2-苯乙基环己烷-1-酮 | 1138-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-苯乙基环己烷-1-酮
• 中文别名: 2-苯乙基环已醇-1-酮
• 英文名称: 2-phenethylcyclohexanone
• 英文别名: 2-(2-phenylethyl)cyclohexanone；2-Phenethyl-cyclohexanone；2-(2-phenylethyl)cyclohexan-1-one
• CAS: 1138-44-9
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: PEVNEAUCRZWXDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914299000

反应信息

• 作为反应物：
  描述：

  2-苯乙基环己烷-1-酮 在 盐酸 、 正丁基锂 、 sodium acetate 、 sodium hydride 、 二异丁基氢化铝 、 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.25h， 生成 (E)-3-[2-(4-Fluoro-phenyl)-7-phenethyl-4,5,6,7-tetrahydro-2H-indazol-3-yl]-prop-2-en-1-ol
  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：

  邻氯乙苯 在 仲丁基锂 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 25.0h， 以58%的产率得到2-苯乙基环己烷-1-酮
  参考文献：
  名称：

  Tetrahydro-indazole cannabinoid modulators

  摘要：

  这项发明涉及一种式I的四氢吲哚类大麻素调节剂化合物，以及一种用于治疗、改善或预防大麻素受体介导的综合症、紊乱或疾病的方法。

  公开号：

  US20050228034A1

文献信息

• Titanocene(II)-promoted desulfurizative acylation of thioacetals with alkanenitriles
  作者：Takeshi Takeda、Haruhiko Taguchi、Tooru Fujiwara

  DOI：10.1016/s0040-4039(99)02001-8

  日期：2000.1

  Ketones were obtained in good yields by titanocene(II)-promoted reaction of thioacetals with alkanenitriles. The regioselective formation of α-substituted ketone was observed when the reaction was carried out in the presence of methyl iodide or benzyl bromide.

  通过钛茂（II）促进的硫代缩醛与链烯腈的反应，可以得到高收率的酮。当在甲基碘或苄基溴的存在下进行反应时，观察到α-取代的酮的区域选择性形成。
• α-Alkylation of Ketones by Addition of Zinc Enamides to Unactivated Olefins
  作者：Masaharu Nakamura、Takuji Hatakeyama、Eiichi Nakamura

  DOI：10.1021/ja0465193

  日期：2004.9.1

  A zinc enamide generated from the corresponding N-aryl imine undergoes addition to an unactivated olefin, such as ethylene, 1-octene, and isobutylene, to generate an alpha-alkylated gamma-zincioimine intermediate in good to excellent yield. Terminal and gem-disubstituted olefins react with >99% regioselectivity, allowing the C-C bond formation to take place at the more hindered carbon of the double

  由相应的 N-芳基亚胺生成的锌烯酰胺与未活化的烯烃（例如乙烯、1-辛烯和异丁烯）加成，以良好至极好的收率生成 α-烷基化 γ-锌亚胺中间体。末端和偕二取代的烯烃以>99% 的区域选择性反应，使得 CC 键的形成发生在双键的受阻更大的碳上。有机锌中间体与碳亲电子试剂进一步形成 CC 键，在亚胺水解后，生成带有各种官能化伯、仲和叔烷基的 α-烷基化酮。
• α-Alkylation of Ketones with Alkenes Enabled by Photoinduced Activation of Silyl Enol Ethers in the Presence of a Small Amount of Water
  作者：Tsubasa Hirata、Yoshihiro Ogasawara、Yasuhiro Yamashita、Shu̅ Kobayashi

  DOI：10.1021/acs.orglett.1c01824

  日期：2021.8.6

  Under blue-light irradiation conditions with a photocatalyst [1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene], silyl enol ethers reacted with alkenes in the presence of a small amount of water to afford the α-alkylation products in good to high yields. A thiol cocatalyst was found to expand the substrate scope of the reaction.

  在光催化剂[1,2,3,5-四(咔唑-9-基)-4,6-二氰基苯]的蓝光照射条件下，甲硅烷基烯醇醚在少量水存在下与烯烃反应生成以良好到高产率提供α-烷基化产物。发现硫醇助催化剂扩大了反应的底物范围。
• Electroorganic chemistry. 98. Novel intramolecular stereoselective addition of electrogenerated radical species to the aromatic ring
  作者：Tatsuya. Shono、Naoki. Kise、Takeshi. Suzumoto、Toshio. Morimoto

  DOI：10.1021/ja00275a084

  日期：1986.7

  La reduction electrochimique de derives de l'aryl-5 pentanone-2 conduit a des derives de l'(hexahydro-1,2,3,4,6,8a methyl-1) naphtol-1

  La 还原电化学 de 衍生 de l'aryl-5 pentanone-2 导管 a des 衍生 de l'(hexahydro-1,2,3,4,6,8amethyl-1)naphtol-1
• Alkyl radical cyclisations of methylenecyclopropane derivatives
  作者：Christine Destabel、Jeremy D Kilburn、John Knight

  DOI：10.1016/s0040-4020(01)89429-1

  日期：1994.1

  Radical cyclisations of various methylenecyclopropane derivatives have been studied. Cyclisation of diphenylsubstituted (methylenecyclopropyl)butyl radical 10 gave the unexpected cyclohexene 5, via a series of radical rearrangements. In further studies, (methylenecyclopropyl) radicals underwent exclusive 5-exo cyclisation, while (methylenecyclopropyl)butyl radicals gave mixtures of products resulting

  已经研究了各种亚甲基环丙烷衍生物的自由基环化。diphenylsubstituted（methylenecyclopropyl）的环化丁基自由基10，得到意想不到的环己烯5，经由一系列自由基重排。在进一步的研究中，对（亚甲基环丙基）自由基进行了专门的5- exo环化反应，而（亚甲基环丙基）丁基则给出了由6- exo和7-内环化反应生成的产物的混合物。在（亚甲基环丙基）-戊基自由基的尝试环化中未检测到环化产物。