(1R,5S,6S)-5-(N-(tert-Butoxycarbonyl)amino)-3-oxobicyclo<4.1.0>heptan-2-one | 124151-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,5S,6S)-5-(N-(tert-Butoxycarbonyl)amino)-3-oxobicyclo<4.1.0>heptan-2-one
• 英文别名: (1R,5S,6S)-5-[N-(tert-Butoxycarbonyl)amino]-3-oxobicyclo[4.1.0]heptan-2-one；tert-butyl N-[(1R,5S,6S)-2-oxo-3-oxabicyclo[4.1.0]heptan-5-yl]carbamate
• CAS: 124151-69-5
• 化学式: C₁₁H₁₇NO₄
• 分子量: 227.26
• InChiKey: BFNWTCKRELLPFM-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  N-叔丁氧羰基-L-谷氨酸 5-甲酯 在 OAc)2 、 钯 palladium diacetate 、 sodium tetrahydroborate 、 D(+)-10-樟脑磺酸 、 N,N'-二环己基碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 乙酸乙酯 、 乙腈 、 苯 为溶剂， 反应 4.25h， 生成 (1R,5S,6S)-5-(N-(tert-Butoxycarbonyl)amino)-3-oxobicyclo<4.1.0>heptan-2-one
  参考文献：
  名称：

  Shimamoto, Keiko; Ohfune, Yasufumi, Tetrahedron Letters, 1989, vol. 30, # 29, p. 3803 - 3804

  摘要：

  DOI：

文献信息

• Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogs
  作者：Keiko Shimamoto、Michiko Ishida、Haruhikio Shinozaki、Yasufumi Ohfune

  DOI：10.1021/jo00013a018

  日期：1991.6

  To determine what conformations of L-glutamate (L-Glu) activate that compound's different receptors in the mammalian central nervous system, four diastereomeric L-2-(carboxycyclopropyl)glycines, 1-4, which are conformationally constrained analogues of the extended and folded conformers of L-Glu, were synthesized and subjected to neutrophysiological assay. Compounds 1-4 were efficiently synthesized from chiral amino acids. Cyclopropanation of the (2S)-2-amino-3-butenol derivative 5b gave intermediates for the synthesis of all four diastereomers. Stereoselective cyclopropanation of both the alpha,beta-unsaturated gamma-lactam 16 and the delta-lactone 19 gave precursors of (2S,1'S,2'R)-3 and (2S,1'R,2'S)-4, respectively. Neurophysiological assays of 1-4 performed with the newborn rat spinal cord demonstrated that the compounds induced a variety of depolarizing effects. The results of the assays strongly suggested that the N-methyl-D-aspartic acid (NMDA) receptor is activated by the folded conformer of L-Glu and that the extended conformer of L-Glu activates the metabotropic L-Glu receptor. The four analogous D-2-(carboxycyclopropyl)glycines (D-1-D-4), which were synthesized from (2R)-5b, proved to be NMDA agonists.
• SHIMAMOTO, KEIKO;ISHIDA, MICHIKO;SHINOZAKI, HARUHIKIO;OHFUNE, YASUFUMI, J. ORG. CHEM., 56,(1991) N3, C. 4167-4176
  作者：SHIMAMOTO, KEIKO、ISHIDA, MICHIKO、SHINOZAKI, HARUHIKIO、OHFUNE, YASUFUMI

  DOI：——

  日期：——