(R)-(-)-2-phenylmethyl glycidyl ether | 151715-99-0

• 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: (R)-(-)-2-phenylmethyl glycidyl ether
• 英文别名: (R)-(-)-2-phenylethyl glycidyl ether；(2R)-2-(2-phenylethoxymethyl)oxirane
• CAS: 151715-99-0
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: LMTJPHNFBSNLHM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 (R)-(-)-2-phenylmethyl glycidyl ether 在 sodium 作用下， 反应 3.0h， 生成 (R)-1-phenylethyl-3-methoxy-1,2-propanediol
  参考文献：
  名称：

  Enzymatic resolution of butanoic esters of 1-phenyl, 1-phenylmethyl, 1-[2-phenylethyl] and 1-12-phenoxyethyl] ethers of 3-methoxy-1,2-propanediol

  摘要：

  The enzymatic hydrolysis of butanoic esters of 1-phenyl-, 1-phenylmethyl-, 1-[2-phenylethyl] and 1-[2-phenoxyethyl] ethers of 3-methoxy-1,2-propanediol has been studied by using lipases. Highest enantioselectivity E was obtained with Amano PS lipase for the phenyl ether E almost-equal-to 55, and with lipase B from Candida antarctica for the other derivatives, E almost-equal-to 20, >100 and >55 respectively. The absolute configurations of the products were verified from comparison with reference compounds synthesised from (S)-epichlorohydrin or (S)-glycidol.

  DOI：

  10.1016/s0957-4166(00)80077-4
• 作为产物：
  描述：

  1-<2-phenylethyl>-3-chloro-1,2-propanediol 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 phosphate buffer 作用下， 以 甲醇 为溶剂， 反应 9.7h， 生成 (R)-(-)-2-phenylmethyl glycidyl ether
  参考文献：
  名称：

  Enzymatic resolution of butanoic esters of 1-phenylmethyl and 1-[2-phenylethyl] ethers of 3-chloro-1,2-propanediol

  摘要：

  The enzymatic hydrolysis of butanoic esters of 1-phenylmethyl- and 1-[2-phenylethyl] ethers of 3-chloro-1,2-propanediol has been studied by using lipases. Highest enantiomeric ratio was obtained with PPL for the phenylmethyl ether and with Amano SAM II for the phenylethyl ether. The absolute configurations of the products were verified in two ways. Both the produced alcohols and the remaining esters were converted into the corresponding glycidyl ethers which also were synthesised in homochiral forms starting from (S)- epichlorohydrin. The produced alcohols and the remaining esters were prepared independently from (S)-epichlorohydrin.

  DOI：

  10.1016/s0957-4166(00)80140-8

文献信息

• Enzymatic resolution of butanoic esters of 1-phenylmethyl and 1-[2-phenylethyl] ethers of 3-chloro-1,2-propanediol
  作者：Vassilia Partali、Viggo Waagen、Thor Alvik、Thorleif Anthonsen

  DOI：10.1016/s0957-4166(00)80140-8

  日期：1993.5

  The enzymatic hydrolysis of butanoic esters of 1-phenylmethyl- and 1-[2-phenylethyl] ethers of 3-chloro-1,2-propanediol has been studied by using lipases. Highest enantiomeric ratio was obtained with PPL for the phenylmethyl ether and with Amano SAM II for the phenylethyl ether. The absolute configurations of the products were verified in two ways. Both the produced alcohols and the remaining esters were converted into the corresponding glycidyl ethers which also were synthesised in homochiral forms starting from (S)- epichlorohydrin. The produced alcohols and the remaining esters were prepared independently from (S)-epichlorohydrin.
• Enzymatic resolution of butanoic esters of 1-phenyl, 1-phenylmethyl, 1-[2-phenylethyl] and 1-12-phenoxyethyl] ethers of 3-methoxy-1,2-propanediol
  作者：Viggo Waagen、Ingjerd Hollingsaeter、Vassilia Partali、Olav Thorstad、Thorleif Anthonsen

  DOI：10.1016/s0957-4166(00)80077-4

  日期：1993.10

  The enzymatic hydrolysis of butanoic esters of 1-phenyl-, 1-phenylmethyl-, 1-[2-phenylethyl] and 1-[2-phenoxyethyl] ethers of 3-methoxy-1,2-propanediol has been studied by using lipases. Highest enantioselectivity E was obtained with Amano PS lipase for the phenyl ether E almost-equal-to 55, and with lipase B from Candida antarctica for the other derivatives, E almost-equal-to 20, >100 and >55 respectively. The absolute configurations of the products were verified from comparison with reference compounds synthesised from (S)-epichlorohydrin or (S)-glycidol.