(R)-2-(2-吡咯烷基)乙酸甲酯 | 132482-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (R)-2-(2-吡咯烷基)乙酸甲酯
• 英文名称: (2R)-1-tert-butoxycarbonyl-2-carbomethoxymethylpyrrolidine
• 英文别名: tert-butyl (2R)-2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate；tert-butyl (R)-2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate；methyl (R)-2-[N(1')-(tert-butoxycarbonyl)pyrrolidin-2'-yl]ethanoate；(R)-1-tert-butoxycarbonyl-2-carbomethoxymethylpyrrolidine；(R)-2-methoxycarbonylmethyl-pyrrolidine-1-carboxylic acid tert-butyl ester；(R)-1-(tert-Butyloxycarbonyl)pyrrolidin-2-yl-acetic acid methyl ester；(R)-tert-Butyl 2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate
• CAS: 132482-05-4
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: LZYBAKVGAMQFLJ-SECBINFHSA-N

物化性质

• 沸点：
  304.8±15.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-(2-吡咯烷基)乙酸甲酯 在 lithium aluminium tetrahydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 tert-butyl (2R)-2-(2-oxoethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  一种四氢吡啶并[3,4-d]嘧啶衍生物及其在医药上的应用

  摘要：

  本发明涉及一种通式(I)所述的化合物或者其立体异构体、氘代物、溶剂化物、前药、代谢产物、药学上可接受的盐或共晶，及其中间体和制备方法，以及在制备治疗与KRas‑G12C活性或表达量相关疾病的药物中的应用。

  公开号：

  CN112442029A
• 作为产物：
  描述：

  2-(Methoxycarbonylmethylene)pyrrolidine 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 4-二甲氨基吡啶 、 (S,S)-1,3-dimethyl-4,5-(Ph₂PCH₂)2-imidazolidin-2-one 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 生成 (R)-2-(2-吡咯烷基)乙酸甲酯
  参考文献：
  名称：

  Asymmetric synthesis of homoproline derivatives via Rh(I)-catalyzed hydrogenation using chiral bisphosphines as ligands

  摘要：

  It has been demonstrated for the first time that Rh(I)-catalyzed asymmetric hydrogenation of cyclic beta-enamino acid derivatives I using chiral bisphosphines could be a highly efficient synthetic method for optically active homoproline derivatives. The enantioselectivity and conversion yield were largely dependent upon the chiral ligand. Using the Me-BDPMI forming a seven-membered metal chelate, the N-acetylated beta-enamino acid methyl ester la was hydrogenated to give optically active homoproline derivative 2a with 100% conversion and 96% ee. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.014

文献信息

• N-acylpyrrolidin-2-ylalkylbenzamidine derivatives as inhibitors of factor Xa
  申请人：——

  公开号：US20030092698A1

  公开（公告）日：2003-05-15

  This invention is directed to N-acylpyrrolidin-2-ylalkylbenzamidine derivatives which useful for inhibiting the activity of Factor Xa, by contacting said derivatives with a composition containing Factor Xa. The present invention is also directed to compositions containing said derivatives, methods for their preparation, their use, such as in inhibiting the formation of thrombin or for treating a patient suffering from, or subject to, a disease state associated with a physiologically detrimental excess amount of thrombin.

  这项发明涉及N-酰基吡咯啉-2-基烷基苯甲酰胺衍生物，用于通过将这些衍生物与含有凝血因子Xa的组合物接触来抑制凝血因子Xa的活性。本发明还涉及含有这些衍生物的组合物、它们的制备方法，以及它们的用途，例如用于抑制凝血酶的形成或用于治疗患有与生理上有害的凝血酶过量相关的疾病状态的患者。
• [EN] HYDROXAMATE-BASED INHIBITORS OF DEACETYLASES<br/>[FR] COMPOSÉS À BASE D'HYDROXAMATE EN TANT QU'INHIBITEURS DES DÉSACÉTYLASES
  申请人：NOVARTIS AG

  公开号：WO2012025164A1

  公开（公告）日：2012-03-01

  The present teachings relate to compounds of Formula (I): and pharmaceutically acceptable salts, hydrates, esters, and prodrugs thereof, wherein R1, R2, R3, R4, R5, ring A, and Z are as defined herein. The present teachings also provide methods of preparing compounds of Formula (I) and methods of use compounds of Formula (I) in treating pathologic conditions or disorders mediated wholly or in part by deacetylases.

  本教导涉及公式（I）的化合物及其药用盐、水合物、酯和前药，其中R1、R2、R3、R4、R5、环A和Z如本文所定义。本教导还提供制备公式（I）化合物的方法，以及利用公式（I）化合物治疗完全或部分由脱乙酰酶介导的病理状况或疾病的方法。
• Efficient Arndt–Eistert Synthesis of Selective 5-HT₇ Receptor Antagonist SB-269970
  作者：Christina Schjøth-Eskesen、Henrik Helligsø Jensen

  DOI：10.1080/00397910902737155

  日期：2009.8.20

  Abstract This contribution describes a novel Arndt–Eistert approach for the efficient synthesis of the potent and selective 5-HT7-antagonist, (R)-3-(2-(2-(4-methylpiperidin-1-yl)-ethyl)pyrrolidine-1-sulfonyl)phenol (SB-269970), from D-proline. The synthesis was carried out in 10 steps with an overall yield of 23%.

  摘要 该贡献描述了一种新的 Arndt-Eistert 方法，用于有效合成有效且选择性的 5-HT7-拮抗剂，(R)-3-(2-(2-(4-methylpiperidin-1-yl)-ethyl)pyrrolidine -1-磺酰基）苯酚 (SB-269970)，来自 D-脯氨酸。合成分10步进行，总产率为23%。
• Hydroxamate-Based Inhibitors of Deacetylases
  申请人：BROOKS Clinton A.

  公开号：US20110060009A1

  公开（公告）日：2011-03-10

  The present teachings relate to compounds of Formula I: and pharmaceutically acceptable salts, hydrates, esters, and prodrugs thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , ring A, and Z are as defined herein. The present teachings also provide methods of preparing compounds of Formula I and methods of use compounds of Formula I in treating pathologic conditions or disorders mediated wholly or in part by deacetylases.

  本教导涉及Formula I的化合物：及其药用盐、水合物、酯和前药，其中R1、R2、R3、R4、R5、环A和Z的定义如本文所述。本教导还提供制备Formula I化合物的方法，以及利用Formula I化合物治疗完全或部分由去乙酰酶介导的病理状况或疾病的方法。
• Investigation of the 4-O-alkylamine substituent of non-peptide quinolone GnRH receptor antagonists
  作者：Robert J. DeVita、Mark T. Goulet、Matthew J. Wyvratt、Michael H. Fisher、Jane-L. Lo、Yi Tien Yang、Kang Cheng、Roy G. Smith

  DOI：10.1016/s0960-894x(99)00447-3

  日期：1999.9

  appropriate cyclic D- or L-amino acids by the Amdt-Eistert homologation followed by reduction of the resulting esters. Incorporation of these pharmacophores was achieved via a novel Mitsunobu alkylation of 4-hydroxyquinolones. The key amine pharmacophore for binding to the rat GnRH receptor was most active in the S-configuration. Ring size was not important for potency with 4, 5, 6, and 7-membered ring amines

  报道了喹诺酮GnRH拮抗剂（+/-）-1对映体的合成和体外活性。由适当的环状D-或L-氨基酸，通过Amdt-Eistert同系反应，然后还原所得酯，制备手性氨基醇。这些药效基团的掺入是通过4-羟基喹诺酮类的新Mitsunobu烷基化实现的。与大鼠GnRH受体结合的关键胺药效团在S构型中最活跃。环的大小对于效能而言并不重要，其中4、5、6和7元环胺表现出相似的效能。