3-benzoyloxy-2-cyclopenten-1-one | 73039-22-2

• 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: 3-benzoyloxy-2-cyclopenten-1-one
• 英文别名: 3-Benzoyloxy-2-cyclopentene-1-on；(3-oxocyclopenten-1-yl) benzoate
• CAS: 73039-22-2
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: VILPDSBJNPWNKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzoyloxy-2-cyclopenten-1-one 以 四氢呋喃 、 乙醚 、 环己烷 、 甲苯 为溶剂， 反应 6.5h， 生成 (1SR,2RS,3SR,6RS,7RS)-tricyclo<5.3.0.0^2,6>decane-3-spiro-2'-oxiran-6-yl benzoate
  参考文献：
  名称：

  A short enantiospecific route to isodaucane sesquiterpenes from limonene. On the absolute configuration of (+)-aphanamol I and II.

  摘要：

  The isodaucane sesquiterpenes (+)-aphanamol I (3) and (-)-2-oxoisodauc-5-en-12-al [(-)-6] have been prepared in a short reaction sequence from 5(S)-isopropyl-2-methyl-l-cyclopentene-1-carbaldehyde (S)-23 (readily obtainable from (+)-limonene). Key steps were a de Mayo type photocyclization of an 3-acyloxy-2-cyclopenten-1-one with 3(S)-isopropyl-1-methylcyclopentene [(S)-24] to a [5.3.0.0(2.6)]tricyclodecanone (e.g., (-)-28) with the desired configuration at all stereocenters and the formation of 3 by a base-catalyzed fragmentation of the gamma,delta-epoxyalcohol intermediate 33 (R = H), which produced all the desired functional groups in one step. The stereochemical assignments were supported by CD data as well as by the synthesis of (-)-norbourbonone (29) from (S)-24, which is a novel chiral intermediate. These results are in confliction with some earlier assignmnents of the absolute configuration in the isodaucane group of sesquiterpenes.

  DOI：

  10.1021/jo00046a018
• 作为产物：
  描述：

  1,3-环戊二酮 、 苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以88%的产率得到3-benzoyloxy-2-cyclopenten-1-one
  参考文献：
  名称：

  A short enantiospecific route to isodaucane sesquiterpenes from limonene. On the absolute configuration of (+)-aphanamol I and II.

  摘要：

  The isodaucane sesquiterpenes (+)-aphanamol I (3) and (-)-2-oxoisodauc-5-en-12-al [(-)-6] have been prepared in a short reaction sequence from 5(S)-isopropyl-2-methyl-l-cyclopentene-1-carbaldehyde (S)-23 (readily obtainable from (+)-limonene). Key steps were a de Mayo type photocyclization of an 3-acyloxy-2-cyclopenten-1-one with 3(S)-isopropyl-1-methylcyclopentene [(S)-24] to a [5.3.0.0(2.6)]tricyclodecanone (e.g., (-)-28) with the desired configuration at all stereocenters and the formation of 3 by a base-catalyzed fragmentation of the gamma,delta-epoxyalcohol intermediate 33 (R = H), which produced all the desired functional groups in one step. The stereochemical assignments were supported by CD data as well as by the synthesis of (-)-norbourbonone (29) from (S)-24, which is a novel chiral intermediate. These results are in confliction with some earlier assignmnents of the absolute configuration in the isodaucane group of sesquiterpenes.

  DOI：

  10.1021/jo00046a018

文献信息

• Lakhvich, F. A.; Khlebnikova, T. S.; Akhrem, A. A., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 12.1, p. 2280 - 2286
  作者：Lakhvich, F. A.、Khlebnikova, T. S.、Akhrem, A. A.

  DOI：——

  日期：——
• Platinum(II) cationic complexes with derivatives of 2-acyl-1,3-cyclopentanedions
  作者：T. S. Khlebnikova、I. V. Merkushin、F. A. Lakhvich

  DOI：10.1134/s107036320605001x

  日期：2006.5

  cis-Diammineplatinum(II) complexes containing 2-acyl-1,3-cyclopentadion fragments as a bidentate acido ligand were prepared by the transformation of cis-diamminediiodoplatinum(II) to cis-diamminesulfatoplatinum(II) under the action of silver sulfate with the subsequent treatment of the resulting complex by barium hydroxide and by the reaction of the synthesized base with a twofold amount of 2-acyl-1,3-cyclopentanedion. The products are the cationic complexes of cis-diammineplatinum(II) and contain 2-acyl-1,3-cyclopentanedionate as a bidentate acido ligand, which chelates platinum atom by the carbonyl groups of side acyl chain and one group connected with five-membered cycle, whereas a 2-acyl-1,3-cyclopentadion enolate anion forms counter ion.
• Preparation of fluorine-containing exo- and endocyclic enamine derivatives of 2-acylcyclopentane-1,3-diones
  作者：T. S. Khlebnikova、Yu. A. Piven’、F. A. Lakhvich

  DOI：10.1134/s1070363214030098

  日期：2014.3

  The interaction of aromatic amines (4-fluorinebenzylamine, 3-trifluoromethylbenzylamine, 4-fluoroaniline, or 3,4-difluoroaniline) with either 2-acylcyclopentane-1,3-diones (fluorine-substituted or fluorine-free) or their enol derivatives (chlorovinyldiketones) has led to fluorine-containing exo- or endocyclic enamine derivatives of 2-acylcyclopentane-1,3-diones.
• LAXVICH, F. A.;XLEBNIKOVA, T. S.;AXREM, A. A., ZH. ORGAN. XIMII, 25,(1989) N2, S. 2541-2549
  作者：LAXVICH, F. A.、XLEBNIKOVA, T. S.、AXREM, A. A.

  DOI：——

  日期：——