(3RS,5S)-5-methyl-3-phenylsulfenyl-3-(dodec-11-ynyl)-tetrahydrofuran-2-one | 1161847-70-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3RS,5S)-5-methyl-3-phenylsulfenyl-3-(dodec-11-ynyl)-tetrahydrofuran-2-one
• 英文别名: (5S)-3-dodec-11-ynyl-5-methyl-3-phenylsulfanyloxolan-2-one
• CAS: 1161847-70-6
• 化学式: C₂₃H₃₂O₂S
• 分子量: 372.572
• InChiKey: HCINRWCUSGNYDS-AJZOCDQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5R)-2-(1’R,2’-isopropylidenedioxyethyl)-5-formyltetrahydrofuran 、 (3RS,5S)-5-methyl-3-phenylsulfenyl-3-(dodec-11-ynyl)-tetrahydrofuran-2-one 在 N-甲基麻黄碱 、 zinc trifluoromethanesulfonate 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 5.25h， 以74%的产率得到(3RS,5S)-3-{(13R)-13-hydroxy-13-[(2R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]tetrahydrofuran-2-yl]tridec-11-ynyl}-5-methyl-3-(phenylsulfenyl)tetrahydrofuran-2-one
  参考文献：
  名称：

  Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution

  摘要：

  The convergent synthesis of fluorescence-labeled solamin, an antitumor Annonaceous acetogenin, was accomplished by two asymmetric alkynylations of 2,5-diformyl tetrahydrofuran with an alkyne tagged with fluorescent groups and another alkyne with an alpha,beta-unsaturated gamma-lactone. Assay for the growth inhibitory activity against human cancer cell lines revealed that the probe with the fluorescent groups at the end of the hydrocarbon chain may have the same mode of action as natural acetogenins. The merged fluorescence of dansyl-labeled solamin and MitoTracker Red suggests that Annonaceous acetogenins localize in the mitochondria. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.004
• 作为产物：
  描述：

  12‐iodododec‐1‐yne 、 (5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 以97%的产率得到(3RS,5S)-5-methyl-3-phenylsulfenyl-3-(dodec-11-ynyl)-tetrahydrofuran-2-one
  参考文献：
  名称：

  Convergent Synthesis of Fluorescence Labeled Solamin

  摘要：

  The convergent synthesis of dansyl-labeled solamin, an antitumor Annonaceous acetogenin, has been achieved. The carbon skeleton was assembled from three fragments: the THF ring fragment, the fluorescent fragment, and the gamma-lactone fragment, by asymmetric alkynylation.

  DOI：

  10.3987/com-08-s(d)45

文献信息

• Convergent Synthesis of Fluorescence Labeled Solamin
  作者：Tetsuaki Tanaka、Naoto Kojima、Takekuni Morioka、Masahiro Yano、Yuki Suga、Naoyoshi Maezaki

  DOI：10.3987/com-08-s(d)45

  日期：——

  The convergent synthesis of dansyl-labeled solamin, an antitumor Annonaceous acetogenin, has been achieved. The carbon skeleton was assembled from three fragments: the THF ring fragment, the fluorescent fragment, and the gamma-lactone fragment, by asymmetric alkynylation.
• Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution
  作者：Naoto Kojima、Takekuni Morioka、Daisuke Urabe、Masahiro Yano、Yuki Suga、Naoyoshi Maezaki、Ayako Ohashi-Kobayashi、Yasuyuki Fujimoto、Masatomo Maeda、Takao Yamori、Takehiko Yoshimitsu、Tetsuaki Tanaka

  DOI：10.1016/j.bmc.2010.10.004

  日期：2010.12

  The convergent synthesis of fluorescence-labeled solamin, an antitumor Annonaceous acetogenin, was accomplished by two asymmetric alkynylations of 2,5-diformyl tetrahydrofuran with an alkyne tagged with fluorescent groups and another alkyne with an alpha,beta-unsaturated gamma-lactone. Assay for the growth inhibitory activity against human cancer cell lines revealed that the probe with the fluorescent groups at the end of the hydrocarbon chain may have the same mode of action as natural acetogenins. The merged fluorescence of dansyl-labeled solamin and MitoTracker Red suggests that Annonaceous acetogenins localize in the mitochondria. (C) 2010 Elsevier Ltd. All rights reserved.