(2-(furan-2-yl)cyclopropyl)(phenyl)methanone | 75491-29-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-(furan-2-yl)cyclopropyl)(phenyl)methanone
• 英文别名: Phenyl 2-(2'-furanyl)cyclopropyl ketone；[2-(furan-2-yl)cyclopropyl]-phenylmethanone
• CAS: 75491-29-1
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: YLUQCVINWJOJKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-(furan-2-yl)cyclopropyl)(phenyl)methanone 、 苯乙炔 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以86%的产率得到1-(2-(furan-2-yl)cyclopropyl)-1,3-diphenylprop-2-yn-1-ol
  参考文献：
  名称：

  Au(iii)-catalyzed ring opening reaction of 1-cyclopropyl-2-yn-1-ols with nucleophiles: highly efficient approach to (Z)-conjugated enynes

  摘要：

  在温和的条件下，利用 Au（III）催化的 1-环丙基-2-炔-1-醇与亲核物的开环反应，开发出了一种高效的 (Z) 共轭烯炔化合物的制备方法。

  DOI：

  10.1039/b714511j
• 作为产物：
  描述：

  (2E)-3-(2-呋喃基)-1-苯基-2-丙烯-1-酮 、 三甲基碘化亚砜 在 sodium hydride 作用下， 以 二甲基亚砜 、 mineral oil 为溶剂， 反应 5.25h， 以85%的产率得到(2-(furan-2-yl)cyclopropyl)(phenyl)methanone
  参考文献：
  名称：

  可见光诱导的三元催化环丙基酮的开环氰化反应。

  摘要：

  描述了用于构建γ-氰基酮的前所未有的三丙基环酮催化三价催化，一般的开环氰化反应。关键是将光氧化还原催化与路易斯酸催化和铜催化合并，以实现碳-碳键的选择性裂解以及生成的自由基和氰化物阴离子的选择性偶联。

  DOI：

  10.1039/d0cc05167e

文献信息

• Improved Dimethylsulfoxonium Methylide Cyclopropanation Procedures, Including a Tandem Oxidation Variant
  作者：Richard Taylor、Richard Paxton

  DOI：10.1055/s-2007-967966

  日期：——

  for the cyclopropanation of α,β-unsaturated carbonyl compounds and related systems is described which employs trimethylsulfoxonium iodide and an organic base in acetonitile to generate dimethylsulfoxonium methylide in situ; in addition, preliminary results are described in which activated alcohols are converted directly into cyclopropyl ketones by a one-pot tandem oxidation-cyclopropanation sequence

  描述了一种用于α,β-不饱和羰基化合物环丙烷化的新方法和相关系统，该方法采用碘化三甲基亚砜和有机碱在乙腈中原位生成甲基亚砜；此外，还描述了初步结果，其中活化的醇通过一锅串联氧化 - 环丙烷化序列直接转化为环丙基酮。
• Chalcone-Based Synthesis of Tetrahydropyridazines via Cloke–Wilson-Type Rearrangement-Involved Tandem Reaction between Cyclopropyl Ketones and Hydrazines
  作者：Yingfen Meng、Jiayi Gu、Meixiu Xin、Yi Jiang、Zhibo Du、Guoqing Lu、Jiayao Jiang、Albert S. C. Chan、Zhuofeng Ke、Yong Zou

  DOI：10.1021/acs.joc.3c02824

  日期：2024.2.16

  A facile and efficient approach for the synthesis of multisubstituted tetrahydropyridazines starting from cyclopropyl ketones and hydrazines has been developed. The transformation is chalcone-based and takes place via a Cloke–Wilson-type rearrangement-involved tandem reaction catalyzed by TfOH in HFIP.

  开发了一种以环丙基酮和肼为原料合成多取代四氢哒嗪的简便有效的方法。该转化基于查尔酮，通过 HFIP 中 TfOH 催化的 Cloke-Wilson 型重排串联反应发生。
• Highly Efficient Synthesis of Tri- and Tetrasubstituted Conjugated Enynes from Brønsted Acid Catalyzed Alkoxylation of 1-Cyclopropylprop-2-yn-1-ols with Alcohols
  作者：Srinivasa Reddy Mothe、Philip Wai Hong Chan

  DOI：10.1021/jo9008244

  日期：2009.8.21

  A highly efficient triflic acid catalyzed ring opening of a wide variety of 1-cyclopropyl-2-propyn-1-ols with alcohols as an efficient synthetic route to conjugated enynes is reported herein. The reaction was operationally straight forward and accomplished in good to excellent yields (44-100%,), high product turnovers (up to 10,000), and with complete regioselectivity under mild conditions with a low catalyst loading of 0.01 mol%. The mechanism is suggested to involve protonation of the alcohol substrate by the TfOH catalyst, followed by ionization of the starting material. This causes ring opening, of the cyclopropane moiety and trapping by the alcohol nucleophile to give the conjugated enyne product. The synthetic utility Of the present method was also exemplified by the efficient large-scale Conversion in grain quantities of one example studied in this work to the corresponding conjugated enyne product in excellent yield and turnover number.
• Synthesis and mass spectra of furylcyclopropyl and furfurylidene ketones
  作者：V. I. Kadentsev、V. D. Sokovykh、O. S. Chizhov、V. M. Shostakovskii、R. M. Carlson

  DOI：10.1007/bf00958811

  日期：1980.6
• Paira; Mandal; Roy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 5, p. 573 - 577
  作者：Paira、Mandal、Roy

  DOI：——

  日期：——