2-(3-phenylpropyl)cyclopentanone | 162369-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-phenylpropyl)cyclopentanone
• 英文别名: 2-(3-phenyl-propyl)-cyclopentanone；2-(3-Phenyl-propyl)-cyclopentanon；2-(3-Phenyl-propyl)-cyclopentanon-(1)；2-(3-Phenylpropyl)cyclopentan-1-one
• CAS: 162369-31-5；15068-13-0
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: KKDMEAFRIMWZPP-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：
  4
• 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

反应信息

• 作为反应物：
  描述：

  2-(3-phenylpropyl)cyclopentanone 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 8-phenyl-5-oxooctanoic acid
  参考文献：
  名称：

  Bardhan,J.C. et al., Indian Journal of Chemistry, 1967, vol. 5, p. 100 - 102

  摘要：

  DOI：
• 作为产物：
  描述：

  1-碘-3-苯基丙烷 在 氢氧化钾 、 乙酸酐 作用下， 以 乙醇 为溶剂， 生成 2-(3-phenylpropyl)cyclopentanone
  参考文献：
  名称：

  Bardhan,J.C. et al., Indian Journal of Chemistry, 1967, vol. 5, p. 100 - 102

  摘要：

  DOI：

文献信息

• Intramolecular Reactions of Benzylic Azides with Ketones:  Competition between Schmidt and Mannich Pathways
  作者：Aaron Wrobleski、Jeffrey Aubé

  DOI：10.1021/jo001367p

  日期：2001.2.1

  The Lewis acid-promoted reactions of benzylic azides with ketones can proceed by two major pathways. The azido-Schmidt reaction involves simple addition of azide to the ketone followed by rearrangement and ring expansion. In addition, benzylic azides can undergo prior rearrangement to afford iminium ions that can subsequently participate in a Mannich reaction. A series of ketones containing an alpha CH2(CH2)nCH(N3)Ph

  路易斯酸促进的苄基叠氮化物与酮的反应可以通过两个主要途径进行。叠氮基-施密特反应涉及将叠氮化物简单地添加到酮中，然后重排和扩环。另外，苄基叠氮化物可先进行重排以提供亚胺离子，其随后可参与曼尼希反应。制备了一系列含有αCH2（ ）nCH（N3）Ph取代基（n = 1-3）的酮，以研究产物对酮环尺寸和系链长度的依赖性。对于所有检查的酮类，当使用四碳连接剂时（上述配方中的n = 1），由于分子内Schmidt反应而获得的双环内酰胺的收率很高，但曼尼希产品主要用于较长的拴系剂（n = 2，3）。 ）。
• Carboni, Gazzetta Chimica Italiana, 1952, vol. 82, p. 533,537
  作者：Carboni

  DOI：——

  日期：——
• Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Naoto Tominaga、Hiroshi Morita

  DOI：10.1021/jo00052a036

  日期：1992.12

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.
• Thiol-Catalyzed Acyl Radical Cyclization of Alkenals
  作者：Kazuya Yoshikai、Tomoharu Hayama、Katsumi Nishimura、Ken-ichi Yamada、Kiyoshi Tomioka

  DOI：10.1021/jo048275a

  日期：2005.1.1

  Thiol-catalyzed direct generation of acyl radicals and their intramolecular addition to olefins of alkenals gave 2-substituted five- and six-membered cyclic ketones in reasonably good yields. The combination of odorless tert-dodecanthiol and AIBN or V-40 was the initiator of choice among surveyed radical generators for the cyclization of alkenals. Aldehydes having electron-deficient olefins cyclized more easily than those having unactivated olefins.