Ethyl 3-pyrrolidinobutyrate | 42980-67-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl 3-pyrrolidinobutyrate
• 英文别名: 3-pyrrolidin-1-yl-butanoic acid ethyl ester；Ethyl 3-(1-pyrrolidinyl)butanoate；ethyl 3-pyrrolidin-1-ylbutanoate
• CAS: 42980-67-6
• 化学式: C₁₀H₁₉NO₂
• 分子量: 185.266
• InChiKey: XOHFSJRAEGVBNY-UHFFFAOYSA-N

物化性质

• 沸点：
  250.8±23.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 3-pyrrolidinobutyrate 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 乙醚 为溶剂， 生成 Dimethyl-carbamic acid 3-pyrrolidin-1-yl-butyl ester
  参考文献：
  名称：

  Carbamoylcholine homologs: synthesis and pharmacology at nicotinic acetylcholine receptors

  摘要：

  In a recent study, racemic 3-(N,N-dimethylamino)butyl-N,N-dimethylcarbamate (1) was shown to be a potent agonist at neuronal nicotinic acetylcholine receptors with a high selectivity for nicotinic over muscarinic acetylcholine receptors [Mol. Pharmacol. 64 (2003) 865-875]. Here we present the synthesis and pharmacological characterization of a series of analogs of 1, where the methyl group at C-3 has been replaced by different alkyl substituents. Ring systems have been incorporated into the carbon backbone of some of the molecules, or the amino group has been build into ring systems. Furthermore, the (+)- and (-)-enantiomers of I have been separated, and X-ray crystallography has revealed that (-)-1 possesses (S)-configuration. The compounds have been characterized pharmacologically at recombinant nicotinic receptor subtypes. The structure-activity relationship study has provided valuable insight into the mode of interactions of I and its analogs with neuronal nicotinic acetylcholine receptors. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2004.06.038
• 作为产物：
  描述：

  (Z)-3-(吡咯烷-1-基)2-丁酸乙酯 在 三乙酰氧基硼氢化钠 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以84%的产率得到Ethyl 3-pyrrolidinobutyrate
  参考文献：
  名称：

  Chemo- and Diastereoselective Reduction of .beta.-Enamino Esters: A Convenient Synthesis of Both cis- and trans-.gamma.-Amino Alcohols and .beta.-Amino Esters

  摘要：

  Convenient procedures for the chemo- and diastereoselective reduction of beta-enamino esters 1 are described. Both cis- and trans-gamma-amino alcohols 2 or beta-amino esters 3 can be prepared by reduction of beta-enamino esters 1, readily available starting materials, with the use of inexpensive reagents Nali-PrOH or NaHbB(OAc)(3)/AcOH, respectively, and the appropriate reduction conditions. The mechanisms and diastereoselectivities for the reductions are discussed. The relative configurations and conformations of the diastereoisomeric gamma-amino alcohols 2 and beta-amino esters 3 obtained are established by H-1 and C-13 NMR study and unequivocally set by their cyclic derivatives tetrahydro-1,3-oxazines 4.

  DOI：

  10.1021/jo00097a039

文献信息

• 3- Or 4-monosubstituted phenol derivatives useful as H3 ligands
  申请人：Warner-Lambert Company LLC

  公开号：EP1593679A1

  公开（公告）日：2005-11-09

  The invention relates to 3- or 4-monosubstituted phenol derivatives and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such derivatives. Said 3- or 4-monosubstituted phenol derivatives are H3 ligands and are useful in numerous diseases, disorders and conditions, in particular inflammatory, allergic and respiratory diseases, disorders and conditions.

  这项发明涉及3-或4-单取代酚衍生物，以及用于制备、制备中间体、含有和使用这些衍生物的过程。所述的3-或4-单取代酚衍生物是H3配体，在许多疾病、紊乱和状况中非常有用，特别是炎症性、过敏性和呼吸系统疾病、紊乱和状况。
• Screening and characterization of a diverse panel of metagenomic imine reductases for biocatalytic reductive amination
  作者：James R. Marshall、Peiyuan Yao、Sarah L. Montgomery、James D. Finnigan、Thomas W. Thorpe、Ryan B. Palmer、Juan Mangas-Sanchez、Richard A. M. Duncan、Rachel S. Heath、Kirsty M. Graham、Darren J. Cook、Simon J. Charnock、Nicholas J. Turner

  DOI：10.1038/s41557-020-00606-w

  日期：2021.2

  identification of new biocatalysts for asymmetric synthesis remains both a challenge and a rate-limiting step in enzyme discovery. Biocatalytic strategies for the synthesis of chiral amines are increasingly attractive and include enzymatic asymmetric reductive amination, which offers an efficient route to many of these high-value compounds. Here we report the discovery of over 300 new imine reductases

  寻找更快、更简单的方法来筛选蛋白质序列空间，以鉴定用于不对称合成的新生物催化剂，仍然是酶发现中的挑战和限速步骤。合成手性胺的生物催化策略越来越有吸引力，其中包括酶促不对称还原胺化，这为许多这些高价值化合物提供了有效的途径。在这里，我们报告了 300 多种新的亚胺还原酶的发现，以及可用于筛选的大量（384 种酶）且序列多样化的亚胺还原酶组的生产。我们还报告了一种简便的高通量筛选的开发，以询问它们的活动。通过这种方法，我们鉴定了能够接受结构要求高的酮和胺的亚胺还原酶生物催化剂，其中包括通过动态动力学拆分过程制备合成N-取代的β-氨基酯衍生物，具有优异的产率和立体化学纯度。
• Lanthanoid Triflate Catalyzed Conjugate Addition of Amines to α, β-Unsaturated Esters. A Facile Route to Optically Active β-Lactam
  作者：Seijiro Matsubara、Masahito Yoshioka、Kiitiro Utimoto

  DOI：10.1246/cl.1994.827

  日期：1994.5

  Catalytic amount of lanthanoid(III) triflates promoted the conjugate addition of amines to 2-alkenoic acid esters to give β-amino esters. The reaction of benzylamine with α,β-unsaturated esters containing a stereogenic center at γ-position proceeded diastereoselectivity to yield optically active β-lactam precursors.

  催化量的镧系元素(III)三氟甲磺酸酯促进胺与2-链烯酸酯的共轭加成，得到β-氨基酯。苄胺与 γ 位具有立构中心的 α,β-不饱和酯发生非对映选择性反应，生成光学活性的 β-内酰胺前体。
• 3- or 4-monosubstituted phenol and thiophenol derivatives useful as H3 ligands
  申请人：Bernardelli Patrick

  公开号：US20050267095A1

  公开（公告）日：2005-12-01

  The invention relates to 3- or 4-monosubstituted phenol and thiophenol derivatives of formula (I) and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such derivatives. Said 3- or 4-monosubstituted phenol and thiophenol derivatives are H 3 ligands and are useful in numerous diseases, disorders and conditions, in particular inflammatory, allergic and respiratory diseases, disorders and conditions.

  本发明涉及公式(I)的3-或4-单取代苯酚和硫代苯酚衍生物，以及用于制备这些衍生物的中间体、含有这些衍生物的组合物和这些衍生物的用途的过程。所述的3-或4-单取代苯酚和硫代苯酚衍生物是H3配体，在许多疾病、失调和病况中特别有用，特别是在炎性、过敏和呼吸系统疾病、失调和病况中。
• 3- or 4-monosubtituted phenol and thiophenol derivatives useful as H3 ligands
  申请人：Pfizer, Inc

  公开号：US07456164B2

  公开（公告）日：2008-11-25

  The invention relates to 3- or 4-monosubstituted phenol and thiophenol derivatives of formula (I) and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such derivatives. Said 3- or 4-monosubstituted phenol and thiophenol derivatives are H3 ligands and are useful in numerous diseases, disorders and conditions, in particular inflammatory, allergic and respiratory diseases, disorders and conditions.

  本发明涉及式（I）的3或4-单取代苯酚和噻吩酚衍生物，以及用于制备、制备中间体、含有和使用此类衍生物的组合物的过程。所述的3或4-单取代苯酚和噻吩酚衍生物是H3配体，可用于许多疾病、障碍和病况，特别是炎症性、过敏性和呼吸系统疾病、障碍和病况。