2-(2-naphthylmethyl)cyclohexanone | 101594-25-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-naphthylmethyl)cyclohexanone
• 英文别名: 2-[2]Naphthylmethyl-cyclohexanon；2-(Naphthalen-2-ylmethyl)cyclohexan-1-one
• CAS: 101594-25-6
• 化学式: C₁₇H₁₈O
• 分子量: 238.329
• InChiKey: MXAXTPGPMJAEJP-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60 °C(Solv: water (7732-18-5); methanol (67-56-1))
• 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：
  0.35
• 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-naphthylmethyl)cyclohexanone 在 硫酸 、 苯 作用下， 生成 8,9,10,11-tetrahydro-7H-benzo[c]fluorene
  参考文献：
  名称：

  622. 3：4-苯并芴及其一些单甲基衍生物的合成

  摘要：

  DOI：

  10.1039/jr9570003181
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 Pd/SrCO₃ 、 乙酸乙酯 作用下， 生成 2-(2-naphthylmethyl)cyclohexanone
  参考文献：
  名称：

  622. 3：4-苯并芴及其一些单甲基衍生物的合成

  摘要：

  DOI：

  10.1039/jr9570003181

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。
• [EN] COMPOUND HAVING CHIRAL SPIROBIINDANE SKELETON AND PREPARATION METHOD THEREFOR<br/>[FR] COMPOSÉ PRÉSENTANT UN SQUELETTE SPIROBIINDANE CHIRAL ET SON PROCÉDÉ DE PRÉPARATION<br/>[ZH] 手性螺二氢茚骨架化合物及其制备方法
  申请人：ZHEJIANG JIUZHOU PHARM CO LTD

  公开号：WO2017107789A1

  公开（公告）日：2017-06-29

  本发明公开了一种手性螺二氢茚骨架化合物及其制备方法。本发明的手性稠环螺二氢茚骨架化合物如式I或I'所示；本发明的手性螺二氢茚骨架化合物的制备方法，其包括如下步骤：溶剂中，催化剂作用下，将如式III所示的化合物进行分子内傅里德-克拉夫茨反应，制得如式I所示的化合物；所述催化剂为布朗斯特酸或路易斯酸。本发明的制备方法，不需采用手性起始原料或手性拆分试剂、无须进行手性拆分步骤、方法简单、后处理简便、经济环保、产物收率高、产物光学纯度和化学纯度高。采用本发明的手性稠环螺二氢茚骨架化合物制得的过渡金属催化的不对称反应的催化剂，催化效果显著，产物收率＞99％，产物ee值高达＞99％。
• Nickel‐Catalyzed Enantioselective α‐Allylation of Cyclic Ketones with Allylic Alcohols
  作者：Neng‐Quan Jiang、Ming‐Ming Li、Li‐Jun Xiao、Qi‐Lin Zhou

  DOI：10.1002/adsc.202400538

  日期：——

  reaction often necessitated the use of activated ketones or pre-prepared enol intermediates as substrates. In this study, we developed a nickel-catalyzed α-allylation of unactivated cycloketones with allylic alcohols to synthesize chiral cycloketones with an α-quaternary carbon center. The reaction affords the products with 42–97% yields, 72–86% ee, and no additive is needed, and the only by-product is water

  过渡金属催化的酮的不对称 α-烯丙基化是通过 C−C 键形成构建立体中心的特别有用的工具。然而，此类反应通常需要使用活化的酮或预先制备的烯醇中间体作为底物。在这项研究中，我们开发了未活化环酮与烯丙醇的镍催化α-烯丙基化反应，以合成具有α-季碳中心的手性环酮。该反应产物收率42-97%，ee 72-86%，不需要任何添加剂，唯一的副产物是水。
• 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.
• A new general synthesis of polycyclic aromatic compounds based on enamine chemistry
  作者：Ronald G. Harvey、John Pataki、Cecilia Cortez、Pasquale Di Raddo、Cheng Xi Yang

  DOI：10.1021/jo00003a050

  日期：1991.2

  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.