ethyl (2S,4S)-1-benzyl-4-hydroxyprolinate | 627100-73-6

• 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: ethyl (2S,4S)-1-benzyl-4-hydroxyprolinate
• 英文别名: ethyl (2S,4S)-1-benzyl-4-hydroxypyrrolidine-2-carboxylate
• CAS: 627100-73-6
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: MZCRIMVOOXQIAJ-STQMWFEESA-N

物化性质

• 沸点：
  364.2±42.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2S,4S)-1-benzyl-4-hydroxyprolinate 在 吡啶 作用下， 以 二甲基亚砜 为溶剂， 反应 52.0h， 生成 ethyl (2S,4R)-1-benzyl-4-cyanoprolinate
  参考文献：
  名称：

  Ex-chiral pool synthesis and receptor binding studies of 4-substituted prolinol derivatives

  摘要：

  Starting from natural 4-hydroxyproline, preparation of the four possible stereoisomers of 4-amino- and 4-aminomethyl-substituted prolinol derivatives, respectively, was accomplished by chemo- and regioselective functional group transformations at the 2- and 4-positions of the pyrrolidine moiety. These building blocks were used as valuable precursors for the preparation of new methoxybenzamide derivatives. Dopamine and serotonin binding studies involving the subtypes D1, D2(long), D2(short), D3 and D4 as well as 5-HT1(A) and 5-HT2 respectively, displayed interesting structure activity relationships, especially with respect to the absolute and relative configuration of the test compounds. As a complement to the D3 receptor preferring aminomethylpyrrolidine FAUC 21. the (2R,4R)-aminoprolinol derivative ent-24 (FAUC 65) preferentially recognizing the D4 subtype was developed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.019
• 作为产物：
  描述：

  N-苄基甘氨酸乙酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 31.08h， 生成 ethyl (2S,4S)-1-benzyl-4-hydroxyprolinate
  参考文献：
  名称：

  A short diastereoselective synthesis of cis-(2S,4S) and cis-(2R,4R)-4-hydroxyprolines

  摘要：

  A concise synthesis of (2R,4R)-4-hydroxyproline (1) and (2,5,45)-4-hydroxyproline (2) has been developed in enantiomerically pure form from commercially available starting materials with excellent diastereoselectivity. The tightly bound chelation controlled transition state formed during the 5-exo-tet ring closure reaction is assumed to be the origin of high diastereoselectivity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.03.119

文献信息

• Enantiospecific synthesis and receptor binding of novel dopamine receptor ligands employing natural 4-hydroxyproline as a practical and flexible building block
  作者：Cornelia Heindl、Harald Hübner、Peter Gmeiner

  DOI：10.1016/j.tetasy.2003.08.020

  日期：2003.10

  Starting from natural 4-hydroxyproline, an ex-chiral pool approach is described giving access to 2-aminoalkylpyrrolidine derivatives that were used as chiral building blocks for the synthesis of bioactive 2-methoxybenzamide derivatives. The 4-hydroxy substituent can be displaced employing organocuprates as useful carbanion equivalents. Dopamine and serotonin binding studies involving the subtypes D1

  从天然的4-羟基脯氨酸开始，描述了一种手性前池方法，该方法可得到2-氨基烷基吡咯烷衍生物，该衍生物用作合成生物活性2-甲氧基苯甲酰胺衍生物的手性构件。可以使用有机铜酸盐作为有用的碳负当量置换4-羟基取代基。多巴胺和涉及亚型D1，D2血清素结合研究长，D2短，D3和D4，以及5-HT1甲和5-HT2，分别提供有趣的见解立体结构活性关系。（2 S，4 R）-2-氨基甲基吡咯烷衍生物ent -66和（2 R，4 S）-2-氨基乙基吡咯烷衍生物68分别显示出对多巴胺D3和D4受体亚型的显着亲和力和偏爱性，两者都被认为与精神分裂症的症状有关。