(2R,5R)-2-(1’R,2’-isopropylidenedioxyethyl)-5-formyltetrahydrofuran | 1161847-69-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,5R)-2-(1’R,2’-isopropylidenedioxyethyl)-5-formyltetrahydrofuran
• 英文别名: (2R,5R)-2-formyl-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]tetrahydrofuran；(2R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]oxolane-2-carbaldehyde
• CAS: 1161847-69-3
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: XIBIPGCOTSRQRV-IWSPIJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

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：

  (2R,5R)-2-(1’R,2’-isopropylidenedioxyethyl)-5-(iodomethyl)tetrahydrofuran 在 potassium superoxide 、 草酰氯 、 18-冠醚-6 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.6h， 生成 (2R,5R)-2-(1’R,2’-isopropylidenedioxyethyl)-5-formyltetrahydrofuran
  参考文献：
  名称：

  从溴苯化学酶法合成壬基产乙酸甘油酯的反式-四氢呋喃核

  摘要：

  通过分子内的碘醚化反应已经合成了存在于产乙酸素中的两种类型的反式-THF核。分几步从溴苯的微生物氧化产生的手性顺式二醇中获得起始烯醇。环化作用使在THF手性碳原子上具有（S，S）或（R，R）构型的反式THF核具有完全的立体选择性。

  DOI：

  10.1021/ol400650v

文献信息

• Synthesis of dansyl-labeled probe of thiophene analogue of annonaceous acetogenins for visualization of cell distribution and growth inhibitory activity toward human cancer cell lines
  作者：Naoto Kojima、Yuki Suga、Takuya Matsumoto、Tetsuaki Tanaka、Akinobu Akatsuka、Takao Yamori、Shingo Dan、Hiroki Iwasaki、Masayuki Yamashita

  DOI：10.1016/j.bmc.2015.01.037

  日期：2015.3

  The convergent synthesis of the dansyl-labeled probe of the thiophene-3-carboxamide analogue of annonaceous acetogenins, which shows potent antitumor activity, was accomplished by two asymmetric alkynylations of the 2,5-diformyl THF equivalent with an alkyne having a thiophene moiety and another alkyne tagged with a dansyl group. The growth inhibitory profiles toward 39 human cancer cell lines revealed that the probe retained the biological function of its mother compound, and would be useful for studying cellular activity. (C) 2015 Elsevier Ltd. All rights reserved.
• 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.
• Chemoenzymatic Synthesis of <i>trans</i>-Tetrahydrofuran Cores of Annonaceous Acetogenins from Bromobenzene
  作者：Juan Carlos Ramos、Margarita Brovetto、Gustavo A. Seoane

  DOI：10.1021/ol400650v

  日期：2013.4.19

  Two types of trans-THF cores, present in acetogenins, have been synthesized by an intramolecular iodoetherification reaction. The starting alkenol was obtained in a few steps from a chiral cis-diol resulting from microbial oxidation of bromobenzene. The cyclization gave complete stereoselectivity for trans-THF cores with either (S,S) or (R,R) configurations at the THF chiral carbons.

  通过分子内的碘醚化反应已经合成了存在于产乙酸素中的两种类型的反式-THF核。分几步从溴苯的微生物氧化产生的手性顺式二醇中获得起始烯醇。环化作用使在THF手性碳原子上具有（S，S）或（R，R）构型的反式THF核具有完全的立体选择性。
• 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.