(1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-chloroacetate | 89299-71-8

• 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,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-chloroacetate
• 英文别名: [(1S,2S,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 2-chloroacetate
• CAS: 89299-71-8
• 化学式: C₁₂H₁₉ClO₂
• 分子量: 230.735
• InChiKey: VSQKDAUZKNYBHR-HOTUBEGUSA-N

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,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-chloroacetate 在 吡啶 、 苄基三乙基氯化铵 、 溶剂黄146 、 sodium nitrite 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 7.58h， 生成 (1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (E)-2-cyano-2-((((((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methyl)sulfonyl)oxy)imino)acetate
  参考文献：
  名称：

  Blanco, Jose M.; Caamano, Olga; Eirin, Ana, Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 12, p. 923 - 930

  摘要：

  DOI：
• 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 19.0h， 生成 (1S,2S,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

• Cinchona-alkaloid-based catalysts, and asymmetric alcoholysis of cyclic anhydrides using them
  申请人：Deng Li

  公开号：US20050043353A1

  公开（公告）日：2005-02-24

  One aspect of the present invention relates to cinchona-alkaloid-based catalysts. A second aspect of the invention relates to a method of preparing a derivatized cinchona alkaloid catalyst by reacting a cinchona-alkaloid with base and a compound that has a suitable leaving group. Another aspect of the present invention relates to a method of preparing a chiral, non-racemic compound from a prochiral cyclic anhydride or a meso cyclic anhydride, comprising the step of: reacting a prochiral cyclic anhydride or a meso cyclic anhydride with a nucleophile in the presence of a catalyst; wherein said prochiral cyclic anhydride or meso cyclic anhydride comprises an internal plane of symmetry or point of symmetry or both; thereby producing a chiral, non-racemic compound; wherein said catalyst is a derivatized cinchona-alkaloid. Yet another aspect of the present invention relates to a method of kinetic resolution, comprising the step of: reacting a racemic cyclic anhydride with an alcohol in the presence of a derivatized cinchona-alkaloid catalyst.

  本发明的一个方面涉及基于金鸡纳碱的催化剂。本发明的第二个方面涉及通过将金鸡纳碱与碱和具有适当离去基团的化合物反应来制备衍生金鸡纳碱催化剂的方法。本发明的另一个方面涉及从一个前手循环酸酐或一个中间循环酸酐制备手性非拉克米化合物的方法，包括以下步骤：在催化剂的存在下，将前手循环酸酐或中间循环酸酐与亲核试剂反应；其中所述前手循环酸酐或中间循环酸酐包括一个内部对称平面或对称点或两者；从而产生手性非拉克米化合物；其中所述催化剂是衍生金鸡纳碱。本发明的另一个方面涉及一个动力学分辨的方法，包括以下步骤：在衍生金鸡纳碱催化剂的存在下，将拉克米循环酸酐与醇反应。
• 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。
• The use of chloroacetic acid in the mitsunobu reaction.
  作者：Mohamed Saïah、Michel Bessodes、Kostas Antonakis

  DOI：10.1016/s0040-4039(00)74249-3

  日期：1992.7

  Reaction of chloroacetic acid with TPP-DEAD was found to be very effective for the inversion of sterically congested alcohols, including carbohydrates and nucleosides.

  发现氯乙酸与TPP-DEAD的反应对于颠倒空间堵塞的醇（包括碳水化合物和核苷）非常有效。
• Monoterpenoid-based inhibitors of filoviruses targeting the glycoprotein-mediated entry process
  作者：Anastasiya S. Sokolova、Olga I. Yarovaya、Anastasiya V. Zybkina、Ekaterina D. Mordvinova、Nadezhda S. Shcherbakova、Anna V. Zaykovskaya、Dmitriy S. Baev、Tatyana G. Tolstikova、Dmitriy N. Shcherbakov、Oleg V. Pyankov、Rinat A. Maksyutov、Nariman F. Salakhutdinov

  DOI：10.1016/j.ejmech.2020.112726

  日期：2020.12

  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.
• Blanco, Jose M.; Caamano, Olga; Eirin, Ana, Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 12, p. 923 - 930
  作者：Blanco, Jose M.、Caamano, Olga、Eirin, Ana、Fernadez, Franco、Medina, Lucia

  DOI：——

  日期：——