hydroxyproline ethyl ester hydrochloride | 142347-82-8

• 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: hydroxyproline ethyl ester hydrochloride
• 英文别名: cis-4-hydroxy-L-proline ethyl ester; hydrochloride；cis-4-Hydroxy-L-prolin-aethylester; Hydrochlorid；(2S,4S)-2-ethoxycarbonyl-4-hydroxy pyrrolidine hydrochloride；ethyl cis-4-hydroxy-L-prolinate hydrochloride；ethyl (2S,4S)-4-hydroxypyrrolidine-2-carboxylate;hydrochloride
• CAS: 142347-82-8
• 化学式: C₇H₁₃NO₃*ClH
• 分子量: 195.646
• InChiKey: HHXSZDXMSRXWJV-GEMLJDPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.31
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  58.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 储存条件：
  存储在室温下，保持干燥和凉爽。

反应信息

• 作为反应物：
  描述：

  hydroxyproline ethyl ester hydrochloride 在 三乙烯二胺 、 盐酸 、 二异丁基氢化铝 、 碳酸氢钠 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 102.83h， 生成 (1S,2R,6S,7aS)-1,2,6-trihydroxyhexahydro-1H-pyrrolizin-3-one
  参考文献：
  名称：

  An asymmetric substrate-controlled Morita–Baylis–Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines

  摘要：

  We describe herein an approach to the total synthesis of functionalized pyrrolizidinones and pyrrolizidines. The synthetic sequence is based on a highly stereoselective substrate-controlled Morita-Baylis-Hillman (MBH) reaction between a chiral amino-aldehyde and methyl acrylate. The selectivity attained in this reaction was controlled by the presence of a hydroxyl group adequately placed in the structure of the amino-aldehyde used as the nucleophilic component of the MBH reaction. The MBH adducts were used as substrate for an efficient total synthesis of pyrrolizidinones and pyrrolizidines in good overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.050
• 作为产物：
  描述：

  乙醇 、 3-hydroxy-dl-proline 在 盐酸 作用下， 反应 24.0h， 生成 hydroxyproline ethyl ester hydrochloride
  参考文献：
  名称：

  [DE] PROLINDERIVATE ALS PHARMAZEUTISCHE WIRKSTOFFE IN DER TUMORTHERAPIE
  [EN] PROLINE DERIVATIVES USED AS PHARMACEUTICAL ACTIVE INGREDIENTS FOR THE TREATMENT OF TUMOURS
  [FR] DERIVES DE PROLINE COMME PRINCIPES ACTIFS PHARMACEUTIQUES DANS LA THERAPIE DES TUMEURS

  摘要：

  本发明涉及脯氨酸衍生物及其盐，包括这些衍生物的药物，以及使用这些药物治疗肿瘤的方法。此外，本发明还涉及制备上述化合物和药物的方法。

  公开号：

  WO2005058816A1

文献信息

• Synthese d'aminophosphinephosphinites chiraux. Utilisation en reduction asymetrique catalytique
  作者：A. Karim、A. Mortreux、F. Petit、G. Buono、G. Peiffer、C. Siv

  DOI：10.1016/s0022-328x(00)99348-3

  日期：1986.12

  synthesized from natural amino alcohols or by reduction of formyl esters of α-amino acids and PPh2Cl. Their cationic rhodium complexes have been found to be excellent catalysts for enantioselective hydrogenation of dehydroamino acids (ee ∼ 86%, yield ∼ 100%) for example. Asymmetric reduction of ketones can also be performed with the new alkyl AMPP* modified rhodium catalyst (ee 50%).

  由天然氨基醇或通过还原α-氨基酸和PPh 2 Cl的甲酸酯直接合成手性氨基膦次膦酸酯配体（AMPP）。已经发现它们的阳离子铑配合物是脱氢氨基酸的对映选择性加氢的优良催化剂（ee〜86％，收率〜100％）。酮的不对称还原也可以用新型烷基AMPP *改性铑催化剂（ee 50％）进行。
• Benzamide derivatives
  申请人：Teikoku Chemical Industry Co., Ltd.

  公开号：US05143935A1

  公开（公告）日：1992-09-01

  A benzamide derivative represented by the formula: ##STR1## having a promoting activity of gastrointestinal tract and pharmacentical composition containing the same.

  一种由以下公式表示的苯甲酰胺衍生物：##STR1## 具有促进胃肠道活动的作用，以及含有该衍生物的药物组合物。
• OJIMA IWAO; KOGURE TETSUO; YODA NORIKO, J. ORG. CHEM., 1980, 45, NO 23 , 4728-4739
  作者：OJIMA IWAO、 KOGURE TETSUO、 YODA NORIKO

  DOI：——

  日期：——
• US5143935A
  申请人：——

  公开号：US5143935A

  公开（公告）日：1992-09-01
• An asymmetric substrate-controlled Morita–Baylis–Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines
  作者：Kristerson R. Luna-Freire、João Paulo S. Scaramal、Jackson A.L.C. Resende、Cláudio F. Tormena、Fábio L. Oliveira、Ricardo Aparicio、Fernando Coelho

  DOI：10.1016/j.tet.2013.10.050

  日期：2014.5

  We describe herein an approach to the total synthesis of functionalized pyrrolizidinones and pyrrolizidines. The synthetic sequence is based on a highly stereoselective substrate-controlled Morita-Baylis-Hillman (MBH) reaction between a chiral amino-aldehyde and methyl acrylate. The selectivity attained in this reaction was controlled by the presence of a hydroxyl group adequately placed in the structure of the amino-aldehyde used as the nucleophilic component of the MBH reaction. The MBH adducts were used as substrate for an efficient total synthesis of pyrrolizidinones and pyrrolizidines in good overall yield. (C) 2013 Elsevier Ltd. All rights reserved.