methyl 2-acetoxy 3-phenyl propanoate | 134540-58-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2-acetoxy 3-phenyl propanoate
• 英文别名: methyl 2-acetoxy-3-phenylpropionate；2-acetoxy-3-phenyl-propionic acid methyl ester；2-Acetoxy-3-phenyl-propionsaeure-methylester；Methyl 2-acetyloxy-3-phenylpropanoate
• CAS: 134540-58-2
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: NXQMRHPIOJUVFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙醛 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 水 、 对甲苯磺酸 、 sodium hydrogensulfite 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 methyl 2-acetoxy 3-phenyl propanoate
  参考文献：
  名称：

  脂肪酶PS-30催化的立体选择性酰化反应对扁桃酸酯的动力学拆分

  摘要：

  通过使用脂肪酶PS-30作为催化剂，已通过立体选择性酰化反应实现了一系列外消旋扁桃酸酯的动力学拆分。动力学对映体比率（E）的值达到197.5。简要讨论了取代基的作用。

  DOI：

  10.1016/j.tetlet.2014.02.095

文献信息

• Synthesis of α-diazoesters from α-hydrazonoesters: Utilization of α-hydrazonoesters and α-diazoesters for convenient interconversion
  作者：Eiko Yasui、Kanako Ishimine、Sohta Nitanai、Nanami Hatakeyama、Shinji Nagumo

  DOI：10.1016/j.tetlet.2022.153730

  日期：2022.4

  We have developed a novel method to synthesize α-diazoesters from α-hydrazonoesters with a catalytic amount of Cu(OAc)2 in acetonitrile. When the reaction was carried out under an argon atmosphere, the reaction stopped halfway, suggesting that this reaction required oxygen to reoxidize the catalyst. Since hydrazonoesters can be obtained by reduction of α-diazoesters with P(n-Bu)3 in diisopropyl ether

  我们开发了一种在乙腈中催化量的 Cu(OAc) 2由 α-肼酯合成 α-重氮酯的新方法。当反应在氩气氛下进行时，反应中途停止，表明该反应需要氧气来重新氧化催化剂。由于可以通过在二异丙醚中用 P( n - Bu) 3还原 α-重氮酯来获得肼酯，因此这两种化合物很容易相互转化。α-重氮酯不稳定且不适合储存，而肼酯更稳定，尤其是结晶肼酯。因此，适合长期储存的腙酸酯可以方便地用作α-重氮酯的前体。
• Conversion of Esters to 2-Acetoxy Esters via 2-Nosyloxy Esters
  作者：Robert V. Hoffman、Deborah Stoll

  DOI：10.1080/00397919108020815

  日期：1991.1

  Reaction of 2-nosyloxy esters, available in high yields from the reaction of trimethylsilyl ketene acetals with p-((nitrobenzene)sulfonyl) peroxide, with sodium acetate in DMF produces 2-acetoxy ester in good yields.
• Oxidation of α-Acetoxy Acetals with Trichloroisocyanuric Acid
  作者：Marta Benincasa、Romano Grandi、Franco Ghelfi、Ugo M. Pagnoni

  DOI：10.1080/00397919508013870

  日期：1995.11

  alpha-Acetoxy acid methyl esters are prepared in excellent yields by treating aliphatic alpha-acetoxy dimethyl acetals with trichloroisocyanuric acid in DMF.
• Selective transformations of threo-2,3-dihydroxy esters
  作者：Paul R. Fleming、K. Barry Sharpless

  DOI：10.1021/jo00008a051

  日期：1991.4

  Two highly regio- and stereoselective transformation of threo-2,3-dihydroxy esters have been developed. In the first reaction, the alpha-hydroxy group is converted into a sulfonate group (tosylate or nosylate); the alpha-tosylates and alpha-nosylates are then subjected to basic conditions (K2CO3/ROH) to give erythro glycidic esters in high yield. The alpha-nosylates are also suitable electrophiles for azides, giving access to erythro-alpha-azido-beta-hydroxy esters. The second reaction involves conversion of the diol esters to acetoxy bromo esters. The beta-substituent plays a key role in determining the regiochemistry since cases with beta-alkyl substituents afford beta-acetoxy-alpha-bromo esters exclusively, whereas a beta-phenyl substituent directs formation of the alpha-acetoxy-beta-bromo ester. The acetoxy bromo esters can subsequently be converted to the threo glycidic esters (via the bromohydrin esters); selective hydrogenolysis of the bromine substituent can also be achieved.
• CCCLXXXVII.—The relationship between the optical rotatory powers and the relative configurations of optically active compounds. Part II. The relative configurations of the optically active mandelic acids and β-phenyl-lactic acids
  作者：George William Clough

  DOI：10.1039/ct9252702808

  日期：——