2-(1-naphthylmethyl)cyclohexanone | 113777-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-naphthylmethyl)cyclohexanone
• 英文别名: 2-[(Naphthalen-1-yl)methyl]cyclohexan-1-one；2-(naphthalen-1-ylmethyl)cyclohexan-1-one
• CAS: 113777-19-8
• 化学式: C₁₇H₁₈O
• mdl: MFCD13477759
• 分子量: 238.329
• InChiKey: FGTXWXTUAZKBII-UHFFFAOYSA-N

物化性质

• 沸点：
  401.7±14.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.352
• 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-(1-naphthylmethyl)cyclohexanone 在 sodium hydroxide 、 sodium acetate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 1-(4-Fluoro-phenyl)-7-naphthalen-1-ylmethyl-4,5,6,7-tetrahydro-1H-indazole-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and progesterone receptor binding affinity of substituted 1-phenyl-7-benzyl-4,5,6,7-tetrahydro-1-indazoles

  摘要：

  Research directed toward the discovery of non-steroidal ligands for steroid receptors led to the preparation of a series of substituted 1-phenyl-7-benzyltetrahydroindazole-3-carboxaldehydes. Appropriately substituted 3-formyl analogs (4) were found to bind with high affinity to progesterone receptors and showed agonist activity in human T47D cells but were inactive in several in vivo models for progestational activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10016-6
• 作为产物：
  描述：

  1-吡咯烷-1-环己烯 、 1-溴甲基萘 以 1,4-二氧六环 为溶剂， 以86%的产率得到2-(1-naphthylmethyl)cyclohexanone
  参考文献：
  名称：

  A new general synthesis of polycyclic aromatic compounds based on enamine chemistry

  摘要：

  Alkylation of enamines and enamine salts by benzylic and (beta-haloethyl)aryl halides, respectively, followed by acidic cyclodehydration and dehydrogenation provides an efficient synthetic approach to a wide range of polycyclic aromatic compounds of diverse structural types. Specific polycyclic hydrocarbons synthesized by this route include benzo[a]- and benzo[c]fluorene, 7H-dibenzo[c,g]-, 13H-dibenzo[a,i]-, and 13H-dibenzo[a,g]fluorene, 15H-tribenzo[a,c,i]fluorene, dibenzo[b,def]chrysene, benzo[rst]pentaphene, indeno[1,2-b]fluorene, fluoreno[3,4-c]fluorene, octahydrodibenz[a,j]anthracene, dibenz[a,j]anthracene, octahydrodibenz[a,h]anthracene, dibenz[a,h]anthracene, dibenz[a,h]anthracene, picene, benzo[c]picene, 1H-benz[bc]aceanthrylene, and 4H-cyclopenta[def]chrysene. This method with appropriate modifications appears to be potentially broader in scope than established traditional methods of polycyclic hydrocarbon synthesis.

  DOI：

  10.1021/jo00003a050

文献信息

• Synthesis of polycyclic xanthenes and furans via palladium-catalyzed cyclization of polycyclic aryltriflate esters
  作者：Ji-Quan Wang、Ronald G Harvey

  DOI：10.1016/s0040-4020(02)00534-3

  日期：2002.7

  Palladium-catalyzed cyclization of polycyclic aromatic o-(arylmethyl)phenol triflate esters takes place with unexpected sulfur–oxygen bond cleavage to furnish polycyclic xanthenes. These are the first examples of Pd-catalyzed cross-coupling of aryl triflate esters with arenes to form diaryl ethers. In contrast, analogous palladium-catalyzed cyclization of polycyclic o-(aryloxy)phenol triflate esters

  钯催化的多环芳族邻-（芳基甲基）苯酚三氟甲酸酯酯的环化反应发生意外的硫-氧键裂解，从而提供了多环黄嘌呤。这些是芳基三氟甲磺酸酯与芳烃经钯催化交联形成二芳基醚的第一个例子。相反，类似的钯催化多环邻-（芳氧基）苯酚三氟甲酸酯酯的环化反应是通过一种机理进行的，该机理涉及常规的碳-氧键裂解，以提供二芳基呋喃。
• Palladium-catalyzed arylation of siloxycyclopropanes with aryl triflates. Carbon chain elongation via catalytic carbon-carbon bond cleavage
  作者：Satoshi. Aoki、Tsutomu. Fujimura、Eiichi. Nakamura、Isao. Kuwajima

  DOI：10.1021/ja00218a048

  日期：1988.5

  La reaction a une utilite synthetique generale et permet d'obtenir des composes carbonyles (cetones, aldehydes, esters) β-aryles

  La 反应 a une utilite synthetique generale et permet d'obtenir des composes carbonyles (cetones, aldehydes,esters) β-aryles
• 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.
• HARYEY, RONALD G.;PATAKI, JOHN;CORTEZ, CECILIA;DI, RADDO PASQUALE;YANG, C+, J. ORG. CHEM., 56,(1991) N, C. 1210-1217
  作者：HARYEY, RONALD G.、PATAKI, JOHN、CORTEZ, CECILIA、DI, RADDO PASQUALE、YANG, C+

  DOI：——

  日期：——
• AOKI, SATOSHI;FUJIMURA, TSUTOMU;NAKAMURA, EIICHI;KUWAJIMA, ISAO, J. AMER. CHEM. SOC., 110,(1988) N 10, 3296-3298
  作者：AOKI, SATOSHI、FUJIMURA, TSUTOMU、NAKAMURA, EIICHI、KUWAJIMA, ISAO

  DOI：——

  日期：——