2-(R)-乙氧羰基-4-(R)-羟基吡咯烷 | 61478-25-9

• 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
• 中文名称: 2-(R)-乙氧羰基-4-(R)-羟基吡咯烷
• 英文名称: cis-4-hydroxy-DL-prolin-ethyl ester
• 英文别名: cis-4-Hydroxy-DL-prolin-aethylester；(2R,4R)-ethyl 4-hydroxypyrrolidine-2-carboxylate；ethyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate
• CAS: 61478-25-9；80174-38-5；80174-40-9；132666-67-2
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: JMHQESARJMGVCZ-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 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：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(R)-乙氧羰基-4-(R)-羟基吡咯烷 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 ethyl (8R)-7-benzyl-2,4-dioxo-1,3,7-triazaspiro[4.4]nonane-8-carboxylate
  参考文献：
  名称：

  Design and synthesis of APTCs (aminopyrrolidinetricarboxylic acids): Identification of a new group III metabotropic glutamate receptor selective agonist

  摘要：

  A new family of mGlu receptor orthosteric ligands called APTCs was designed and synthesized using a parallel chemistry approach. Amongst 65 molecules tested on mGlu4, mGlu6 and mGlu8 subtypes, (2S,4S)-4-amino-1-[(E)-3-carboxyacryloyl]pyrrolidine-2,4-dicarboxylic acid (8a06-FP0429) has been shown to be a full mGlu4 agonist and a partial mGlu8 agonist. In addition, 8a06 was shown to be selective versus group I and II mGlu subtypes. A possible explanation for this efficacy difference is proposed by docking experiment performed with molecular model of the receptor. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.062
• 作为产物：
  描述：

  (2R,4R)-ethyl N¹-benzyl-4-hydroxypyrrolidine-2-carboxylate 在 氢气 、 palladium(II) hydroxide 作用下， 反应 3.0h， 生成 2-(R)-乙氧羰基-4-(R)-羟基吡咯烷
  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

• Synthesis of (1<i>R</i>,4<i>R</i>)- and (1<i>S</i>,4<i>S</i>)-2,5-Diazabicyclo[2.2.1]heptanes and Their<i>N</i>-Substituted Derivatives
  作者：Ulrich Jordis、Fritz Sauter、Suhaib M. Siddiqi、Bernhard Küenburg、Kaberi Bhattacharya

  DOI：10.1055/s-1990-27056

  日期：——

  Derivatives of the (1R,4R)- and (1S,4S)-2,5-diazabicyclo- [2.2.1]heptane ring system are prepared in enantiomerically pure form from trans-4-hydroxy-L-proline (2). The target compounds are precursors of antibacterial quinolone carboxyclic acids.

  (1R,4R)-和(1S,4S)-2,5-二氮杂双环[2.2.1]庚烷环系的衍生物以对映体纯形式从反式-4-羟基-L-脯氨酸（2）中制备而成。目标化合物是抗菌喹啉羧酸的前体。
• Design and stereoselective synthesis of four peptide nucleic acid monomers with cyclic structures in backbone
  作者：Akiko Watanabe、Naotoshi Kiyota、Tetsuo Yamasaki、Kazuhiro Tanda、Tatsunori Miyagoe、Masanori Sakamoto、Masami Otsuka

  DOI：10.1002/jhet.627

  日期：2011.9

  isomers of the monomer of peptide nucleic acid (PNA) were derived from (2S,4R)‐4‐hydroxyproline; they had different stereochemistries at the C2 and C4 positions in the pyrrolidine ring. These different backbone conformations corresponding to four different stereochemistries were realized through a combination of inversions at the C2 and the C4 positions in pyrrolidine ring. The obtained backbone frameworks

  肽核酸（PNA）单体的四个异构体衍生自（2 S，4 R）-4-羟基脯氨酸; 它们在吡咯烷环的C 2和C 4位置具有不同的立体化学。通过组合在吡咯烷环中C 2和C 4位置上的转化，实现了与四个不同立体化学相对应的这些不同的主链构象。将获得的主链骨架与N-苯甲酰基胸腺嘧啶反应，得到相应的PNA单体。所得单体的光谱比较证实了其​​立体化学。J.杂环化​​学。（2011）。
• [EN] INHIBITORS OF THE BCL6 BTB DOMAIN PROTEIN-PROTEIN INTERACTION AND USES THEREOF<br/>[FR] INHIBITEURS DE L'INTERACTION PROTÉINE-PROTÉINE DU DOMAINE BCL6 BTB ET LEURS UTILISATIONS
  申请人：ONTARIO INSTITUTE FOR CANCER RES OICR

  公开号：WO2019153080A1

  公开（公告）日：2019-08-15

  The present application relates to compounds of Formula I (I) or pharmaceutically acceptable salts, solvates and/or prodrugs thereof, to compositions comprising these compounds or pharmaceutically acceptable salts, solvates and/or prodrugs thereof, and various uses in the treatment of diseases, disorders or conditions that are treatable by inhibiting interactions with BCL6 BTB, such as cancer.

  本申请涉及公式I（I）化合物或其药用可接受的盐、溶剂化合物和/或前药，包括含有这些化合物或药用可接受的盐、溶剂化合物和/或前药的组合物，以及在治疗可通过抑制与BCL6 BTB的相互作用可治疗的疾病、紊乱或状况中的各种用途，如癌症。
• Efficient Asymmetric Hydrogenation of .ALPHA.-Amino Ketone Derivatives. A Highly Enantioselective Synthesis of Phenylephrine, Levamisole, Carnitine and Propranolol.
  作者：Shunji SAKURABA、Hisashi TAKAHASHI、Hideo TAKEDA、Kazuo ACHIWA

  DOI：10.1248/cpb.43.738

  日期：——

  The complexes of pyrrolidine bisphosphine ligands (CPMs) with rhodium (I) were found to be efficient catalysts for asymmetric hydrogenation of α-amino ketone hydrochloride derivatives. Utilizing this methodology, we have developed efficient asymmetric syntheses of the optically active β-amino alcohols, phenylephrine, levamisole, carnitine and propranolol.

  吡咯烷双膦配体（CPMs）与铑（I）形成的复合物被发现是α-氨基酮 hydrochloride 衍生物的不对称加氢反应的高效催化剂。利用这一方法，我们开发了光学活性的β-氨基醇、苯肾上腺素、左旋咪唑、肉碱和普萘洛尔的高效不对称合成。
• [EN] ANDROGEN RECEPTOR MODULATOR COMPOUNDS AND METHODS<br/>[FR] COMPOSES MODULATEURS DE RECEPTEUR D'ANDROGENES ET PROCEDES
  申请人：LIGAND PHARM INC

  公开号：WO2005090282A1

  公开（公告）日：2005-09-29

  Provided herein are compounds having a structure selected from among Formula (I), Formula (II), Formula (III), Formula (IV), Formula (V) and Formula (VI) that are androgen receptor modulators and/or androgen receptor binding agents. Also disclosed are methods of making and using such compounds, including, but not limited to, using such compounds for treating various conditions.

  本文提供了具有以下结构的化合物，这些结构选自公式(I)、公式(II)、公式(III)、公式(IV)、公式(V)和公式(VI)，这些化合物是雄激素受体调节剂和/或雄激素受体结合剂。还公开了制备和使用这些化合物的方法，包括但不限于将这些化合物用于治疗各种疾病的方法。