2-<2-Chlor-benzyl>-cyclohexanon | 2702-77-4

• 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: 2-<2-Chlor-benzyl>-cyclohexanon
• 英文别名: 2-(2-Chlor-benzyl)-cyclohexanon；2-[(2-chlorophenyl)methyl]cyclohexan-1-one
• CAS: 2702-77-4
• 化学式: C₁₃H₁₅ClO
• 分子量: 222.715
• InChiKey: OYYZUAGSPRPUCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  1

反应信息

• 作为反应物：
  描述：

  2-<2-Chlor-benzyl>-cyclohexanon 在 正丁基锂 、 三乙胺 、 二异丙胺 作用下， 以 乙醇 为溶剂， 反应 0.75h， 生成 7-(2-Chloro-benzyl)-3-dimethoxymethyl-2-(4-fluoro-phenyl)-4,5,6,7-tetrahydro-2H-indazole
  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：

  在 盐酸 、 聚合甲醛 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以69%的产率得到2-<2-Chlor-benzyl>-cyclohexanon
  参考文献：
  名称：

  β-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp)–H bonds using a palladium catalyst

  摘要：

  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。

  DOI：

  10.1039/c5sc03903g

文献信息

• Fusco,R. et al., Farmaco, Edizione Scientifica, 1965, vol. 20, p. 393 - 407
  作者：Fusco,R. et al.

  DOI：——

  日期：——
• HMG-CoA reductase inhibitors: design, synthesis, and biological activity of tetrahydroindazole-substituted 3,5-dihydroxy-6-heptenoic acid sodium salts
  作者：Peter J. Connolly、Claudia D. Westin、Deborah A. Loughney、Lisa K. Minor

  DOI：10.1021/jm00075a024

  日期：1993.11

  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.
• <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。