N-(2-acetoxy-2-phenyl)ethylphthalimide | 102028-68-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(2-acetoxy-2-phenyl)ethylphthalimide
• 英文别名: acetic acid-(1-phenyl-2-phthalimido-ethyl ester)；Essigsaeure-(1-phenyl-2-phthalimido-aethylester)
• CAS: 102028-68-2
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: OJWUISOJMDIXIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(2-acetoxy-2-phenyl)ethylphthalimide 在 Arthrobacter sp. MTCC 5125 作用下， 反应 24.0h， 生成 (S)-2-phthalimido-1-phenyl-ethanol
  参考文献：
  名称：

  Arthrobacter sp. lipase immobilization for preparation of enantiopure masked β-amino alcohols

  摘要：

  Recent reports on immobilization of lipase from Arthrobacter sp. (ABL, MTCC 5125; IIIM isolate) on insoluble polymers have shown altered properties including stability and enantioselectivity. Present work demonstrates a facile method for the preparation of enantiopure beta-amino alcohols by modulation of ABL enzyme properties via immobilization on insoluble as well as soluble supports using entrapment/covalent binding techniques. Efficacies of immobilized ABL on insoluble supports prepared from tetraethylorthosilicate/aminopropyltriethoxy silane and soluble supports derived from copolymerization of N-vinyl pyrrolidone-allylglycidyl ether (ANP type)/N-vinyl pyrrolidone-glycidyl methacrylate ( GNP type) for kinetic resolution of masked beta-amino alcohols have been studied vis-a-vis free ABL enzyme/wet cell biomass. The immobilized lipase on different insoluble/soluble supports has shown 21 - 110 mg/g protein binding and 30 - 700 U/g activity for hydrolyzing tributyrin substrate. The findings have shown a significant enhancement in enantioselectivity (ee 99%) vis-a-vis wet cell biomass providing ee 70-90% for resolution of beta-amino alcohols. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.023
• 作为产物：
  描述：

  氧化苯乙烯 在 sodium hydroxide 、 水 、 sodium acetate 作用下， 生成 N-(2-acetoxy-2-phenyl)ethylphthalimide
  参考文献：
  名称：

  Terada, Nippon Kagaku Zasshi, 1956, vol. 77, p. 1265

  摘要：

  DOI：

文献信息

• An expedient chemo-enzymatic method for the synthesis of optically active masked 1,2-amino alcohols
  作者：Pankaj Gupta、Subhash C. Taneja、Bhahwal A. Shah、Debaraj Mukherjee、Rajinder Parshad、Swapandeep S. Chimni、Ghulam N. Qazi

  DOI：10.1016/j.tetasy.2008.08.004

  日期：2008.8

  of enantiopure masked 1,2-amino alcohols (ee >99%) including their alkyl substituted analogues has been achieved by the regioselective ring opening of epoxides using phthalimide, followed by highly efficient kinetic resolution under mild and environmentally friendly conditions. The addition of co-solvents during kinetic resolution significantly improved the enantioselectivity with reduction in time

  通过使用邻苯二甲酰亚胺在环氧化物上进行区域选择性开环，然后在温和且环境友好的条件下进行高效动力学拆分，可以实现对映体纯的掩蔽的1,2-氨基醇（ee> 99％）（包括烷基取代的类似物）的简便合成。在动力学拆分过程中添加助溶剂可显着提高对映选择性，并减少时间。