2-环己基-1-(2-羟基-苯基)乙酮 | 1414926-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-环己基-1-(2-羟基-苯基)乙酮
• 英文名称: 2-cyclohexyl-1-(2-hydroxy-phenyl)ethanone
• 英文别名: 2-cyclohexyl-1-(2-hydroxyphenyl)ethan-1-one；2-Cyclohexyl-1-(2-hydroxyphenyl)ethanone；2-cyclohexyl-1-(2-hydroxyphenyl)ethanone
• CAS: 1414926-65-0
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: MTZCULKBCXZEHR-UHFFFAOYSA-N

物化性质

• 沸点：
  337.8±15.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-环己基-1-(2-羟基-苯基)乙酮 在 palladium on carbon 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 35.0~60.0 ℃ 、230.0 kPa 条件下， 反应 0.5h， 生成 3-环己基-2-(2-羟苯基)-1H-吲哚-6-羧酸甲酯
  参考文献：
  名称：

  An Efficient Process for the Large-Scale Synthesis of a 2,3,6-Trisubstituted Indole

  摘要：

  The efficient synthesis of a key trisubstituted indole intermediate 1 is described. The synthetic route required the use of an aryl Grignard reagent which was not commercially available, and the large-scale formation of this fragment and the thermal evaluation for this step is presented. The key step in the sequence was a Truce-Smiles rearrangement to provide an advanced ketone intermediate which, upon reduction, cyclized to the desired indole 1. Design of experiment (DoE) optimization of this reduction is also presented. In total >50 kg of target indole 1 were synthesized in 55% overall yield over five steps using this new route.

  DOI：

  10.1021/op300303p
• 作为产物：
  描述：

  环己基乙酸 在 甲烷磺酸 、 氢溴酸 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 2.67h， 生成 2-环己基-1-(2-羟基-苯基)乙酮
  参考文献：
  名称：

  An Efficient Process for the Large-Scale Synthesis of a 2,3,6-Trisubstituted Indole

  摘要：

  The efficient synthesis of a key trisubstituted indole intermediate 1 is described. The synthetic route required the use of an aryl Grignard reagent which was not commercially available, and the large-scale formation of this fragment and the thermal evaluation for this step is presented. The key step in the sequence was a Truce-Smiles rearrangement to provide an advanced ketone intermediate which, upon reduction, cyclized to the desired indole 1. Design of experiment (DoE) optimization of this reduction is also presented. In total >50 kg of target indole 1 were synthesized in 55% overall yield over five steps using this new route.

  DOI：

  10.1021/op300303p

文献信息

• Nickel-Catalyzed Directed Cross-Electrophile Coupling of Phenolic Esters with Alkyl Bromides
  作者：Feiyan Yang、Decai Ding、Chuan Wang

  DOI：10.1021/acs.orglett.0c03342

  日期：2020.12.4

  electrophilic acyl source in the reaction with diverse primary and secondary unactivated alkyl bromides. The cleavage of the relatively inert C–O bond is facilitated by the neighboring coordinating hydroxyl or sulfonamide moiety. By circumventing the use of pregenerated organometallics, this method allows efficient preparation of a variety of o-hydroxyl and tosyl-protected o-amino aryl ketones with high compatibility

  在本文中，我们证明了在各种伯和仲未活化烷基溴的反应中，成功使用了强健的酚酯作为亲电子酰基源。相邻的羟基或磺酰胺部分可促进相对惰性的C-O键的裂解。通过避免使用预生成的有机金属，该方法可以有效地制备具有高相容性和广泛功能的各种邻羟基和甲苯磺酰基保护的邻氨基芳基酮。
• Relay Catalysis by Achiral Borane and Chiral Phosphoric Acid in the Metal-Free Asymmetric Hydrogenation of Chromones
  作者：Jingjing Chen、Bochao Gao、Xiangqing Feng、Wei Meng、Haifeng Du

  DOI：10.1021/acs.orglett.1c03286

  日期：2021.11.5

  achiral borane and chiral phosphoric acid was successfully developed for the asymmetric hydrogenation of chromones, giving the desired products in high yields with up to 95% ee. Achiral borane and chiral phosphoric acid are highly compatible in this reaction. The achiral borane acts as a Lewis acid for the first-step hydrogenation, and the chiral phosphoric acid acts as an effective chiral proton shuttle

  成功开发了一种非手性硼烷和手性磷酸的中继催化策略，用于色酮的不对称氢化，以高达 95% 的 ee 的高收率得到所需产物。非手性硼烷和手性磷酸在该反应中高度相容。非手性硼烷作为第一步氢化的路易斯酸，手性磷酸作为有效的手性质子穿梭来控制对映选择性。
• NOVEL KINASE MODULATORS
  申请人：Rhizen Pharmaceuticals SA

  公开号：US20140080827A1

  公开（公告）日：2014-03-20

  The present invention provides PI3K protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.

  本发明提供了PI3K蛋白激酶调节剂，其制备方法，包含它们的药物组合物以及使用它们治疗、预防和/或改善激酶介导的疾病或疾病的方法。
• Synthesis of Tetrasubstituted Enamines through Borane-Catalyzed Hydrogenations
  作者：Zijia Zhang、Xiangqing Feng、Haifeng Du

  DOI：10.1021/acs.orglett.3c03578

  日期：2023.12.29

  This paper describes a B(C6F5)3-catalyzed hydrogenation of β-substituted α,β-unsaturated imines by using as low as 0.2 mol % catalyst. A variety of tetrasubstituted enamines were afforded in 95–99% yields. It provides an efficient and facile way without the need for column chromatography purification.

  本文描述了使用低至0.2 mol% 的催化剂进行B(C 6 F 5 ) 3催化的β-取代的α,β-不饱和亚胺的氢化反应。多种四取代烯胺的产率达到 95-99%。它提供了一种有效且简便的方法，无需柱色谱纯化。
• PROCESS FOR PREPARATION OF OPTICALLY PURE AND OPTIONALLY SUBSTITUTED 2-(1-HYDROXY-ALKYL)-CHROMEN-4-ONE DERIVATIVES AND THEIR USE IN PREPARING PHARMACEUTICALS
  申请人：Rhizen Pharmaceuticals S.A.

  公开号：EP2844647B1

  公开（公告）日：2020-07-22