl-ethyl ester
• 英文别名: phenacyl methyl carbonate；carbonic acid methyl ester-phenacyl ester；Kohlensaeure-methylester-phenacylester；Methyl phenacyl carbonate
• CAS: 252979-70-7
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: YYBCWZIMWQJLEB-UHFFFAOYSA-N

物化性质

• 沸点：
  290.3±23.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  carbonic acid methyl ester 2-oxo-2-phenyl-ethyl ester 在 9,10-二甲基蒽 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以83%的产率得到甲醇
  参考文献：
  名称：

  Photoreleasable protecting groups on alcohols, phosphates and diacids and the use thereof

  摘要：

  酒精、磷酸酯和二酸衍生物可能通过辐射去保护，所使用的保护基是芳基酰基或杂环芳基酰基。

  公开号：

  US06392089B1
• 作为产物：
  描述：

  碳酸,甲基1-苯基-2-丙烯基酯 在 臭氧 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到carbonic acid methyl ester 2-oxo-2-phenyl-ethyl ester
  参考文献：
  名称：

  DABCO-catalyzed formation of 4-methoxy-1,3-dioxolan-2-ones and their synthetic applications in the aromatic electrophilic substitution

  摘要：

  DABCO is a very effective catalyst in the formation of 4-methoxy-1,3-dioxolan-2-ones 10 from the corresponding alpha-carbonatoaldehydes 8 intermediates. The Friedel-Crafts reaction pathway of the cyclic carbonate 10 is dependent on the electron density of the aromatic nucleophiles. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.173

文献信息

• A Direct Catalytic and Diastereoselective Aldol Route to Protected α,β-Dihydroxyketones
  作者：Michael C. Willis、Gary A. Cutting、Matthew P. John

  DOI：10.1055/s-2004-822921

  日期：——

  The combination of Mg(ClO4)2, bipyridine (bipy) and N-methyl morpholine generates an effective catalyst for the direct addition of α-carbonate substituted ketones to aromatic aldehydes. The diol containing products undergo direct cyclic carbonate ­formation to provide protected adducts in good yield with high syn-aldol diastereoselectivity.

  将 Mg（ClO4）2、联吡啶（bipy）和 N-甲基吗啉结合在一起可生成一种有效的催化剂，用于将δ-碳酸酯取代的酮直接加成到芳香醛中。含有二元醇的产物会直接形成环状碳酸酯，从而以良好的收率和较高的合成-醛非对映选择性提供受保护的加合物。
• Photoreleasable protecting groups based on electron transfer chemistry. Donor sensitized release of phenacyl groups from alcohols, phosphates and diacids
  作者：Anamitro Banerjee、Kwangjoo Lee、Daniel E. Falvey

  DOI：10.1016/s0040-4020(99)00754-1

  日期：1999.10

  The electron transfer mediated photochemical release of alcohols, phosphates and diacids is examined. The alcohols can be protected as mixed phenacyl carbonate esters. Irradiation of mixtures containing electron donating sensitizers and phenacyl alkyl carbonate ester initiates a series of bond scission reactions that result in clean release of the corresponding alcohols. This was demonstrated for a variety of primary, secondary and tertiary hydroxyl groups, including the 5'-hydroxy group of thymidine. Sensitizers that were effective in promoting photolytic release include 9,10-dimethylanthracene and 9-methylcarbazole. GC/MS and NMR analysis of the by-products formed in these release reactions implicates the intermediacy of radical ion intermediates in these reactions. It is further demonstrated that the electron transfer sensitized release method can be extended to phosphate esters and di-functional acids. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.
• Fischer,E.; Fischer,H.O.L., Chemische Berichte, 1914, vol. 47, p. 775
  作者：Fischer,E.、Fischer,H.O.L.

  DOI：——

  日期：——
• Direct catalytic diastereoselective Mannich reactions: the synthesis of protected α-hydroxy-β-aminoketones
  作者：Nikki E. Stainforth、Gary A. Cutting、Matthew P. John、Michael C. Willis

  DOI：10.1016/j.tetasy.2009.03.026

  日期：2009.5

  The combination of Mg(ClO4)(2), 2,2'-bipyridine and N-methylmorpholine generates an effective catalyst system for the direct addition of alpha-carbonate-substituted ketones to aryl N-Ts imines. Methyl-carbonate-substituted ketones deliver acyclic alpha-hydroxy-beta-aminoketone derivates, while ketones Substituted with alpha-iso-propenyl-carbonates furnish cyclic carbamate adducts. In both cases the anti-configured Mannich products dominate. (C) 2009 Elsevier Ltd. All rights reserved.