1-吡咯烷羧酸,2-苯甲酰-,乙基酯,(S)- | 106202-17-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-吡咯烷羧酸,2-苯甲酰-,乙基酯,(S)-
• 英文名称: ethyl (S)-2-benzoylpyrrolidine-1-carboxylate
• 英文别名: 1-Pyrrolidinecarboxylic acid, 2-benzoyl-, ethyl ester, (S)-；ethyl (2S)-2-benzoylpyrrolidine-1-carboxylate
• CAS: 106202-17-9
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: FRENTXMDXXZFAL-LBPRGKRZSA-N

物化性质

• 沸点：
  370.7±35.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-吡咯烷羧酸,2-苯甲酰-,乙基酯,(S)- 在 氢氧化钾 、 二异丁基氢化铝 作用下， 以 甲醇 为溶剂， 生成 (S)-α-<(R)-pyrrolidin-2-yl>benzyl alcohol
  参考文献：
  名称：

  Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydes using chiral pyrrolidinylmethanols and their metal salts

  摘要：

  DOI：

  10.1021/ja00257a034
• 作为产物：
  描述：

  L-吡咯烷-1,2-二羧酸-1-乙酯 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-吡咯烷羧酸,2-苯甲酰-,乙基酯,(S)-
  参考文献：
  名称：

  （S）脯氨酸的高度立体有规芳构化和α-氨基酮的互补非对映选择性的高度还原。（1 S，2 'S）-和（1 R，2 'S）-苯基（2'-吡咯烷基）甲醇的不对称合成

  摘要：

  旋光性的苏-和赤-苯基（2'-吡咯烷基）甲醇（93-100％对映异构体过量，100％非对映异构体过量）是通过立体有规芳构化由（S）-脯氨酸合成的，随后α的互补非对映选择性还原-氨基酮。

  DOI：

  10.1039/c39860000412

文献信息

• Stereocontrolled Solid-Phase Synthesis of Oligonucleoside<i>H</i>-Phosphonates by an Oxazaphospholidine Approach
  作者：Naoki Iwamoto、Natsuhisa Oka、Terutoshi Sato、Takeshi Wada

  DOI：10.1002/anie.200804408

  日期：2009.1.5

  Stereodefined oligonucleoside H‐phosphonates were synthesized on a solid support using diastereopure nucleoside 3′‐O‐oxazaphospholidine monomers. Several stereodefined backbone‐modified analogues were obtained with the oligonucleoside H‐phosphonates as precursors (see scheme; BPRO=protected nucleobase, DMTr=4,4′‐dimethoxytrityl, Th=thymin‐1‐yl, TfO−=triflate).

  使用非对映体纯核苷3'- O-氧杂氮杂磷啶单体在固体支持物上合成立体定义的寡核苷H-膦酸酯。与寡核苷得到几个stereodefined骨架修饰的类似物ħ -phosphonates作为前体（参见方案;乙PRO =保护的核碱基，将DMTr = 4,4'-二甲氧基三苯甲基，TH =胸腺嘧啶-1-基，TFO - =三氟甲磺酸酯）。
• Diastereoselective Synthesis of (<i>R</i>)-Phenanthrenyl-9yl-[(<i>S</i>)-pyrrolidin-2yl)] Methanol
  作者：Alessio Russo、Tiziana Fuoco、Alessandra Lattanzi

  DOI：10.1080/00397911.2011.609303

  日期：2013.2.1

  Abstract A four-step synthesis of sterically demanding (R)-phenanthren-9-yl-[(S)-pyrrolidin-2-yl] methanol has been easily accomplished starting from L-proline in high diastereoselectivity. These compounds are potentially useful ligands in metal-catalyzed reactions and organocatalysts. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications®

  摘要 以高非对映选择性为原料，以 L-脯氨酸为原料，可以很容易地通过四步合成空间要求高的 (R)-菲-9-基-[(S)-吡咯烷-2-基] 甲醇。这些化合物是金属催化反应和有机催化剂中潜在有用的配体。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• Highly stereospecific arylation of (S)proline and complementary highly diastereoselective reduction of the α-amino ketone. Asymmetric synthesis of (1S,2′S)- and (1R,2′S)-phenyl(2′-pyrrolidinyl)methanol
  作者：Kenso Soai、Atsuhiro Ookawa

  DOI：10.1039/c39860000412

  日期：——

  Both optically active threo- and erythro-phenyl(2′-pyrrolidinyl)methanol (93–100% enantiomeric excess, 100% diastereoisomeric excess) were synthesised from (S)-proline by a stereospecific arylation and the subsequent complementary diastereoselective reduction of the α-amino ketone.

  旋光性的苏-和赤-苯基（2'-吡咯烷基）甲醇（93-100％对映异构体过量，100％非对映异构体过量）是通过立体有规芳构化由（S）-脯氨酸合成的，随后α的互补非对映选择性还原-氨基酮。
• Inhibition of 14-3-3/Tau by Hybrid Small-Molecule Peptides Operating via Two Different Binding Modes
  作者：Sebastian A. Andrei、Femke A. Meijer、João Filipe Neves、Luc Brunsveld、Isabelle Landrieu、Christian Ottmann、Lech-Gustav Milroy

  DOI：10.1021/acschemneuro.8b00118

  日期：2018.11.21

  Current molecular hypotheses have not yet delivered marketable treatments for Alzheimer's disease (AD), arguably due to a lack of understanding of AD biology and an overreliance on conventional drug modalities. Protein-protein interactions (PPIs) are emerging drug targets, which show promise for the treatment of, e.g., cancer, but are still underexploited for treating neurodegenerative diseases. 14-3-3 binding to phosphorylated Tau is a promising PPI drug target based on its reported destabilizing effect on microtubules, leading to enhanced neurofibrillary tangle formation as a potential cause of AD-related neurodegeneration. Inhibition of 14-3-3/Tau may therefore be neuroprotective. Previously, we reported the structure-guided development of modified peptide inhibitors of 14-3-3/Tau. Here, we report further efforts to optimize the binding mode and activity of our modified Tau peptides through a combination of chemical synthesis, biochemical assays, and X-ray crystallography. Most notably, we were able to characterize two different high-affinity binding modes, both of which inhibited 14-3-3-binding to full-length PKA-phosphorylated Tau protein in vitro as measured by NMR spectroscopy. Our findings, besides producing useful tool inhibitor compounds for studying 14-3-3/Tau, have enhanced our understanding of the molecular parameters for inhibiting 14-3-3/Tau, which are important milestones toward the establishment of our 14-3-3 PPI hypothesis.
• OOKAWA, ATSUHIRO;SOAI, KENSO, J. CHEM. SOC. PERKIN TRANS.,(1987) N 7, 1465-1471
  作者：OOKAWA, ATSUHIRO、SOAI, KENSO

  DOI：——

  日期：——