benzyl (2R,3S)-2-[(1R)-1-benzoyloxyethyl]-4-methylidene-5-oxo-3-phenylpyrrolidine-2-carboxylate | 1336986-95-8

• 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: benzyl (2R,3S)-2-[(1R)-1-benzoyloxyethyl]-4-methylidene-5-oxo-3-phenylpyrrolidine-2-carboxylate
• CAS: 1336986-95-8
• 化学式: C₂₈H₂₅NO₅
• 分子量: 455.51
• InChiKey: SQVQNDVAOBADLH-GDRRSRKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲亚胺酸甲酯盐酸盐 在 盐酸 、 水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 、 乙基苯 为溶剂， 反应 8.0h， 生成 benzyl (2R,3S)-2-[(1R)-1-benzoyloxyethyl]-4-methylidene-5-oxo-3-phenylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  Stereoselective synthesis of functionalized pyroglutamates

  摘要：

  Novel stereoselective synthesis of alpha-methylene-beta-substituted pyroglutamates, and alpha-alkylidene-pyroglutamates has been achieved via substrate controlled asymmetric alkylation of L-threonine derived oxazole with Baylis-Hillman reaction based allyl bromides and acetates, respectively. The synthesized compounds were evaluated for their proteasome inhibition and cytotoxicity on multiple myeloma cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.029

文献信息

• Stereoselective synthesis of functionalized pyroglutamates
  作者：Matthew J. Just、Srinivas Tekkam、Mohammad A. Alam、Subash C. Jonnalagadda、Joseph L. Johnson、Venkatram R. Mereddy

  DOI：10.1016/j.tetlet.2011.08.029

  日期：2011.10

  Novel stereoselective synthesis of alpha-methylene-beta-substituted pyroglutamates, and alpha-alkylidene-pyroglutamates has been achieved via substrate controlled asymmetric alkylation of L-threonine derived oxazole with Baylis-Hillman reaction based allyl bromides and acetates, respectively. The synthesized compounds were evaluated for their proteasome inhibition and cytotoxicity on multiple myeloma cells. (C) 2011 Elsevier Ltd. All rights reserved.