(rac)-2-[(4-fluorophenyl)methyl]cyclohexan-1-one | 144147-62-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (rac)-2-[(4-fluorophenyl)methyl]cyclohexan-1-one
• 英文别名: 2-(4-fluorobenzyl)cyclohexanone；2-[(4-fluorophenyl)methyl]cyclohexan-1-one
• CAS: 144147-62-6
• 化学式: C₁₃H₁₅FO
• 分子量: 206.26
• InChiKey: XNPGRZDZXFLUQR-UHFFFAOYSA-N

物化性质

• 沸点：
  308.6±15.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (rac)-2-[(4-fluorophenyl)methyl]cyclohexan-1-one 在 盐酸 、 正丁基锂 、 三乙胺 、 二异丙胺 作用下， 反应 4.75h， 生成 7-(4-Fluoro-benzyl)-2-(4-fluoro-phenyl)-4,5,6,7-tetrahydro-2H-indazole-3-carbaldehyde
  参考文献：
  名称：

  HMG-CoA reductase inhibitors: design, synthesis, and biological activity of tetrahydroindazole-substituted 3,5-dihydroxy-6-heptenoic acid sodium salts

  摘要：

  Compounds comprising a series of 7-[2-(4-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-3,5-dihydroxy-6-heptenoic acid sodium salts (18) were synthesized and tested for their ability to inhibit HMG-CoA reductase in a partially purified enzyme preparation and cholesterol biosynthesis from acetate in cultured HEP-G2 cells. Changing the size of the saturated ring of the tetrahydroindazole nucleus did not improve potency, but incorporation of substituents at the 7-position resulted in up to 1700-fold improvement in inhibitory potency. Structure-activity studies revealed that the most potent compounds possess a substituted benzyl group at the 7-position, with a preference for steric bulk at the para position of the benzene ring. The most potent enzyme inhibitor (18t, IC50 = 3.0 nM) is approximately 3-fold more potent than lovastatin sodium salt (2). The most potent cholesterol biosynthesis inhibitor in HEP-G2 cells (18q, IC50 = 0.078 muM) is slightly less potent than 2 (sodium salt). Molecular modeling studies suggested that, when compared to the parent compound (18b) lacking the appropriate 7-substituent, 18t overlaps better with 2 and literature inhibitors 5 and 6 in a hydrophobic binding region adjacent to the enzyme active site.

  DOI：

  10.1021/jm00075a024
• 作为产物：
  描述：

  (E)-2-(4-fluoro-phenylmethylene)-cyclohexanol 以 正己烷 为溶剂， 生成 (rac)-2-[(4-fluorophenyl)methyl]cyclohexan-1-one
  参考文献：
  名称：

  取代基和溶剂极性对光化学[1,3]σ位移的影响。实验证据支持突发性事件的发生

  摘要：

  提供了有关在无环烯烃中突然极化的进一步实验证据。结果表明，分子内光化学[1,3] -OH的转变为1所生成的产物的产率仅取决于所用溶剂的极性。可以通过偶极溶剂分子的重新取向极化来稳定在辐射1时形成的两性离子中间体，从而很好地解释该结果。除此之外，发现在C 3 -C 9的末端碳原子处的烷基被取代。1中被苯基取代基形成的环外双键导致发生光化学[1,3] -H移位。取代基在环外双键上的这种指导作用可以在突然极化模型的基础上很好地解释。

  DOI：

  10.1016/s0040-4020(01)86197-4

文献信息

• Trialkylsilyl triflimides as easily tunable organocatalysts for allylation and benzylation of silyl carbon nucleophiles with non-genotoxic reagents
  作者：Oscar Mendoza、Guy Rossey、Léon Ghosez

  DOI：10.1016/j.tetlet.2010.03.030

  日期：2010.5

  Trialkylsilyl triflimides generated in situ are unique catalysts for the electrophilic benzylation or allylation of trialkylsilylenol ethers or allyl trialkylsilanes with non-genotoxic alkylating reagents such as benzyl and allyl acetates. In most cases the reactions are fast at room temperature and yields are high. The reaction works particularly well with electron-rich benzyl donors including derivatives

  原位生成的三烷基甲硅烷基三氟甲酸酯是独特的催化剂，用于三烷基甲硅烷基醚或烯丙基三烷基硅烷与非遗传毒性烷基化试剂（如乙酸苄基酯和乙酸烯丙酯）的亲电苄基化或烯丙基化。在大多数情况下，该反应在室温下反应很快，并且产率很高。该反应特别适用于富电子的苄基供体，包括吡咯，吲哚和呋喃的衍生物。
• Enantioselective Protonation of Enol Esters with Bifunctional Phosphonium/Thiourea Catalysts
  作者：Eiji Yamamoto、Kodai Wakafuji、Yusuke Mori、Gaku Teshima、Yuki Hidani、Makoto Tokunaga

  DOI：10.1021/acs.orglett.9b01216

  日期：2019.6.7

  Bifunctional phosphonium/thioureas derived from tert-leucine behaved as highly selective catalysts for enantioselective protonation of enol esters, providing α-chiral ketones in yields of up to 99% with high enantioselectivities (up to 98.5:1.5 er). Control experiments clarified that a bulky tert-butyl group and phosphonium and thiourea moieties were necessary to achieve such high stereoselectivity

  衍生自叔亮氨酸的双官能phospho /硫脲可作为烯醇酯对映选择性质子化的高选择性催化剂，以高对映选择性（高达98.5：1.5 er）提供α-手性酮，收率高达99％。对照实验表明，大的叔丁基基团以及phospho和硫脲部分对于实现如此高的立体选择性是必需的。此外，机理研究表明，该催化剂已转化为相应的甜菜碱，可作为单分子催化剂。
• <i>β</i>-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp)–H bonds using a palladium catalyst
  作者：Jing Peng、Chao Chen、Chanjuan Xi

  DOI：10.1039/c5sc03903g

  日期：——

  Palladium catalyzed selectiveβ-arylation of oxime ethers was realized using diaryliodonium salts as the key arylation reagents.

  钯催化的氧肟醚的选择性β-芳基化反应是利用二芳基碘盐作为关键的芳基化试剂实现的。
• Benzylcycloalkyl amines as modulators of chemokine receptor activity
  申请人：Wacker A. Dean

  公开号：US20050124671A1

  公开（公告）日：2005-06-09

  The present application describes modulators of CCR3 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of inflammatory diseases such as asthma and other allergic diseases.

  本申请描述了CCR3的调节剂，其化学式为(I):或其药学上可接受的盐形式，用于预防哮喘和其他过敏性疾病等炎症性疾病。
• Therapeutic amide derivatives
  申请人：Kawai Makoto

  公开号：US20070167452A1

  公开（公告）日：2007-07-19

  The present invention relates to compounds of the formula (I): or a pharmaceutically acceptable salt or solvate thereof, to processes for the preparation of, intermediates used in the preparation of, compositions containing such compounds and the uses of such compounds as antagonists of the NMDA NR2B receptor.

  本发明涉及式(I)的化合物：或其药学上可接受的盐或溶剂，以及制备这些化合物的过程中使用的中间体，含有这些化合物的组合物及其作为NMDA NR2B受体拮抗剂的用途。