(1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-chloroacetate | 75556-46-6

• 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: (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-chloroacetate
• 英文别名: (-)-chloroacetylborneol；[(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 2-chloroacetate
• CAS: 75556-46-6
• 化学式: C₁₂H₁₉ClO₂
• 分子量: 230.735
• InChiKey: VSQKDAUZKNYBHR-YGOYTEALSA-N

物化性质

• 沸点：
  267.2±13.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-chloroacetate 在 六氟磷酸钾 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 生成 1-[(-)-borneoxycarbonylmethyl]-3-methyl benzimidazolium hexafluorophosphate
  参考文献：
  名称：

  New benzimidazolium-based chiral ionic liquids: synthesis and application in enantioselective sodium borohydride reductions in water

  摘要：

  New chiral ionic liquids based on benzimidazolium salts have been synthesized from the reaction of (-)-menthol or (-)-borneol, chloroacetic acid and 1-methylbenzimidazole. The structures of these chiral ionic liquids have been confirmed from H-1, C-13 NMR and mass spectral studies. The application of these chiral ionic liquids in enantioselective sodium borohydride reductions of prochiral ketones to produce optically active alcohols has been studied. The effect of the solvent on the enantioselectivity and reusability of the chiral catalyst has also been studied. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.04.004
• 作为产物：
  描述：

  左旋樟脑 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-chloroacetate
  参考文献：
  名称：

  Monoterpenoid-based inhibitors of filoviruses targeting the glycoprotein-mediated entry process

  摘要：

  In this study, we screened a large library of (+)-camphor and (-)-borneol derivatives to assess their filovirus entry inhibition activities using pseudotype systems. Structure-activity relationship studies revealed several compounds exhibiting submicromolar IC₅₀ values. These compounds were evaluated for their effect against natural Ebola virus (EBOV) and Marburg virus. Compound 3b (As-358) exhibited the good antiviral potency (IC₅₀ = 3.7 μM, SI = 118) against Marburg virus, while the hydrochloride salt of this compound 3b·HCl had a strong inhibitory effect against Ebola virus (IC₅₀ = 9.1 μM, SI = 31) and good in vivo safety (LD₅₀ > 1000 mg/kg). The results of molecular docking and in vitro mutagenesis analyses suggest that the synthesized compounds bind to the active binding site of EBOV glycoprotein similar to the known inhibitor toremifene.

  DOI：

  10.1016/j.ejmech.2020.112726

文献信息

• Synthesis of new chiral ionic liquids based on (−)-menthol and (−)-borneol
  作者：Ricardo Alexandre F. Matos、Carlos Kleber Z. Andrade

  DOI：10.1016/j.tetlet.2008.01.011

  日期：2008.3

  New chiral ionic liquids (CILs) based on (−)-menthol and (−)-borneol were designed and synthesized in very good yields using a simple and efficient 3-step strategy. The properties and characterization of these compounds are discussed.

  使用简单有效的三步策略，以很高的收率设计和合成了基于（-）-薄荷醇和（-）-冰片的新型手性离子液体（CIL）。讨论了这些化合物的性质和表征。
• Synthesis and in vitro study of novel borneol derivatives as potent inhibitors of the influenza A virus
  作者：A. S. Sokolova、O. I. Yarovaya、M. D. Semenova、A. A. Shtro、I. R. Orshanskaya、V. V. Zarubaev、N. F. Salakhutdinov

  DOI：10.1039/c6md00657d

  日期：——

  Herein, we present the design and synthesis of a series of novel heterocyclic derivatives of (−)-borneol and (−)-isoborneol as potent inhibitors of the influenza A virus. All compounds were tested for their toxicity against MDCK cells and for virus-inhibiting activity against the influenza virus A/Puerto Rico/8/34 (H1N1). Compounds 7, 16 and 26 containing a morpholine fragment exhibited the highest

  在本文中，我们介绍了设计和合成一系列新型（-）-冰片和（-）-异冰片的杂环衍生物，作为A型流感病毒的有效抑制剂。测试了所有化合物对MDCK细胞的毒性以及对流感病毒A / Puerto Rico / 8/34（H1N1）的病毒抑制活性。化合物7，16和26含有一个吗啉片段表现出最高效率剂抑制流感病毒A（H1N1）为82，45和65，相应的选择性的指标的复制。导数9（SI = 23）和18含有1-甲基哌嗪基序的（SI = 25）显示中等的抗病毒活性。对这一系列新的冰片衍生物的结构活性分析表明，抗病毒活性需要1,7,7-三甲基双环[2.2.1]庚烷骨架。
• Reactions of<i>t</i>-Butylphosphine–Borane with Various Electrophiles and Synthesis of Optically Active<i>t</i>-Butylmethylphosphine–Borane
  作者：Nobuhiko Oohara、Tsuneo Imamoto

  DOI：10.1246/bcsj.75.1359

  日期：2002.6

  The reactivity of t-butylphosphine–borane toward various electrophiles was studied with a focus on alkylation. Monoalkylation of this compound proceeded smoothly in good yields (61–85%). Disubstituted derivatives were also synthesized in good yields (86–99%). Optically active t-butylmethylphosphine–borane was prepared from t-butylphosphine–borane by resolution of intermediate diastereomers of (1S)-endo-2-bornyloxycarbonyl(t-butyl)methylphosphine-borane.

  对t-丁基磷烷-硼烷与各种电亲核试剂的反应性进行了研究，重点关注烷基化。这种化合物的单烷基化过程顺利进行，产率良好（61-85%）。还合成了二取代衍生物，产率也很好（86-99%）。通过分离中间反式异构体(1S)-内源-2-硼酸酯(t-丁基)甲基磷烷-硼烷，制备了光学活性的t-丁基甲基磷烷-硼烷。
• Synthesis and biological activity of heterocyclic borneol derivatives
  作者：Anastasiya S. Sokolova、Olga I. Yarovaya、Anna A. Shtro、Marina S. Borisova、Ekaterina A. Morozova、Tatyana G. Tolstikova、Vladimir V. Zarubaev、Nariman F. Salakhutdinov

  DOI：10.1007/s10593-017-2063-3

  日期：2017.3

  A series of novel heterocyclic derivatives of (–)-borneol has been prepared by the interaction of (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]-heptan-2-yl 2-chloroacetate and (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 3-chloropropanoate with different N- and S-nucleophiles. The obtained products were screened for antiviral, antiulcer, and analgesic activity.

  通过（1 S，2 R，4 S）-1,7,7-三甲基双环[2.2.1]-庚-2-基2-的相互作用制备了一系列新的（-）-冰片杂环衍生物氯乙酸盐和（1 S，2 R，4 S）-1,7,7-三甲基双环[2.2.1]庚-2-基3-氯丙酸酯与不同的N-和S-亲核试剂。筛选获得的产品的抗病毒，抗溃疡和止痛活性。
• Discovery of a New Class of Inhibitors of Vaccinia Virus Based on (−)-Borneol from <i>Abies sibirica</i> and (+)-Camphor
  作者：Anastasiya S. Sokolova、Olga I. Yarovaya、Nikolay I. Bormotov、Larisa N. Shishkina、Nariman F. Salakhutdinov

  DOI：10.1002/cbdv.201800153

  日期：2018.9

  A series of the bornyl ester/amide derivatives with N-containing heterocycles were designed and synthesized as vaccinia virus (VV) inhibitors. Bioassay results showed that among the designed compounds, derivatives 6, 13, 14, 34, 36 and 37 showed the best inhibitory activity against VV with the IC50 values of 12.9, 17.9, 3.4, 2.5, 12.5 and 7.5 μm, respectively, and good cytotoxicity. The primary structure-activity

  设计并合成了一系列带有含N杂环的冰片酯/酰胺衍生物，作为痘苗病毒（VV）抑制剂。生物测定结果表明，在设计的化合物中，衍生物6、13、14、34、36和37对VV的抑制作用最佳，IC50值分别为12.9、17.9、3.4、2.5、12.5和7.5μm，效果良好。细胞毒性。初步的结构-活性关系（SAR）研究表明，饱和的N-杂环（例如吗啉或4-甲基哌啶）与1,7,7-三甲基双环[2.2.1]庚烷骨架的组合有利于抗病毒活性。