ethyl 2-[[(1R)-1-phenylethyl]amino]cyclopentene-1-carboxylate | 163705-83-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl 2-[[(1R)-1-phenylethyl]amino]cyclopentene-1-carboxylate
• CAS: 163705-83-7
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: FRUTXOKKQJIVOB-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-[[(1R)-1-phenylethyl]amino]cyclopentene-1-carboxylate 在 钾硼氢 作用下， 以 甲醇 、 苯 为溶剂， 反应 72.0h， 生成 (S)-1-[2-Carboxy-2-(diethoxy-phosphoryl)-ethyl]-2-hydroxy-cyclopentanecarboxylic acid ethyl ester
  参考文献：
  名称：

  Highly enantioselective synthesis of α-methylene-δ-valerolactones by an asymmetric Michael reaction

  摘要：

  The synthesis of alpha-methylene-6-valerolactones 7, 13, and 19 with enantiomeric excesses of 90-97% was achieved by the asymmetric Michael reaction of chiral imines 3, 9, and 15 with the acrylate 1. Reduction of the carbonyl group of the resulting adducts followed by lactonization and HWE reaction with formaldehyde yielded the lactones as mixtures of diastereoisomers. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.007
• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 、 2-氧代环戊羧酸乙酯 在 三氟化硼乙醚 作用下， 以 苯 为溶剂， 生成 ethyl 2-[[(1R)-1-phenylethyl]amino]cyclopentene-1-carboxylate
  参考文献：
  名称：

  Barta, Nancy S.; Brode, Adam; Stille, John R., Journal of the American Chemical Society, 1994, vol. 116, # 14, p. 6201 - 6206

  摘要：

  DOI：

文献信息

• Diastereo and enantioselective entry to β-amino esters by hydride reduction of homochiral β-enamino esters.
  作者：Cristina Cimarelli、Gianni Palmieri、Giuseppe Bartoli

  DOI：10.1016/0957-4166(94)80111-8

  日期：1994.8

  The reduction of homochiral beta-enamino esters 1 with sodium triacetoxyborohydride, which occurs with good diastereo- and enantioselectivity in the beta-amino esters 2, is described. This procedure allows a straightforward preparation of compounds with known biological activity.
• Stereoselective Reduction of Enantiopure β-Enamino Esters by Hydride:  A Convenient Synthesis of Both Enantiopure β-Amino Esters
  作者：Cristina Cimarelli、Gianni Palmieri

  DOI：10.1021/jo960107y

  日期：1996.1.1

  The reduction of enantiopure beta-enamino esters 1 with sodium triacetoxyborohydride in acetic acid is described. This occurs with good diastereo- and enantioselectivity to yield beta-amino esters 2 and 3 (after hydrogenolysis of the N-chiral group). A model is reported for the origin of the stereoselectivity through an enol ester-diacetoxyborohydride 6, which affords the intramolecular reduction. By choosing the appropriate chiral amine, this procedure allows a straightforward preparation of both the enantiopure beta-amino esters and derivatives with known biological activity, using readily available starting materials and inexpensive reagents and conditions.