10-hydroxyisopinocampheylthiol | 444308-38-7

• 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: 10-hydroxyisopinocampheylthiol
• 英文别名: {(1s,2r,3s,5r)-3-Mercapto-6,6-dimethylbicyclo[3.1.1]heptan-2-yl}methanol；[(1S,2R,3S,5R)-6,6-dimethyl-3-sulfanyl-2-bicyclo[3.1.1]heptanyl]methanol
• CAS: 444308-38-7
• 化学式: C₁₀H₁₈OS
• 分子量: 186.318
• InChiKey: ALTHCULBPWEXMZ-XGEHTFHBSA-N

物化性质

• 沸点：
  270.5±13.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-hydroxyisopinocampheylthiol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 (1S,2R,8R,9S,13S,17S)-4,6-dioxa-14,16-dithia-5-acetyl-10,10,20,20-tetramethypentacyclo-[17.4.1.1.1^9,11.0^2,17.0^8,13]-docosane
  参考文献：
  名称：

  Synthesis of acyldodecaheterocycles derived from (1R)-(–)-myrtenal and evaluation as chiral auxiliaries

  摘要：

  New (1R)-(-)-myrtenal-derived macrocycles 5a and 5b were efficiently used as chiral auxiliaries in the diastereoselective nucleophilic addition of several nucleophiles (RMgX, RLi, LiAlH4, and NaBH4). We observed that the diastereoselectivity depended on the nucleophile, with the stereoselectivity order being RMgX (>99:1 dr) > RLi (7:3 dr) > AlLiH4 >= NaBH4 (6:4 dr). The absolute configuration of the resulting carbinols was established by X-ray diffraction of adducts 9a and 9b, and through chemical correlation of carbinols 9b and 9c with diols of known absolute configuration. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.013
• 作为产物：
  描述：

  (1S,2R,3S)-2-formyl-6,6-dimethyl-3-acetylthiobicyclo[3.1.1]heptane 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 10-hydroxyisopinocampheylthiol
  参考文献：
  名称：

  Synthesis of acyldodecaheterocycles derived from (1R)-(–)-myrtenal and evaluation as chiral auxiliaries

  摘要：

  New (1R)-(-)-myrtenal-derived macrocycles 5a and 5b were efficiently used as chiral auxiliaries in the diastereoselective nucleophilic addition of several nucleophiles (RMgX, RLi, LiAlH4, and NaBH4). We observed that the diastereoselectivity depended on the nucleophile, with the stereoselectivity order being RMgX (>99:1 dr) > RLi (7:3 dr) > AlLiH4 >= NaBH4 (6:4 dr). The absolute configuration of the resulting carbinols was established by X-ray diffraction of adducts 9a and 9b, and through chemical correlation of carbinols 9b and 9c with diols of known absolute configuration. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.013

文献信息

• Synthesis of a New (1<i>R</i>)-(−)-Myrtenal-Derived Dioxadithiadodecacycle and Its Use as an Efficient Chiral Auxiliary
  作者：M. Elena Vargas-Díaz、Pedro Joseph-Nathan、Joaquín Tamariz、L. Gerardo Zepeda

  DOI：10.1021/ol062319f

  日期：2007.1.1

  [reaction: see text] The new macrocycle 9 (>70% yield from hydroxythiol 10) was treated with several nucleophilic reagents (RMgX, RLi, and LiAlH4) affording carbinols 12a-j (80-96% yield, >99:1 dr). Oxidative hydrolysis of 12a,c,e, followed by LiAlH4 reduction of the resulting mixture, gave 16a,c,e in >95% ee,16c being a key precursor for the preparation of fungicide 17. The absolute configuration

  [反应：请参见文本]用几种亲核试剂（RMgX，RLi和LiAlH4）处理了新的大环化合物9（羟基硫醇10的产率> 70％），得到甲醇12a-j（产率80-96％，> 99：1 dr ）。12a，c，e的氧化水解，然后将所得混合物进行LiAlH4还原，得到> 95％ee，16c的16a，c，e，这是制备杀菌剂17的关键前体。9和12j的绝对构型（ Nu = H）是通过单晶X射线衍射分析和化学相关性建立的。
• New S-Monoterpenylcysteines
  作者：A. K. Melekhin、D. V. Sudarikov、O. G. Shevchenko、S. A. Rubtsova、A. V. Kuchin

  DOI：10.1007/s10600-018-2324-0

  日期：2018.3

  New sulfides based on 4-caranethiol, 3-hydroxyisocaranethiol, neomenthanethiol, 10-thioisoborneol, 10-hydroxyisocamphenylthiol, and 10-thioisocampheol containing L-serine residues were synthesized for the first time in 40–70% yields. The synthesized compounds were not cytotoxic in a laboratory mouse erythrocyte hemolysis model and possessed statistically significant membrane-protective and antioxidant activity at a concentration of 50 μmol/L.

  首次合成了基于4-香菜硫醇、3-羟基异香菜硫醇、新薄荷硫醇、10-硫代异龙脑、10-羟基异莰苯硫醇和含有L-丝氨酸残基的10-硫代异莰酚的新型硫化物，产率40-70%。合成的化合物在实验室小鼠红细胞溶血模型中不具有细胞毒性，并且在浓度为 50 μmol/L 时具有统计学显着的膜保护和抗氧化活性。
• Synthesis and Antioxidant Activity of Carane and Pinane Based Sulfenimines and Sulfinimines
  作者：Denis V. Sudarikov、Yulia V. Krymskaya、Oksana G. Shevchenko、Pavel A. Slepukhin、Svetlana A. Rubtsova、Aleksandr V. Kutchin

  DOI：10.1002/cbdv.201900413

  日期：2019.11

  The synthesis of sulfenimines and sulfinimines has been carried out with 10‐hydroxyisocamphylthiol. The configuration of the compounds has been deduced by methods of NMR, DFT calculations and X‐ray diffraction analysis. The cytotoxic, antioxidant and membrane‐protective activity of the synthesized compounds as well as of the previously obtained sulfenimines and sulfinimines based on 4‐caranethiol have

  亚磺亚胺和亚磺亚胺的合成是用 10-羟基异樟脑硫醇进行的。化合物的构型已经通过NMR、DFT计算和X射线衍射分析的方法推导出来。已经确定了合成化合物以及先前获得的基于 4-caranethiol 的亚磺亚胺和亚磺亚胺的细胞毒性、抗氧化和膜保护活性。
• Synthesis and antioxidant activity of monoterpene nitrobenzylidenesulfenimines
  作者：Denis V. Sudarikov、Yulia V. Krymskaya、Anatoliy K. Melekhin、Oksana G. Shevchenko、Svetlana A. Rubtsova

  DOI：10.1007/s11696-020-01362-4

  日期：2021.6

  Novel nitrobenzylidenesulfenimines based on monoterpene hydroxythiols were synthesized with yields of 51–84% for the first time. The obtained compounds showed high antioxidant and membrane-protective activities in in vitro models.

  首次合成了基于单萜羟基硫醇的新型硝基亚苄基亚磺胺，产率为 51-84%。所得化合物在体外模型中显示出高抗氧化和膜保护活性。
• Synthesis and Biological Activity of Unsymmetrical Monoterpenylhetaryl Disulfides
  作者：Denis V. Sudarikov、Yulia V. Gyrdymova、Alexander V. Borisov、Julia M. Lukiyanova、Roman V. Rumyantcev、Oksana G. Shevchenko、Diana R. Baidamshina、Nargiza D. Zakarova、Airat R. Kayumov、Ekaterina O. Sinegubova、Alexandrina S. Volobueva、Vladimir V. Zarubaev、Svetlana A. Rubtsova

  DOI：10.3390/molecules27165101

  日期：——

  New unsymmetrical monoterpenylhetaryl disulfides based on heterocyclic disulfides and monoterpene thiols were synthesized for the first time in 48–88% yields. Hydrolysis of disulfides with fragments of methyl esters of 2-mercaptonicotinic acid was carried out in 73–95% yields. The obtained compounds were evaluated for antioxidant, antibacterial, antifungal activity, cytotoxicity and mutagenicity.

  首次以 48-88% 的产率合成了基于杂环二硫化物和单萜硫醇的新型不对称单萜基杂芳基二硫化物。二硫化物与 2-巯基烟酸甲酯片段的水解以 73-95% 的产率进行。评价所得化合物的抗氧化、抗菌、抗真菌活性、细胞毒性和致突变性。