2-(((1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)sulfanyl)ethanol

• 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: 2-(((1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)sulfanyl)ethanol
• 英文别名: 2-(((1s,2s,4s)-1,7,7-Trimeth-ylbicyclo[2.2.1]hept-2-yl)thio)ethanol；2-[[(1S,2S,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]sulfanyl]ethanol
• 化学式: C₁₂H₂₂OS
• 分子量: 214.372
• InChiKey: AGZBMLIJEPVRHP-JBLDHEPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(((1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)sulfanyl)ethanol 在 吡啶 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 以80%的产率得到(2-chloroethyl)-((1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)sulfide
  参考文献：
  名称：

  Synthesis and membrane protective activity of bis-sulfides derived from monoterpenoids and monosaccharides

  摘要：

  Hydroxyl- and chloroethyl derivatives of neomenthane- and isobornanethiol in yields of to 80% were synthesized. They served as the basis for the preparation of new bis-sulfides with diacetone-protected galacto- and fructopyranose fragments in yields up to 98%. The bis-sulfides synthesized were screened for membrane protective and antioxidant properties in a model cell system (in vitro) based on their ability to inhibit the H2O2-induced hemolysis of erythrocytes and retard the oxyhemoglobin oxidation.

  DOI：

  10.1134/s1068162017030141
• 作为产物：
  描述：

  (+)-冰片 在 吡啶 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(((1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)sulfanyl)ethanol
  参考文献：
  名称：

  Synthesis and membrane protective activity of bis-sulfides derived from monoterpenoids and monosaccharides

  摘要：

  Hydroxyl- and chloroethyl derivatives of neomenthane- and isobornanethiol in yields of to 80% were synthesized. They served as the basis for the preparation of new bis-sulfides with diacetone-protected galacto- and fructopyranose fragments in yields up to 98%. The bis-sulfides synthesized were screened for membrane protective and antioxidant properties in a model cell system (in vitro) based on their ability to inhibit the H2O2-induced hemolysis of erythrocytes and retard the oxyhemoglobin oxidation.

  DOI：

  10.1134/s1068162017030141

文献信息

• Isobornanyl sulfoxides and isobornanyl sulfone: Physicochemical characteristics and the features of crystal structure
  作者：Olga A. Lodochnikova、Daut R. Islamov、Daria P. Gerasimova、Dmitry V. Zakharychev、Alina F. Saifina、Svetlana V. Pestova、Evgeny S. Izmest'ev、Svetlana A. Rubtsova、Roman S. Pavelyev、Ilfat Z. Rakhmatullin、Vladimir V. Klochkov、Olga V. Ostolopovskaya、Liliya E. Nikitina、Patrick Rollin

  DOI：10.1016/j.molstruc.2021.130491

  日期：2021.9

  crystals of diastereomeric sulfoxides. The isobornanyl sulfone crystal is formed in a complex way – two crystallographically independent molecules playing different roles in the formation of H-bonds. The IR spectra of a diastereomeric sulfoxides mixture demonstrate the averaging of the synthon-forming functional groups bands. In a counterbalance, the IR spectrum of isobornanyl sulfone shows a doubling of

  介绍了新合成的异冰片烷基亚砜和砜的理化特性和晶体结构。纯化后，以2：1的低共熔比率获得非对映亚砜，其不允许分离或富集混合物。根据热化学数据，重建了系统的相图形式，表明非对映异构体具有明显不同的熔点。根据X射线数据，非对映亚砜的晶体中建立了相同的超分子开链S = O·⋅⋅H-O合成子。异冰片基砜晶体的形成过程很复杂-两个在晶体学上独立的分子在氢键的形成中起着不同的作用。非对映异构亚砜混合物的红外光谱显示形成合成子的官能团带的平均数。在平衡中，异冰片基砜的红外光谱显示属于同手性均相但结晶学上不等价的合成子形成官能团的关键带加倍。
• Conjugate of meso-carboxysubstituted-BODIPY with thioterpenoid as an effective fluorescent probe: Synthesis, structure, spectral characteristics, and molecular docking
  作者：Galina B. Guseva、Elena V. Antina、Mikhail B. Berezin、Alexander A. Ksenofontov、Pavel S. Bocharov、Anastassia S. Smirnova、Roman S. Pavelyev、Ilmir R. Gilfanov、Svetlana V. Pestova、Evgeny S. Izmest'ev、Svetlana A. Rubtsova、Airat R. Kayumov、Sergei V. Kiselev、Zulfiya R. Azizova、Olga V. Ostolopovskaya、Sergey V. Efimov、Vladimir V. Klochkov、Ilya A. Khodov、Liliya E. Nikitina

  DOI：10.1016/j.saa.2021.120638

  日期：2022.3

  thioterpene fragment was carried out in order to find out the antiplatelet and anticoagulant action mechanisms of thioterpenoids and to assess the membrane and receptor factors contributions. The molecular structure of the conjugate was confirmed via UV/vis-, NMR- and MS-spectra. It is found that the probe is a high fluorescence quantum yield (to ∼100%) in the blue-green region at 509–516 nm. Molecular docking

  本文致力于设计一种基于具有硫萜片段的内消旋羧基取代的 BODIPY的荧光探针。进行了硫萜片段上 BODIPY 分子中甲氧基的功能替换，以找出硫萜类化合物的抗血小板和抗凝作用机制，并评估膜和受体因子的贡献。通过UV/vis-、NMR-和MS-光谱证实了缀合物的分子结构。发现该探针在 509-516 nm 的蓝绿色区域具有高荧光量子产率（约 100%）。所有研究分子的分子对接表明，与萜类化合物结合的 BODIPY 是增加其对血小板受体 P2Y 12亲和力的极好方法。
• Nikitina, L. E.; Shkuro, O. A.; Plemenkov, V. V., Russian Journal of Organic Chemistry, 1993, vol. 29, # 9.1, p. 1491 - 1494
  作者：Nikitina, L. E.、Shkuro, O. A.、Plemenkov, V. V.

  DOI：——

  日期：——
• Synthesis and membrane protective activity of bis-sulfides derived from monoterpenoids and monosaccharides
  作者：S. V. Pestova、E. S. Izmest’ev、O. G. Shevchenko、S. A. Rubtsova、A. V. Kuchin

  DOI：10.1134/s1068162017030141

  日期：2017.5

  Hydroxyl- and chloroethyl derivatives of neomenthane- and isobornanethiol in yields of to 80% were synthesized. They served as the basis for the preparation of new bis-sulfides with diacetone-protected galacto- and fructopyranose fragments in yields up to 98%. The bis-sulfides synthesized were screened for membrane protective and antioxidant properties in a model cell system (in vitro) based on their ability to inhibit the H2O2-induced hemolysis of erythrocytes and retard the oxyhemoglobin oxidation.