(S)-3-甲基吡咯烷 | 69498-25-5

• 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: (S)-3-甲基吡咯烷
• 英文名称: (S)-3-methyl pyrrolidine
• 英文别名: (S)-3-Methylpyrrolidine；(3S)-3-methylpyrrolidine
• CAS: 69498-25-5
• 化学式: C₅H₁₁N
• 分子量: 85.149
• InChiKey: KYINPWAJIVTFBW-YFKPBYRVSA-N

物化性质

• 沸点：
  100 °C
• 密度：
  0.812

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-氟吡啶-N-氧化物 、 (S)-3-甲基吡咯烷 在 碳酸氢钠 作用下， 以 水 为溶剂， 生成 2-((S)-3-Methyl-pyrrolidin-1-yl)-pyridine 1-oxide
  参考文献：
  名称：

  Bettoni, Giancarlo; Cellucci, Carla, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1541 - 1543

  摘要：

  DOI：
• 作为产物：
  描述：

  (3S,6S,7aR)-6-Methyl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 30.0h， 生成 (S)-3-甲基吡咯烷
  参考文献：
  名称：

  A Synthesis of Enantiomerically Pure 3- and 3,3-Disubstituted Pyrrolidines

  摘要：

  Enantiomerically pure bicyclic lactam 1, derived from (S)-phenylglycinol, underwent diastereoselective mono- and dialkylation affording substituted lactams 2 and 3 bearing tertiary and quaternary stereocenters. Reduction with LiAlH4 furnished N-(2'-hydroxy-1'-phenylethyl) pyrrolidines 4 which were efficiently debenzylated by catalytic hydrogenolysis to afford enantiomerically pure 3-mono- and 3,3-disubstituted pyrrolidines 5.

  DOI：

  10.1016/s0040-4039(00)79942-4

文献信息

• 2-Aminomethylthieno[3,2- d ]pyrimidin-4(3 H )-ones bearing 3-methylpyrazole hinge binding moiety: Highly potent, selective, and time-dependent inhibitors of Cdc7 kinase
  作者：Osamu Kurasawa、Misaki Homma、Yuya Oguro、Tohru Miyazaki、Kouji Mori、Noriko Uchiyama、Kenichi Iwai、Akihiro Ohashi、Hideto Hara、Sei Yoshida、Nobuo Cho

  DOI：10.1016/j.bmc.2017.04.044

  日期：2017.7

  a serendipitously-identified Cdc7 inhibitor 2b with a 3-methylpyrazole resulted in a 4-fold increase in potency and acceptable kinase selectivity, leading to the identification of thieno[3,2-d]pyrimidin-4(3H)-one as an alternative scaffold. Structure-activity relationship (SAR) study revealed that incorporation of a substituted aminomethyl group into the 2-position improved kinase selectivity. Indeed

  为了提高开发用于癌症治疗的新型Cdc7抑制剂的成功率，我们探索了一种新的化学型，该化学型可以符合以前构建的药效团模型。用3-甲基吡唑取代偶然鉴定出的Cdc7抑制剂2b的吡啶环，其效力和可接受的激酶选择性提高了4倍，从而导致了噻吩并[3,2- d ]嘧啶-4（3）的鉴定H）-一个作为替代支架。结构-活性关系（SAR）研究表明，将取代的氨基甲基基团并入2位可提高激酶的选择性。的确，吡咯烷基甲基衍生物10c是有效的Cdc7抑制剂（IC 50 = 0.70 nM）高选择性（Cdk2 / Cdc7≥14,000，ROCK1 / Cdc7 = 200）。应当注意，10c表现出显着的时间依赖性Cdc7抑制作用，具有缓慢的解离动力学，细胞药效（PD）效应和COLO205生长抑制作用。此外，通过使用Cdc7和Cdk2的蛋白质结构讨论了10c的高激酶选择性的分子基础。
• Catalyst-free photo-induced aerobic radical synthesis of lactams from <i>N</i>-alkenyl trichloroacetamides in 2-methyltetrahydrofuran as the radical initiator under violet light
  作者：Faïza Diaba、Gisela Trenchs

  DOI：10.1039/d3ob01804k

  日期：——

  The first violet light-mediated synthesis of γ- and δ-lactams from N-alkenyl trichloroacetamides is reported in tetrahydrofuran or 2-methyltetrahydrofuran alone. These catalyst and additive-free reactions are achieved with non-anhydrous solvents and under an air atmosphere where the solvent serves as the radical initiator.

  据报道，仅在四氢呋喃或 2-甲基四氢呋喃中，首次通过紫光介导从N-烯基三氯乙酰胺合成 γ-和 δ-内酰胺。这些无催化剂和无添加剂的反应是使用非无水溶剂在空气气氛下实现的，其中溶剂充当自由基引发剂。
• Optimization of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine-5-ylidene)acetamide derivatives as arginine vasopressin V2 receptor agonists and discussion of their binding modes
  作者：Issei Tsukamoto、Hiroyuki Koshio、Masaya Orita、Chikashi Saitoh、Hiroko Yanai-Inamura、Chika Kitada-Nozawa、Eisaku Yamamoto、Takeyuki Yatsu、Shuichi Sakamoto、Shin-ichi Tsukamoto

  DOI：10.1016/j.bmc.2009.10.038

  日期：2009.12.15

  A series of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine-5-ylidene)acetamide derivatives were optimized to achieve potent agonistic activity, both in vitro and in vivo, for the arginine vasopressin V-2 receptor, resulting in the eventual discovery of compound 1g. Molecular modeling of compound 1g with V-2 receptor was also examined to evaluate the binding mode of this series of compounds. (C) 2009 Elsevier Ltd. All rights reserved.
• Ringdahl, Bjoern, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1984, vol. 38, # 2, p. 141 - 152
  作者：Ringdahl, Bjoern

  DOI：——

  日期：——
• Diastereoselective 5-exo-trig radical cyclisation on N-Acryloyl-tetrahydro-1,3-oxazines. A novel approach to enantiopure 3-substituted pyrrolidines
  作者：Celia Andrés、J.Pablo Duque-Soladana、Jesús M. Iglesias、Rafael Pedrosa

  DOI：10.1016/s0040-4039(96)02091-6

  日期：1996.12

  N-Acryloyl-2-(phenylselenomethyl)-tetrahydro-1,3-oxazine 1 generates a carbon-centred radical in the presence of tri-n-butyltin hydride and AIBN. This radical underwent diastereoselective 5-exo-trig cyclisation leading to a mixture of five-membered lactams 2a and 2b (d.e. 68%). Chromatographic separation of the diastereomers and elimination of the chiral auxiliary provided enantiopure (R)-3-methylpyrrolidine in good chemical yield. Copyright (C) 1996 Elsevier Science Ltd