3-oxo-3-[1-(1'(S)-α-methylbenzyl)-aziridin-2(R)-yl]-propionic acid tert-butyl ester | 312728-09-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 3-oxo-3-[1-(1'(S)-α-methylbenzyl)-aziridin-2(R)-yl]-propionic acid tert-butyl ester
• 英文别名: tert-butyl 3-oxo-3-[(2R)-1-[(1S)-1-phenylethyl]aziridin-2-yl]propanoate
• CAS: 312728-09-9
• 化学式: C₁₇H₂₃NO₃
• 分子量: 289.375
• InChiKey: UJDGRGDIKMASOI-CKZVMRIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-oxo-3-[1-(1'(S)-α-methylbenzyl)-aziridin-2(R)-yl]-propionic acid tert-butyl ester 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 TEA 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 18.0h， 生成 3(S)-(tert-butyldimethylsilanyloxy)-3-[1-(1'(S)-α-methylbenzyl)-aziridin-2(R)-yl]-propionic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of protected threo-β-hydroxy-l-glutamic acid using a chiral aziridine

  摘要：

  Threo-beta-hydroxy-L-glutamic acid derivatives with different carboxylic acid protecting groups were stereoselectively prepared from a chiral aziridine-2-carboxylate using an aldol reaction, stereoselective ketone reduction, and aziridine ring transformation. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00311-6
• 作为产物：
  描述：

  醋酸叔丁酯 、 ethyl 1-[(S)-1-phenylethyl]aziridine-(R)-carboxylate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以88%的产率得到3-oxo-3-[1-(1'(S)-α-methylbenzyl)-aziridin-2(R)-yl]-propionic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of protected threo-β-hydroxy-l-glutamic acid using a chiral aziridine

  摘要：

  Threo-beta-hydroxy-L-glutamic acid derivatives with different carboxylic acid protecting groups were stereoselectively prepared from a chiral aziridine-2-carboxylate using an aldol reaction, stereoselective ketone reduction, and aziridine ring transformation. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00311-6

文献信息

• Stereoselective synthesis of protected threo-β-hydroxy-l-glutamic acid using a chiral aziridine
  作者：Chan Sun Park、Hawn Geun Choi、Hyunjoo Lee、Won Koo Lee、Hyun-Joon Ha*

  DOI：10.1016/s0957-4166(00)00311-6

  日期：2000.8

  Threo-beta-hydroxy-L-glutamic acid derivatives with different carboxylic acid protecting groups were stereoselectively prepared from a chiral aziridine-2-carboxylate using an aldol reaction, stereoselective ketone reduction, and aziridine ring transformation. (C) 2000 Published by Elsevier Science Ltd.