N-CBz-4-exo-methylene-L-proline ethyl ester | 169820-06-8

• 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: N-CBz-4-exo-methylene-L-proline ethyl ester
• 英文别名: N-CBz-4-exomethylene-L-proline ethyl ester；N-Cbz-4-exomethylene-L-proline ethyl ester；1-O-benzyl 2-O-ethyl (2S)-4-methylidenepyrrolidine-1,2-dicarboxylate
• CAS: 169820-06-8
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: QRYJTBYZQXCSJW-AWEZNQCLSA-N

物化性质

• 沸点：
  399.4±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  N-CBz-4-exo-methylene-L-proline ethyl ester 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 22.0h， 生成 (4S)-4-甲基-l-脯氨酸
  参考文献：
  名称：

  Nazumazoles A–C, Cyclic Pentapeptides Dimerized through a Disulfide Bond from the Marine Sponge Theonella swinhoei

  摘要：

  A mixture of nazumazoles A-C (1-3) was purified from the extract of the marine sponge Theonella swinhoei. The mixture was eluted as an extraordinarily broad peak in the reversed-phase HPLC. The structures of nazumazoles were determined by interpretation of the NMR data and chemical degradations. Nazumazoles contain one residue each of alanine-derived oxazole and alpha-keto-beta-amino acid residue. Nazumazoles exhibited cytotoxicity against P388 cells.

  DOI：

  10.1021/acs.orglett.5b01020
• 作为产物：
  描述：

  N-Cbz-trans-4-hydroxy-L-proline ethyl ester 在 chromium(VI) oxide 、 dimethyltitanocene 作用下， 以 吡啶 、 二氯甲烷 、 甲苯 为溶剂， 反应 19.0h， 生成 N-CBz-4-exo-methylene-L-proline ethyl ester
  参考文献：
  名称：

  Nazumazoles A–C, Cyclic Pentapeptides Dimerized through a Disulfide Bond from the Marine Sponge Theonella swinhoei

  摘要：

  A mixture of nazumazoles A-C (1-3) was purified from the extract of the marine sponge Theonella swinhoei. The mixture was eluted as an extraordinarily broad peak in the reversed-phase HPLC. The structures of nazumazoles were determined by interpretation of the NMR data and chemical degradations. Nazumazoles contain one residue each of alanine-derived oxazole and alpha-keto-beta-amino acid residue. Nazumazoles exhibited cytotoxicity against P388 cells.

  DOI：

  10.1021/acs.orglett.5b01020

文献信息

• Concise, Stereoselective Route to the Four Diastereoisomers of 4-Methylproline
  作者：Annabel C. Murphy、Maya I. Mitova、John W. Blunt、Murray H. G. Munro

  DOI：10.1021/np070673w

  日期：2008.5.1

  has often been hindered by long reaction sequences or low stereoselectivity in the synthesis leading to reference samples. The preparation of the four diastereoisomers of 4-methylproline by a concise and stereoselective route is presented and features a six-step route with late-stage stereodivergence, good stereoselectivity for both cis- and trans-series (75% and 88% de, respectively), and good overall

  4-甲基脯氨酸（在许多肽类次级代谢产物中发现的一种稀有氨基酸）的完整立体化学特征通常由于合成过程中反应序列长或立体选择性低而受到阻碍，从而导致产生参考样品。介绍了一种通过简明和立体选择的路线制备4-甲基脯氨酸的四种非对映异构体的方法，该方法具有六步路线，具有后期立体发散性，对顺式和反式系列均具有良好的立体选择性（分别为75％和88％de ）和良好的总体产量（累计产量为30-40％）。还提供了有关立体异构体的马菲衍生物的其他数据。
• Thrombin Inhibitors from the Freshwater Cyanobacterium <i>Anabaena compacta</i>
  作者：Andrea Roxanne J. Anas、Takaya Kisugi、Taiki Umezawa、Fuyuhiko Matsuda、Marc R. Campitelli、Ronald J. Quinn、Tatsufumi Okino

  DOI：10.1021/np300282a

  日期：2012.9.28

  Bioassay-guided investigation of the cyanobacterium Anabaena compacta extracts afforded spumigin J (1) and the known thrombin inhibitor spumigin A (2). The absolute configuration of 1 was analyzed by advanced Marfey's methodology. Compounds 1 and 2 inhibited thrombin with EC50 values of 4.9 and 2.1 mu M, and 0.7 and 0.2 mu M in the cathepsin B inhibitory assay, respectively. The MM-GBSA methodology predicted spumigin A with 2S-4-methylproline as the better thrombin inhibitor.