syn-N-(t-butoxycarbonyl)-5-carboxy-2-azabicyclo[2.1.1]hexane | 1256914-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: syn-N-(t-butoxycarbonyl)-5-carboxy-2-azabicyclo[2.1.1]hexane
• 英文别名: (1R*,4S*,5S*)-2-tert-butoxycarbonyl-2-azabicyclo[2.1.1]hexane-5-carboxylic acid；(-/+)-(1S,4R,5R)-5-syn-carboxylic-N-Boc-2-azabicyclo[2.1.1]-hexane；(1S,4R,5R)-2-tert-butoxycarbonyl-2-azabicyclo[2.1.1]hexane-5-carboxylic acid；(1S,4R,5R)-2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[2.1.1]hexane-5-carboxylic acid
• CAS: 1256914-30-3；615575-74-1
• 化学式: C₁₁H₁₇NO₄
• 分子量: 227.26
• InChiKey: VGONMHFNYUTBCO-BIIVOSGPSA-N

物化性质

• 沸点：
  355.9±25.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  syn-N-(t-butoxycarbonyl)-5-carboxy-2-azabicyclo[2.1.1]hexane 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 tert-butyl 2-azabicyclo[2.1.1]hexane-2-carboxylate
  参考文献：
  名称：

  Krow, Grant R.; Lin, Guoliang; Herzon, Seth B., Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7562 - 7564

  摘要：

  DOI：
• 作为产物：
  描述：

  syn-N-(t-butoxycarbonyl)-5-acetyl-2-azabicyclo[2.1.1]hexane 在 sodium hypochlorite 作用下， 生成 syn-N-(t-butoxycarbonyl)-5-carboxy-2-azabicyclo[2.1.1]hexane
  参考文献：
  名称：

  5-Carboxy-2-azabicyclo[2.1.1]hexanes as Precursors of 5-Halo, Amino, Phenyl, and 2-Methoxycarbonylethyl Methanopyrrolidines

  摘要：

  [GRAPHICS]Novel 5-X-substituted-2-azabicyclo[2.1.1]hexanes (X = 5-syn-Cl, -Br, -I, -Ph, -NHCOOR (R = Me, Bn, t-Bu), -CH2CH2COOMe and X = 5-anti-Br, -I, -Ph) were synthesized from the X = 5-syn-carboxy derivative. New 5-anti-X-2-azabicyclo[2.1.1]hexanes, X = NECOOR (R = Me, Bn), were prepared stereoselectively from the X = 5-anti-carboxy substrate.

  DOI：

  10.1021/jo052506b

文献信息

• Transfer of photochemistry from UV to visible: An expedient access to a bridged pyrrolidine
  作者：Olivier Lorthioir、Thomas Corner、Sylvain Demanze、Ryan Greenwood、Katie Proctor、Stephen Stokes、Paul Turner

  DOI：10.1016/j.tetlet.2021.153447

  日期：2021.11

  In this study we successfully transferred a useful photochemical reaction from the UV to the visible region of the spectrum. Use of a commercially available iridium complex facilitated triplet state intramolecular [2 + 2] photocycloaddition under irradiation with the now readily available, compact and convenient blue light sources, therefore avoiding the need for direct UV irradiation. Under these

  在这项研究中，我们成功地将有用的光化学反应从紫外线转移到光谱的可见光区域。使用市售的铱配合物促进了三重态分子内 [2 + 2] 光环加成，在现在容易获得的、紧凑和方便的蓝色光源的照射下，因此避免了直接紫外线照射的需要。在这些温和的条件下，我们能够在标准的研究实验室通风橱中高效生产克数量的医学相关但未充分利用的桥连吡咯烷。
• Krow, Grant R.; Lin, Guoliang; Herzon, Seth B., Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7562 - 7564
  作者：Krow, Grant R.、Lin, Guoliang、Herzon, Seth B.、Thomas, Andrew M.、Moore, Keith P.、Huang, Qiuli、Carroll, Patrick J.

  DOI：——

  日期：——
• Oligomers of a 5-Carboxy-methanopyrrolidine β-Amino Acid. A Search for Order
  作者：Grant R. Krow、Nian Liu、Matthew Sender、Guoliang Lin、Ryan Centafont、Philip E. Sonnet、Charles DeBrosse、Charles W. Ross、Patrick J. Carroll、Matthew D. Shoulders、Ronald T. Raines

  DOI：10.1021/ol1022917

  日期：2010.12.3

  CD spectra for homooligomers (n = 4, 6, 8) of (1S,4R,5R)-5-syn-carboxy-2-azabicyclo[2.1.1]hexane (MPCA), a methano-bridged pyrrolidine beta-carboxylic acid, suggest an ordered secondary structure. Even in the absence of internal hydrogen bonding, solution NMR, X-ray, and in silico analyses of the tetramer are indicative of conformations with trans-amides and C-5-amide-carbonyls oriented toward the C-4 bridgehead This highly constrained beta-amino acid could prove useful in the ongoing development of well-defined foldamers.
• 5-Carboxy-2-azabicyclo[2.1.1]hexanes as Precursors of 5-Halo, Amino, Phenyl, and 2-Methoxycarbonylethyl Methanopyrrolidines
  作者：Grant R. Krow、Qiuli Huang、Guoliang Lin、Ryan A. Centafont、Andrew M. Thomas、Deepa Gandla、Charles DeBrosse、Patrick J. Carroll

  DOI：10.1021/jo052506b

  日期：2006.3.1

  [GRAPHICS]Novel 5-X-substituted-2-azabicyclo[2.1.1]hexanes (X = 5-syn-Cl, -Br, -I, -Ph, -NHCOOR (R = Me, Bn, t-Bu), -CH2CH2COOMe and X = 5-anti-Br, -I, -Ph) were synthesized from the X = 5-syn-carboxy derivative. New 5-anti-X-2-azabicyclo[2.1.1]hexanes, X = NECOOR (R = Me, Bn), were prepared stereoselectively from the X = 5-anti-carboxy substrate.