(S)-1-BOC-2-乙酰基-吡咯烷 | 91550-08-2

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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)-1-BOC-2-乙酰基-吡咯烷
• 英文名称: tert-butyl (2S)-2-acetylpyrrolidine-1-carboxylate
• CAS: 91550-08-2
• 化学式: C₁₁H₁₉NO₃
• mdl: MFCD16308624
• 分子量: 213.277
• InChiKey: NNCPMJHKYIRKSA-VIFPVBQESA-N

物化性质

• 熔点：
  46-49 °C
• 沸点：
  293.8±33.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P280
• 危险性描述：
  H302,H317
• 储存条件：
  存储条件：2-8°C，密封保存，置于干燥处。

反应信息

• 作为反应物：
  描述：

  (S)-1-BOC-2-乙酰基-吡咯烷 在 盐酸 、 叔丁基过氧化氢 、 selenium(IV) oxide 、 diiron nonacarbonyl 、 一氧化碳 、 sodium hydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 为溶剂， 反应 64.25h， 生成 倒千里光裂醇
  参考文献：
  名称：

  通过π-烯丙基三羰基铁内酰胺配合物合成生物碱（-）-三碘三环己烷和（-）-异维甲酸。

  摘要：

  描述了吡咯烷核生物碱（-）-三碘三环烷（1）和（-）-异戊烯醇（2）的新型合成方法。关键步骤包括将脯氨酸衍生的氨基甲酸酯（10）转化为π-烯丙基三羰基铁内酰胺复合物（4）并对其进行彻底的羰基化，以得到关键的中间体γ-内酰胺（3）。内酰胺（3）已通过标准方法转化为标题化合物。

  DOI：

  10.1016/0040-4039(91)85056-b
• 作为产物：
  描述：

  (S)-N-Boc-吡咯烷-2-甲醛 N-(叔丁氧羰基)-L-脯氨醛 在 pyridine-SO3 complex 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 (S)-1-BOC-2-乙酰基-吡咯烷
  参考文献：
  名称：

  4-Phenylbutanoyl-2( S )-acylpyrrolidines and 4-phenylbutanoyl- l -prolyl-2( S )-acylpyrrolidines as prolyl oligopeptidase inhibitors

  摘要：

  New 4-phenylbutanoyl-2(S)-acylpyrrolidines and 4-phenylbutanoyl-L-prolyl-2(S)-acylpyrrolidines were synthesized. Their inhibitory activity against prolyl oligopeptidase from pig brain was tested in vitro. In the series of 4-phenylbutanoyl-2(S)-acylpyrrolidines, the cyclopentanecarbonyl and benzoyl derivatives were the best inhibitors having IC50 values of 30 and 23 nM, respectively. This series of compounds shows that that P1 pyrrolidine ring, which is common in most POP inhibitors, can be replaced by either a cyclopentyl ring or a phenyl ring, causing only a slight decrease in the inhibitory activity. In the series of 4-phenylbutanoyl-L-prolyl-2(S)- acyl-pyrrolidines, the cyclopentanecarbonyl and benzoyl derivatives were not as active as in the series of 4-phenylbutanoyl-2(S)-acylpyrrolidines, The hydroxyacetyl derivative did however show high inhibitors activity. This compound is structurally similar to JTP-4819, which is one of the most potent prolyl oligopeptidase inhibitors. The acyl group in the two series of new compounds seems to bind to different sites of the enzyme, since the second series of ne compounds did not show the same cyclopentanecarbonyl or benzoyl specificity as the first series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00061-5
• 作为试剂：
  描述：

  1-萘甲醛 、 苯乙炔 在 titanium(IV) isopropylate 、 diethylzinc 、 (S)-1-BOC-2-乙酰基-吡咯烷 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 19.0h， 生成 (R)-1-naphthalen-1-yl-3-phenyl-prop-2-yn-1-ol
  参考文献：
  名称：

  Boc-l-proline as a new chiral ligand for enantioselective phenylacetylene addition to aromatic aldehydes

  摘要：

  The N-terminal protected amino acid (BOC-L-proline) is a chiral ligand for the enantioselective phenylacetylene addition to aromatic aldehydes, thus expanding the utility of the simplest enzyme, proline, in asymmetric catalysis. Good yields and enantioselectivities (up to 77% ee) were achieved. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.005

文献信息

• Arylation of α-Chiral Ketones by Palladium-Catalyzed Cross-Coupling Reactions of Tosylhydrazones with Aryl Halides
  作者：José Barluenga、María Escribano、Fernando Aznar、Carlos Valdés

  DOI：10.1002/anie.201003450

  日期：2010.9.10

  Arylation of ketones with preservation of the chirality in configurationally unstable α‐chiral ketones has been achieved by the palladium‐catalyzed cross‐coupling reaction between tosylhydrazones and aryl halides (see scheme; Boc=tert‐butoxycarbonyl, Ts=4‐toluenesulfonyl). The regioselectivity in the β‐hydride elimination step is key for the retention of configuration.

  爸爸是一个罗林酮：在构型上不稳定的α手性酮与手性的保存酮的芳基化已被钯催化交叉偶联甲苯磺酰腙和芳基卤化物之间的反应（参见方案来实现将Boc =叔丁氧羰基中，Ts = 4-甲苯磺酰基）。β-氢化物消除步骤中的区域选择性是保持构型的关键。
• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR SYNTHESIS<br/>[FR] COMPOSÉS, COMPOSITIONS ET PROCÉDÉS DE SYNTHÈSE
  申请人：WAVE LIFE SCIENCES LTD

  公开号：WO2018237194A1

  公开（公告）日：2018-12-27

  The present disclosure, among other things, provides technologies for synthesis, including reagents and methods for stereoselective synthesis. In some embodiments, the present disclosure provides compounds useful as chiral auxiliaries. In some embodiments, the present disclosure provides reagents and methods for oligonucleotide synthesis. In some embodiments, the present disclosure provides reagents and methods for chirally controlled preparation of oligonucleotides. In some embodiments, technologies of the present disclosure are particularly useful for constructing challenging internucleotidic linkages, providing high yields and stereoselectivity.

  本公开内容提供了合成技术，包括用于立体选择性合成的试剂和方法。在某些实施例中，本公开内容提供了作为手性辅助剂有用的化合物。在某些实施例中，本公开内容提供了用于寡核苷酸合成的试剂和方法。在某些实施例中，本公开内容提供了用于手性控制寡核苷酸制备的试剂和方法。在某些实施例中，本公开内容的技术特别适用于构建具有挑战性的核苷酸间连接，提供高产率和立体选择性。
• Total Synthesis of the Highly <i>N-</i>Methylated Acetylene-Containing Anticancer Peptide Jahanyne
  作者：Andrew Siow、George Opiyo、Iman Kavianinia、Freda F. Li、Daniel P. Furkert、Paul W. R. Harris、Margaret A. Brimble

  DOI：10.1021/acs.orglett.7b03925

  日期：2018.2.2

  The first total synthesis of the highly N-methylated acetylene-containing lipopeptide jahanyne, an apoptosis-inducing natural product from marine cyanobacteria, is reported. A late-stage solution-phase coupling enabled introduction of the C-terminal ketone pyrrolidine moiety. A modified Fmoc solid-phase synthesis strategy was adopted to effectively couple multiple sterically hindered N-methylated amino

  报道了高度N-甲基化的乙炔的脂肽jahanyne的首次全合成，这是一种来自海洋蓝细菌的诱导细胞凋亡的天然产物。后期溶液相偶联使得能够引入C-末端酮吡咯烷部分。采用了改良的Fmoc固相合成策略，可以有效地偶联多个空间受阻的N-甲基化氨基酸，同时抑制差向异构化。总的合成已经证实了天然茉莉炔酮的提议的绝对构型的确认。
• Graphitic Carbon Nitride Polymer as a Recyclable Photoredox Catalyst for Decarboxylative Alkynylation of Carboxylic Acids
  作者：Jiaqi Guo、Yating Wang、Yuhang Li、Kailin Lu、Shihui Liu、Wei Wang、Yongqiang Zhang

  DOI：10.1002/adsc.202000777

  日期：2020.9.21

  Visible‐light‐induced heterogeneous photocatalysis for decarboxylative alkynylation has been performed. The using of cheap, metal‐free and recyclable graphitic carbon nitride (g‐C3N4) as the photoredox catalyst in the process enables the facile transformation of a variety of carboxylic acids into structurally diverse alkyne‐containing molecular architectures under mild and environmentally‐benign conditions

  可见光诱导的非均相光催化脱羧炔基反应。使用便宜，无金属且可回收的石墨氮化碳（g ‐ C 3 N 4）作为该过程中的光氧化还原催化剂，可以在温和和环境友好的条件下将多种羧酸轻松转化为结构多样的含炔分子结构。明显地，反应系统的非均质性质允许催化剂在多次运行中的回收和再利用而不损失反应性。光催化反应也可以以连续流动的方式进行并按比例放大至克级。此外，该策略在未活化烯烃的1，2氨基炔基化中的应用进一步凸显了该策略的制备能力。
• Hepatitis C Virus Inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US20130183269A1

  公开（公告）日：2013-07-18

  The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.

  本公开涉及抗病毒化合物，更具体地涉及能够抑制丙型肝炎病毒（HCV）编码的NS5A蛋白功能的化合物组合，包括这种组合的组成物，以及抑制NS5A蛋白功能的方法。