trans-1-Acetyl-2-(2-propenyl)cyclopentane | 65682-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-1-Acetyl-2-(2-propenyl)cyclopentane
• 英文别名: trans-1-acetyl-2-allyl-cyclopentane；1-[(1R,2S)-2-prop-2-enylcyclopentyl]ethanone
• CAS: 65682-09-9；65682-10-2；85283-32-5
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: KQJMZWRJJQBLOR-ZJUUUORDSA-N

物化性质

• 沸点：
  209.8±9.0 °C(Predicted)
• 密度：
  0.900±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  trans-1-Acetyl-2-(2-propenyl)cyclopentane 在 三丁基膦 、 triphenylmethylium hexachloroantimonate(V) 、 碳酸氢钠 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Neighboring group participation in Lewis acid-promoted [3 + 4] and [3 + 5] annulations. The stereocontrolled synthesis of tricyclic ethers

  摘要：

  A variety of 1,4- and 1,5-keto aldehydes derived from cycloalkanes are coupled with the bis(trimethylsilyl) enol ether of methyl acetoacetate in the presence of either TMSOTf or TrSbCl6 to generate tricyclic ethers. The reactions proceed with excellent regiochemical control by a mechanism involving neighboring group participation. This mechanism involves initial formation of a bicyclic oxocarbenium ion intermediate from the keto aldehyde substrates. The geometries of selected bicyclic intermediates have been optimized using the AM1 method allowing successful prediction of the stereochemical outcomes in the cyclization in most cases. Epimerization of alpha-chiral keto aldehyde substrates does not appear to occur in these Lewis acid-promoted annulation reactions.

  DOI：

  10.1021/jo00074a018
• 作为产物：
  描述：

  1-[(1R,2S)-2-(2-bromoprop-2-enyl)cyclopentyl]ethanone 以48%的产率得到
  参考文献：
  名称：

  TROST, B. M.;COPPOLA, B. P., J. AMER. CHEM. SOC., 1982, 104, N 24, 6879-6881

  摘要：

  DOI：

文献信息

• Stereoselective Photochemical Synthesis and Structure Elucidation of 1-Methyl-Substituted Tricyclo[6.2.0.02,6]decanes and Tricyclo[7.2.0.02,7]undecanes
  作者：Thorsten Bach、Anja Spiegel

  DOI：10.1002/1099-0690(200202)2002:4<645::aid-ejoc645>3.0.co;2-a

  日期：2002.2

  The trans- and cis-substituted 2-allyl-1-(2-propenyl)cyclopentanes 5a (47% yield) and 5b (33% yield) as well as the trans- and cis-substituted 2-allyl-1-(2-propenyl)cyclohexanes 6a (48% yield) and 6b (64% yield) were synthesized from the corresponding 1-acetyl-1-cycloalkenes. Their intramolecular, Cu-catalyzed [2+2] photocycloaddition reaction was studied in ether as the solvent. The reaction proceeded

  反式和顺式取代的 2-烯丙基-1-（2-丙烯基）环戊烷 5a（产率 47%）和 5b（产率 33%）以及反式和顺式取代的 2-烯丙基-1-(2 -丙烯基）环己烷6a（48%产率）和6b（64%产率）由相应的1-乙酰基-1-环烯烃合成。在醚作为溶剂中研究了它们的分子内、Cu 催化的 [2+2] 光环加成反应。该反应以优异的表面非对映选择性进行。反式环烷烃 5a 和 6a 仅产生反式反顺式产物 11a (80%) 和 12a (80%)，而顺式环烷烃 5b 和 6b 产生顺式-顺式-顺式产物 11b (77%) 和12b (88%)。产物11a和12a的结构通过核磁共振光谱阐明。化合物 11b 和 12b 的构型分配通过这些化合物的独立合成得到证实。
• Rhodium-Catalyzed Intramolecular Cyclopropanation of α-Diazo β-Keto Nitriles Containing an Unsaturated Substituted Cycloalkyl Group
  作者：Jia-Liang Zhu、Yung-Peng Wu

  DOI：10.1055/s-0036-1588174

  日期：2017.7

  α-diazo β-keto nitriles bearing trans-2-allyl-, -vinyl-, or -phenylcycloalkyl groups were prepared and their intramolecular cyclopropanation reactions were examined. In the presence of Rh2(OAc)4 (1 mol%) as a catalyst, the allyl- and vinyl-substituted precursors were found to undergo cyclopropanation smoothly at ambient temperature to afford novel tricyclic α-keto cyclopropyl nitriles in 47–88% yields

  制备了几种带有反式-2-烯丙基-、-乙烯基-或-苯基环烷基的α-重氮β-酮腈，并研究了它们的分子内环丙烷化反应。在 Rh2(OAc)4 (1 mol%) 作为催化剂存在下，发现烯丙基和乙烯基取代的前体在环境温度下顺利进行环丙烷化，以 47-88% 的产率提供新型三环 α-酮基环丙基腈非对映体比例范围为 79:21 至 >99:1。另一方面，含苯基类似物的催化反应没有产生任何环丙基产物，而是以定量产率提供官能化的六氢菲或四氢环戊萘衍生物。
• Conjugate addition of allylsilanes to α,β-enones. Obtention of cyclobutyl derivatives
  作者：Roselyne Pardo、Jean-Pierre Zahra、Maurice Santelli

  DOI：10.1016/s0040-4039(01)86648-x

  日期：1979.1