(S)-1-N-苄氧羰基-2-氰基吡咯烷 | 63808-36-6

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-1-N-苄氧羰基-2-氰基吡咯烷
• 中文别名: (S)-1-n-cbz-2-氰基吡咯烷；(S)-1-Cbz-2-氰基-吡咯烷
• 英文名称: (2S)-2-cyanopyrrolidine-1-carboxylic acid benzyl ester
• 英文别名: (-)-(S)-2-cyano-pyrrolidine-1-carboxylic acid benzyl ester；(S)-1-N-Cbz-2-cyano-pyrrolidine；benzyl (2S)-2-cyanopyrrolidine-1-carboxylate
• CAS: 63808-36-6
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: AUVGQGIWVNDVSL-LBPRGKRZSA-N

物化性质

• 熔点：
  37-39 °C
• 沸点：
  403.6±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H319
• 储存条件：
  2-8°C，惰性气体

反应信息

• 作为反应物：
  描述：

  (S)-1-N-苄氧羰基-2-氰基吡咯烷 在 decamethylrhenocene 盐酸 、 甲酸 作用下， 以 水 、 甲苯 为溶剂， 110.0 ℃ 、1.4 MPa 条件下， 反应 35.0h， 生成 S-(-)-烟碱
  参考文献：
  名称：

  Synthesis of 1-Substituted 2-[(2S)-2-Pyrrolidinyl]pyridine from L-Proline

  摘要：

  据报道，该研究以 L-脯氨酸为原料合成了具有光学活性的 2-[(2S)-2-吡咯烷基]吡啶。该化合物可进一步烷基化，得到相应的 N-甲基和 N-苄基吡咯烷衍生物。

  DOI：

  10.1055/s-1990-27109
• 作为产物：
  描述：

  (2S)-N-苄氧羰基-2-吡咯烷甲醛 在 ammonium hydroxide 、 碘 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到(S)-1-N-苄氧羰基-2-氰基吡咯烷
  参考文献：
  名称：

  Microwave-Assisted One-Pot Tandem Reactions for Direct Conversion of Primary Alcohols and Aldehydes to Triazines and Tetrazoles in Aqueous Media

  摘要：

  A series of primary alcohols and aldehydes were treated with iodine in ammonia water under microwave irradiation to give the intermediate nitriles, which without isolation underwent [2 + 3] cycloadditions with dicyandiamide and sodium azide to afford high yields of the corresponding triazines and tetrazoles, including the alpha-amino- and dipeptidyl tetrazoles in high optical purity.

  DOI：

  10.1021/jo0625352

文献信息

• Fast Cyclization of a Proline‐Derived Self‐Immolative Spacer Improves the Efficacy of Carbamate Prodrugs
  作者：Alberto Dal Corso、Valentina Borlandelli、Cristina Corno、Paola Perego、Laura Belvisi、Luca Pignataro、Cesare Gennari

  DOI：10.1002/anie.201916394

  日期：2020.3.2

  spacers are sophisticated chemical constructs designed for molecular delivery or material degradation. We describe herein a (S)-2-(aminomethyl)pyrrolidine SI spacer that is able to release different types of anticancer drugs (possessing either a phenolic or secondary and tertiary hydroxyl groups) through a fast cyclization mechanism involving carbamate cleavage. The high efficiency of drug release obtained

  自焚（SI）间隔基是设计用于分子传递或材料降解的复杂化学结构。我们在本文中描述了（S）-2-（氨基甲基）吡咯烷SI间隔基，其能够通过涉及氨基甲酸酯裂解的快速环化机制释放不同类型的抗癌药物（具有酚或仲和叔羟基基团）。与同类型的常用间隔物相比，发现通过这种间隔物获得的高效药物释放对蛋白酶敏感性前药的体外细胞毒性活性是有益的。这些发现扩大了降解设备的范围，对高效交付平台的未来发展至关重要。
• Sulfonamide lactam inhibitors of FXa and method
  申请人：Bristol-Myers Squibb Company

  公开号：US06555542B1

  公开（公告）日：2003-04-29

  Sulfonamide lactams of the following formula wherein X, R1, R2, R3, R4, R4a, R5, R5a, R6, R6a, R7 and R8 are as described herein, are provided which inhibitors of Factor Xa and are useful as anticoagulants in the treatment of cardiovascular diseases associated with thromboses.

  以下式中X、R1、R2、R3、R4、R4a、R5、R5a、R6、R6a、R7和R8如本文所述，提供了一种抑制因子Xa的磺胺酰胺内酰胺，可用作抗凝剂，用于治疗与血栓相关的心血管疾病。
• Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions
  作者：Alexander J. A. Cobb、David M. Shaw、Deborah A. Longbottom、Johan B. Gold、Steven V. Ley

  DOI：10.1039/b414742a

  日期：——

  Tetrazole and acylsulfonamide organocatalysts derived from proline have been synthesised and applied to the asymmetric Mannich, nitro-Michael and aldol reactions to give results that are superior to the proline-catalysed counterpart.

  已合成了衍生自脯氨酸的四唑和酰基磺酰胺有机催化剂，并将其应用于不对称的曼尼希，硝基迈克尔和醛醇缩合反应，所得到的结果优于脯氨酸催化的对应物。
• 5-Pyrrolidin-2-yltetrazole: A New, Catalytic, More Soluble Alternative to ­Proline in an Organocatalytic Asymmetric Mannich-type Reaction
  作者：Steven V. Ley、Alexander J. Cobb、David M. Shaw

  DOI：10.1055/s-2004-817745

  日期：——

  A Mannich-type addition of ketones to N-PMP protected α-imino ethyl glyoxalate is catalyzed by a new proline analogue, 5-pyrrolidin-2-yltetrazole 1. The new organocatalyst has significant advantage over its parent in that it can be used in non-polar solvents without loss of enantioselectivity.

  新的吡咯烷-2-基四唑类似物5作为催化剂，促进了酮类物质对N-PMP保护的α-亚氨基乙基乙二醛酸盐的曼尼希型加成反应。这种新型有机催化剂相对其母体化合物具有显著优势，即在非极性溶剂中使用时，不会损失对映选择性。
• Modular syntheses of oxazolinylamine ligands and characterization of group 10 metal complexes
  作者：Christine A Caputo、Florentino d S Carneiro、Michael C Jennings、Nathan D Jones

  DOI：10.1139/v06-188

  日期：2007.2.1

  The syntheses of aminoalkyloxazoline and pyrrolidinyloxazoline ligands, each of which bear a pair of chiral centres, by both known and new routes are reported. Variable temperature NMR studies show that the known stepwise syntheses of the pyrrolidinyl compounds are not complicated by epimerization; however, coordination of one of the aminoalkyl derivatives to Pt(II) under conditions of prolonged heating to 80 °C does give mixtures of diastereomeric N,N ′-chelated complexes that result from inversion of the chiral centre associated with the aminoalkyl fragment. A new synthesis of pyrrolidinyloxazoline ligands that involves the Zn-catalyzed cyclization of Cbz-protected 2-cyanopyrrolidine and β-amino alcohols is also reported. This procedure offers the advantages of economy, shorter time, and fewer purification steps over the previously reported synthesis. In addition, the crystal structure of an enantiopure Pd(II) complex of an N,N ′-chelated pyrrolidinyloxazoline is disclosed. This compound has a pseudo-C₂ axis of symmetry, which may make it suitable for asymmetric catalytic applications.Key words: chiral ligands, ligand design, oxazolines, variable temperature NMR spectroscopy, asymmetric catalysis, coordination compounds, palladium, platinum

  报告采用已知路线和新路线合成了氨基烷基恶唑啉和吡咯烷基恶唑啉配体，每种配体都带有一对手性中心。变温核磁共振研究表明，已知的吡咯烷基化合物的逐步合成过程不会因表聚而复杂化；然而，在长时间加热至 80 °C 的条件下，将其中一种氨基烷基衍生物与 Pt(II) 配位，确实会产生非对映的 N,N′-螯合复合物混合物，这是因为与氨基烷基片段相关的手性中心发生了反转。此外，还报道了一种吡咯烷基噁唑啉配体的新合成方法，该方法涉及 Zn 催化的 Cbz 保护的 2-氰基吡咯烷和 β-氨基醇的环化。与之前报道的合成方法相比，该方法具有经济、时间短、纯化步骤少等优点。此外，还公开了一种 N,N′-螯合吡咯烷基噁唑啉的对映体纯 Pd(II) 复合物的晶体结构。关键词：手性配体；配体设计；噁唑啉；变温核磁共振光谱；不对称催化；配位化合物；钯；铂