β-cryptoxanthin pentynoate | 1374137-42-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: β-cryptoxanthin pentynoate
• 英文别名: [(1R)-3,5,5-trimethyl-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-3-en-1-yl] pent-4-ynoate
• CAS: 1374137-42-4
• 化学式: C₄₅H₆₀O₂
• 分子量: 632.97
• InChiKey: BKNPYZUFDNCWOI-GWIXBFACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  D-glucopyranosyl azide 、 β-cryptoxanthin pentynoate 在 bis-triphenylphosphano-copper(I) butyrate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以76%的产率得到3-(1-(β-D-glucopyranosyl)-1,2,3-triazol-4-yl)propanoyloxy-β,β-carotene
  参考文献：
  名称：

  Synthesis of carotenoid-monosaccharide conjugates via azide–alkyne click-reaction

  摘要：

  Carotenoid pentynoates were coupled to protected and unprotected sugar azides via an azide-alkyne click-reaction using bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)(2)) complex. Protected sugars delivered the conjugates with excellent yields, whereas with unprotected ones amphipathic carotenoid-sugar derivatives were obtained in good or moderate yields in a simple way. (C )2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.12.035
• 作为产物：
  描述：

  炔丙基脲 、 隐黄质 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以90%的产率得到β-cryptoxanthin pentynoate
  参考文献：
  名称：

  Synthesis of carotenoid-monosaccharide conjugates via azide–alkyne click-reaction

  摘要：

  Carotenoid pentynoates were coupled to protected and unprotected sugar azides via an azide-alkyne click-reaction using bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)(2)) complex. Protected sugars delivered the conjugates with excellent yields, whereas with unprotected ones amphipathic carotenoid-sugar derivatives were obtained in good or moderate yields in a simple way. (C )2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.12.035

文献信息

• Introduction of click chemistry to carotenoids
  作者：Magdolna Háda、Veronika Nagy、Anikó Takátsy、József Deli、Jan Hait、Attila Agócs

  DOI：10.1016/j.tetlet.2012.03.027

  日期：2012.5

  We describe the synthesis of carotenoid derivatives via the azide-alkyne click reaction and optimize the conditions for these sensitive molecules. After finding the mildest conditions possible for the reaction we were able to use the click reaction for the synthesis of PEG-carotenoid conjugates starting from carotenoid pentynoates and PEG azides. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of carotenoid-monosaccharide conjugates via azide–alkyne click-reaction
  作者：Attila Agócs、Éva Bokor、Anikó Takátsy、Tamás Lóránd、József Deli、László Somsák、Veronika Nagy

  DOI：10.1016/j.tet.2016.12.035

  日期：2017.2

  Carotenoid pentynoates were coupled to protected and unprotected sugar azides via an azide-alkyne click-reaction using bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)(2)) complex. Protected sugars delivered the conjugates with excellent yields, whereas with unprotected ones amphipathic carotenoid-sugar derivatives were obtained in good or moderate yields in a simple way. (C )2016 Elsevier Ltd. All rights reserved.