(2R,3R)-(+)-ethyl 3-cyclohexy-2,3-epoxypropionate | 132486-45-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2R,3R)-(+)-ethyl 3-cyclohexy-2,3-epoxypropionate
• 英文别名: ethyl (2R,3R)-3-cyclohexyloxirane-2-carboxylate
• CAS: 132486-45-4
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: AWUWTBXBMDBZHG-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,3R)-(-)-ethyl 3-cyclohexyl-2,3-dihydroxypropionate 在 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 93.0h， 生成 (2R,3R)-(+)-ethyl 3-cyclohexy-2,3-epoxypropionate
  参考文献：
  名称：

  Selective transformations of threo-2,3-dihydroxy esters

  摘要：

  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.

  DOI：

  10.1021/jo00008a051

文献信息

• The Synthesis of Solvent-Free Glycidic Esters from Diazoesters and Carbonyl Compounds Catalysed by Lanthanide Triflates
  作者：Massimo Curini、Francesco Epifano、Maria Carla Marcotullio、Ornelio Rosati

  DOI：10.1002/1099-0690(200205)2002:9<1562::aid-ejoc1562>3.0.co;2-q

  日期：2002.5

  and carbonyl compounds catalysed by lanthanide triflates are described. Aldehydes, and α-unsubstituted and α-monosubstituted cyclohexanones react to give the selective formation of α,β-epoxy esters (glycidic esters), whereas other ketones are unreactive. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  描述了重氮化镧三氟甲磺酸酯催化的重氮乙酸乙酯与羰基化合物之间反应的结果。醛与α-未取代和α-单取代的环己酮反应生成α，β-环氧酯（缩水甘油酯）的选择性形成，而其他酮则没有反应性。（©Wiley-VCH Verlag GmbH，69451 Weinheim，Germany，2002）
• FLEMING, PAUL R.;SHARPLESS, K. BARRY, J. ORG. CHEM., 56,(1991) N, C. 2869-2875
  作者：FLEMING, PAUL R.、SHARPLESS, K. BARRY

  DOI：——

  日期：——