(1R*,2R*)-ethyl 2-acetyl-4,5-dimethylcyclohex-4-enecarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (1R*,2R*)-ethyl 2-acetyl-4,5-dimethylcyclohex-4-enecarboxylate
• 英文别名: ethyl (1R,6R)-6-acetyl-3,4-dimethylcyclohex-3-ene-1-carboxylate
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: PAHFSQQVZIXKTN-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-4-氧代-2-戊烯酸乙酯 、 2,3-二甲基-1,3-丁二烯 在 三氯化铝 作用下， 以75%的产率得到(1R*,2R*)-ethyl 2-acetyl-4,5-dimethylcyclohex-4-enecarboxylate
  参考文献：
  名称：

  Sequenced Reactions with Samarium(II) Iodide. Sequential Intermolecular Carbonyl Addition/Intramolecular Nucleophilic Acyl Substitution for the Preparation of Seven-, Eight-, and Nine-Membered Carbocycles

  摘要：

  Samarium(II) iodide has been employed to promote a tandem intermolecular carbonyl addition/intramolecular nucleophilic acyl substitution sequence, generating seven- through nine-membered monocyclic, bicyclic, and tricyclic ring systems with good yields and high diastereoselectivities. This tandem reaction consists of an intermolecular reaction followed by an intramolecular ring expansion that results in a formal [m + n] cycloaddition, starting from extremely simple, readily available substrates. The regioselectivity and stereoselectivity of the process arise from a tuning of the reducing power of samarium(II) iodide with nickel(II) iodide in the first step and irradiation with visible light in the second. By using this method, a variety of structural motifs have been assembled rapidly in good yields.

  DOI：

  10.1021/jo980119e

文献信息

• Efficient oxidation-Wittig olefination-Diels–Alder multicomponent reactions of α-hydroxyketones
  作者：Geraint H. Harris、Andrew E. Graham

  DOI：10.1016/j.tetlet.2010.10.121

  日期：2010.12

  alpha-Hydroxyketones undergo efficient tandem oxidation-Wittig olefination reactions in the presence of an oxidant to produce high yields of gamma-ketocrotonate products. On carrying out the oxidation-Wittig olefination reaction in the presence of 2,3-dimethyl-1,3-butadiene, a novel multicomponent reaction sequence provides access to cycloadducts in high yield. (C) 2010 Elsevier Ltd. All rights reserved.
• Sequenced Reactions with Samarium(II) Iodide. Sequential Intermolecular Carbonyl Addition/Intramolecular Nucleophilic Acyl Substitution for the Preparation of Seven-, Eight-, and Nine-Membered Carbocycles
  作者：Gary A. Molander、Cristina Alonso-Alija

  DOI：10.1021/jo980119e

  日期：1998.6.1

  Samarium(II) iodide has been employed to promote a tandem intermolecular carbonyl addition/intramolecular nucleophilic acyl substitution sequence, generating seven- through nine-membered monocyclic, bicyclic, and tricyclic ring systems with good yields and high diastereoselectivities. This tandem reaction consists of an intermolecular reaction followed by an intramolecular ring expansion that results in a formal [m + n] cycloaddition, starting from extremely simple, readily available substrates. The regioselectivity and stereoselectivity of the process arise from a tuning of the reducing power of samarium(II) iodide with nickel(II) iodide in the first step and irradiation with visible light in the second. By using this method, a variety of structural motifs have been assembled rapidly in good yields.