N-(benzyloxycarbonyl)-5-bromonorvaline methyl ester | 167170-11-8

• 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-(benzyloxycarbonyl)-5-bromonorvaline methyl ester
• 英文别名: methyl (2S)-5-bromo-2-(phenylmethoxycarbonylamino)pentanoate
• CAS: 167170-11-8
• 化学式: C₁₄H₁₈BrNO₄
• 分子量: 344.205
• InChiKey: XQIIEJABIINYKY-LBPRGKRZSA-N

物化性质

• 沸点：
  453.3±45.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-5-bromonorvaline methyl ester 在 hydrazine hydrate 作用下， 以 甲醇 为溶剂， 反应 24.75h， 以90%的产率得到(3S)-3-[(benzyloxycarbonyl)amino]-1-amino-piperidin-2-one
  参考文献：
  名称：

  An Access to Aza-Freidinger Lactams and E-Locked Analogs

  摘要：

  Freidinger lactams, possessing a peptide bond configuration locked to 4 are important key elements of conformationally restricted peptidomimetics. In the present work, the C alpha Hi+1 unit has been replaced by N, leading to novel aza-Freidinger lactams. A synthesis to corresponding building blocks and their E-locked analogs is introduced. The versatile buildings blocks reported here are expected to serve as useful elements in peptide synthesis.

  DOI：

  10.1021/ol3030583
• 作为产物：
  描述：

  Z-L-GluOMe 在 N-甲基吗啉 、 sodium tetrahydroborate 、 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.38h， 生成 N-(benzyloxycarbonyl)-5-bromonorvaline methyl ester
  参考文献：
  名称：

  制备光学活性保护脯氨酸的简便新方法

  摘要：

  用四氢呋喃 (THF) 中的氢化钠处理由受保护的 L-谷氨酸制备的 LN 保护的 2-氨基-5-溴戊酸酯，以高产率得到相应的保护 L-脯氨酸。另一方面，2-氨基丁酸衍生物与氢化钠反应得到1-氨基环丙烷-1-羧酸衍生物。

  DOI：

  10.1246/cl.1996.621

文献信息

• Facile New Method for Preparation of Optically Active Protected Proline
  作者：Jun-ichi Yamaguchi、Masaaki Ueki

  DOI：10.1246/cl.1996.621

  日期：1996.8

  Treatment of L-N-protected 2-amino-5-bromopentanoic acid ester, which was prepared from protected L-glutamic acid, with sodium hydride in tetrahydrofuran (THF) proceeded to give the corresponding protected L-proline in high yield. On the other hand, the reaction of 2-aminobutyric acid derivative with sodium hydride gave the 1-aminocyclopropane-1-carboxylic acid derivative.

  用四氢呋喃 (THF) 中的氢化钠处理由受保护的 L-谷氨酸制备的 LN 保护的 2-氨基-5-溴戊酸酯，以高产率得到相应的保护 L-脯氨酸。另一方面，2-氨基丁酸衍生物与氢化钠反应得到1-氨基环丙烷-1-羧酸衍生物。
• Utility of tetrathiomolybdate and tetraselenotungstate: efficient synthesis of cystine, selenocystine, and their higher homologues
  作者：Ramakrishna G. Bhat、Emmanuel Porhiel、Vadivelu Saravanan、Srinivasan Chandrasekaran

  DOI：10.1016/s0040-4039(03)01222-x

  日期：2003.7

  Efficient synthesis of cystine, selenocystine, and their higher homologues like homo and bishomo amino acid derivatives from natural amino acid derivatives using tetrathiomolybdate and tetraselenotungstate reagents under mild and neutral conditions is reported. The generality of the reaction has been studied by capping various groups to amino and carboxyl components of canonical amino acids. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Azacycle synthesis via radical cyclization of β-aminoacrylates
  作者：Eun Lee、Tae Seop Kang、Beom Jun Joo、Jin Sung Tae、Kap Sok Li、Cheol Keun Chung

  DOI：10.1016/0040-4039(94)02223-x

  日期：1995.1

  (Pyrrolidine)- and (piperidine)acetates are efficiently synthesized via radical cyclication of beta-aminoacrylates.
• An Access to Aza-Freidinger Lactams and <i>E</i>-Locked Analogs
  作者：Philipp A. Ottersbach、Janina Schmitz、Gregor Schnakenburg、Michael Gütschow

  DOI：10.1021/ol3030583

  日期：2013.2.1

  Freidinger lactams, possessing a peptide bond configuration locked to 4 are important key elements of conformationally restricted peptidomimetics. In the present work, the C alpha Hi+1 unit has been replaced by N, leading to novel aza-Freidinger lactams. A synthesis to corresponding building blocks and their E-locked analogs is introduced. The versatile buildings blocks reported here are expected to serve as useful elements in peptide synthesis.