(1S,2R,αR)-2--1-(carbobenzyloxy)cyclopentane | 163705-84-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2R,αR)-2--1-(carbobenzyloxy)cyclopentane
• 英文别名: benzyl (1S,2R)-2-[[(1R)-1-phenylethyl]amino]cyclopentane-1-carboxylate
• CAS: 163705-84-8
• 化学式: C₂₁H₂₅NO₂
• 分子量: 323.435
• InChiKey: NACDUSBHYWRDJS-LSTHTHJFSA-N

物化性质

• 沸点：
  441.7±40.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (1S,2R,αR)-2--1-(carbobenzyloxy)cyclopentane 在 palladium dihydroxide 氢气 作用下， 生成 (1S,2R)-2-氨基环戊烷甲酸
  参考文献：
  名称：

  Diastereo and enantioselective entry to β-amino esters by hydride reduction of homochiral β-enamino esters.

  摘要：

  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.

  DOI：

  10.1016/0957-4166(94)80111-8
• 作为产物：
  描述：

  2--amino-1-carbobenzoxycyclopentene 在 三乙酰氧基硼氢化钠 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 4.0h， 以71%的产率得到(1S,2R,αR)-2--1-(carbobenzyloxy)cyclopentane
  参考文献：
  名称：

  Stereoselective Reduction of Enantiopure β-Enamino Esters by Hydride:  A Convenient Synthesis of Both Enantiopure β-Amino Esters

  摘要：

  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.

  DOI：

  10.1021/jo960107y

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.
• AN IMPROVED SYNTHESIS OF ENANTIOPURE β-AMINO ACIDS
  作者：Cristina Cimarelli、Gianni Palmieri、Emanuela Volpini

  DOI：10.1081/scc-100105666

  日期：2001.1

  An improved method for the preparation of both the enantiopure beta -amino acids is presented. The diastereomer benzyl beta -amino esters, obtained by stereoselective reduction of beta -enamino esters, were separated and hydrogenolyzed to the free enantiopure beta -amino acids.