cyclopentyl-(2-hydroxy-phenyl)-methanone | 51795-96-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclopentyl-(2-hydroxy-phenyl)-methanone
• 英文别名: cyclopentyl(2-hydroxyphenyl)methanone；cyclopentyl-(2-hydroxy-phenyl)-ketone；Cyclopentyl-(2-hydroxy-phenyl)-keton；Cyclopentyl-o-hydroxyphenylketon；cyclopentyl-(2-hydroxyphenyl)methanone
• CAS: 51795-96-1
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: FHUXPGWBJXGPSP-UHFFFAOYSA-N

物化性质

• 沸点：
  125-135 °C(Press: 13 Torr)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  cyclopentyl-(2-hydroxy-phenyl)-methanone 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 2,2-spiropentanylbenzofuran-3-one
  参考文献：
  名称：

  Unexpected Migration and Oxidative Cyclization of Substituted 2-Acetophenone Triflates under Basic Conditions:  Synthetic and Mechanistic Insights

  摘要：

  Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 degreesC. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions. Potential mechanistic pathways are evaluated.

  DOI：

  10.1021/jo0352023
• 作为产物：
  描述：

  1-环戊烯羧酸 在 甲醇 、 Pt/Al₂O₃ 、 氯化亚砜 、 colloid 作用下， 生成 cyclopentyl-(2-hydroxy-phenyl)-methanone
  参考文献：
  名称：

  Skraup; Binder, Chemische Berichte, 1929, vol. 62, p. 1135

  摘要：

  DOI：

文献信息

• Intermolecular C–O addition of carboxylic acids to arynes: synthesis of o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones
  作者：Anton V. Dubrovskiy、Richard C. Larock

  DOI：10.1016/j.tet.2013.01.078

  日期：2013.4

  An efficient and simple route to biologically and pharmaceutically important o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones has been developed utilizing readily available carboxylic acids and commercially available o-(trimethylsilyl)aryl triflates.

  利用现成的羧酸和市售的邻(三甲基甲硅烷基)芳基三氟甲磺酸酯，开发了一种有效且简单的途径来生产生物学和药学上重要的邻羟基芳基酮、呫吨酮、 4-色满酮和黄酮。
• Intermolecular C−O Addition of Carboxylic Acids to Arynes
  作者：Anton V. Dubrovskiy、Richard C. Larock

  DOI：10.1021/ol101017z

  日期：2010.7.16

  A novel, efficient, and expedient route to biologically and pharmaceutically important o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones has been developed starting from readily available carboxylic acids and commercially available o-(trimethylsilyl)aryl triflates.

  从容易获得的羧酸和市售的邻-(三甲基甲硅烷基)芳基三氟甲磺酸酯开始，已经开发出一种新颖、有效和方便的途径来制备生物学和药学上重要的邻羟基芳基酮、氧杂蒽酮、4-色满酮和黄酮。
• Visible-light-driven site-selective alkylation of the benzo core of coumarins
  作者：Krishna N. Tripathi、Shashank Singh、Naved Akhtar、Kuntal Manna、Ravi P. Singh

  DOI：10.1039/d2cc03073j

  日期：——

  An unprecedented, straightforward photochemical platform for efficient site-selective C–H alkylation of the C7 position of the benzocore via the cross coupling between coumarins and NHPI esters, employing Ru(II) as a photocatalyst in visible light, has been reported. Remarkably, this transformation demonstrated broad substrate scope and good functional group compatibility. Controlled experiments and

  已经报道了一种前所未有的、直接的光化学平台，通过香豆素和 NHPI 酯之间的交叉偶联，使用 Ru( II ) 作为可见光下的光催化剂，对苯并核的 C7 位进行有效的位点选择性 C-H 烷基化。值得注意的是，这种转化表现出广泛的底物范围和良好的官能团兼容性。受控实验和 DFT 计算揭示了对反应机理细节的一些见解，并使我们能够提出区域选择性的合理机制。
• Gold self-relay catalysis enabling annulative oxygenation of propargylic alcohols with O-nucleophiles
  作者：Meng-Ying Hao、Yin Zhang、Na Lin、Rong Fu、Xiao-Shuang Ji、Bo Jiang、Shu-Jiang Tu、Wen-Juan Hao

  DOI：10.1039/d3cc00089c

  日期：——

  A new gold(I) self-relay catalysis reaction enabling the annulative oxygenation of propargylic alcohols with various O-nucleophiles, such as carboxylic acids, alcohols and TBHP, is reported, producing a series of functionalized benzofurans in moderate to good yields under mild conditions. This protocol benefits from the π- and σ-Lewis acid capability of gold complexes, demonstrating high molecular

  据报道，一种新的金 ( I ) 自继电器催化反应能够使炔丙醇与各种 O-亲核试剂（如羧酸、醇和 TBHP）发生环氧化反应，从而在温和条件下以中等至良好的收率生产一系列功能化的苯并呋喃. 该协议受益于金配合物的 π- 和 σ-Lewis 酸能力，展示了高分子收敛性、广泛的底物灵活性、高官能团兼容性和温和的条件。
• Synthesis of Ketones through Microwave Irradiation Promoted Metal-Free Alkylation of Aldehydes by Activation of C(sp³)–H Bond
  作者：Xinying Zhang、Zhangxin Wang、Xuesen Fan、Jianji Wang

  DOI：10.1021/acs.joc.5b01824

  日期：2015.11.6

  In this paper, a novel methodology for the synthesis of ketones via microwave irradiation promoted direct alkylation of aldehydes by activation of the inert C(sp(3))-H bond has been developed. Notably, the reactions were accomplished under metal-free conditions and used commercially available aldehydes and cycloalkanes as substrates without prefunctionalization. By using this novel method, an alternative synthetic approach toward the key intermediates for the preparation of the pharmaceutically valuable oxaspiroketone derivatives was successfully established.