ethyl N-(phenylmethoxycarbonyl)-(L)-prolinate | 51207-69-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl N-(phenylmethoxycarbonyl)-(L)-prolinate
• 英文别名: 1,2-pyrrolidinedicarboxylic acid 2-ethyl 1-(phenylmethyl) ester；(S)-N-carbobenzyloxyprolineethyl ester；1-benzyl 2-ethyl (2S)-pyrrolidine-1,2-dicarboxylate；1-Benzyl 2-ethyl (S)-pyrrolidine-1,2-dicarboxylate；1-O-benzyl 2-O-ethyl (2S)-pyrrolidine-1,2-dicarboxylate
• CAS: 51207-69-3
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: PKBGOOMPQHCKHH-ZDUSSCGKSA-N

物化性质

• 沸点：
  388.5±42.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl N-(phenylmethoxycarbonyl)-(L)-prolinate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 以47%的产率得到(2S)-N-苄氧羰基-2-吡咯烷甲醛
  参考文献：
  名称：

  Synthetic studies towards proline amide isosteres, potentially useful molecules for biological investigations

  摘要：

  2-Ethenylpyrrolidine derivative 8b was prepared from N-protected proline ethyl ester 6b. Bromofluorination of 8b with NBS-Bu(4)NF/2HF gave a 1:1 regioisomeric mixture, 9b and 10b (X = Br). Dehydrobromination of 9b and 10b with t-BuOK produced a fluoroolefin 11 and a proline amide isostere model 12, respectively. Deprotection of the Z group in 12 was attempted by treatment with CF3COOH. Although formation of the useful molecule in pseudopeptide synthesis, 13, was observed as checked by NMR spectra, it seemed to decompose slowly during purification procedure to give a mixture of flourine-free compounds.

  DOI：

  10.1016/0040-4020(95)00910-z
• 作为产物：
  描述：

  L-脯氨酸 在 sodium hydroxide 、 (+)-10-camphorsulfonic acid 作用下， 以 水 为溶剂， 反应 33.5h， 生成 ethyl N-(phenylmethoxycarbonyl)-(L)-prolinate
  参考文献：
  名称：

  Synthetic studies towards proline amide isosteres, potentially useful molecules for biological investigations

  摘要：

  2-Ethenylpyrrolidine derivative 8b was prepared from N-protected proline ethyl ester 6b. Bromofluorination of 8b with NBS-Bu(4)NF/2HF gave a 1:1 regioisomeric mixture, 9b and 10b (X = Br). Dehydrobromination of 9b and 10b with t-BuOK produced a fluoroolefin 11 and a proline amide isostere model 12, respectively. Deprotection of the Z group in 12 was attempted by treatment with CF3COOH. Although formation of the useful molecule in pseudopeptide synthesis, 13, was observed as checked by NMR spectra, it seemed to decompose slowly during purification procedure to give a mixture of flourine-free compounds.

  DOI：

  10.1016/0040-4020(95)00910-z

文献信息

• A Simple, Efficient, Catalyst-Free and Solvent-Less Microwave-Assisted Process for N-Cbz Protection of Several Amines
  作者：Aouf, Zineb、Mansouri, Rachida、Lakrout, Salah、Berredjem, Malika、Aouf, Nour-Eddine

  DOI：10.5012/jkcs.2017.61.4.151

  日期：——

  A simple, green and chemo-selective method for the N-benzyloxycarbonylation of amines, $\beta}$-amino alcohols, $\alpha}$-amino esters and sulfonamides has been developed under microwave irradiation. Good to excellent yields of the N-benzyloxycarbamates compounds were obtained in short times without any side products.

  一种简单、绿色且选择性强的氨基、β-氨基醇、α-氨基酯和磺酰胺的N-苄氧羰基化方法已在微波辐射下开发。该方法在短时间内获得了良好到优秀的N-苄氧羰基氨基酸酯化合物产率，并且没有任何副产物。
• Electrochemical Deallylation of α-Allyl Cyclic Amines and Synthesis of Optically Active Quaternary Cyclic Amino Acids
  作者：Peter G. Kirira、Masami Kuriyama、Osamu Onomura

  DOI：10.1002/chem.200903512

  日期：2010.4.6

  Electrochemical oxidation of α‐allylated and α‐benzylated N‐acylated cyclic amines by using a graphite anode easily affords the corresponding α‐methoxylated products with up to 76 % yield. Ease of oxidation was affected by the type of electrode, the size of cyclic amine, and the nature of the protecting group. This method was successfully applied to the synthesis of optically active N‐acylated α‐alkyl‐α‐amino

  通过使用石墨阳极对α-烯丙基化和α-苄基化N-酰化的环状胺进行电化学氧化，可以轻松获得相应的α-甲氧基化产物，收率高达76％。电极的类型，环胺的大小和保护基的性质会影响氧化的难易程度。该方法已成功应用于合成具有高达99％ee的旋光性N酰化的α-烷基-α-氨基酸酯 。
• 用于治疗精神分裂症、双相障碍、认知损害和重度抑郁障碍的非典型抗精神病药和NMDA调节剂的药物组合
  申请人：西北大学

  公开号：CN108601814A

  公开（公告）日：2018-09-28

  本公开的特征在于NMDA调节剂和非典型抗精神病药的组合。本公开提供例如治疗有需要的患者的精神分裂症、双相障碍和/或认知损害病症的方法，其包括施用例如雷帕替奈和非典型抗精神病药。
• Pro-drugs of A2B Adenosine Receptor Antagonists
  申请人：Kalla Rao

  公开号：US20100056538A1

  公开（公告）日：2010-03-04

  Disclosed are prodrugs of A 2B adenosine receptor antagonists, and their use in treating mammals for various disease states.

  本发明涉及A2B腺苷受体拮抗剂的前药，以及它们在治疗各种疾病状态的哺乳动物中的应用。
• PRODRUGS OF A2B ADENOSINE RECEPTOR ANTAGONISTS
  申请人：Kalla Rao

  公开号：US20110160162A1

  公开（公告）日：2011-06-30

  Disclosed are prodrugs of A 2B adenosine receptor antagonists, and their use in treating mammals for various disease states.

  本发明涉及A2B腺苷受体拮抗剂的前药，以及它们在治疗哺乳动物的各种疾病状态方面的应用。