(6-甲酰基环己-2-烯-1-基)乙酸酯 | 61088-60-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (6-甲酰基环己-2-烯-1-基)乙酸酯
• 英文名称: 6-formyl-2-cyclohexenyl acetate
• 英文别名: (1R,2S)-Acetic acid 6-formyl-cyclohex-2-enyl ester；6-Formylcyclohex-2-en-1-yl acetate；(6-formylcyclohex-2-en-1-yl) acetate
• CAS: 61088-60-6
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: SSIZYDVAXPXFAA-UHFFFAOYSA-N

物化性质

• 沸点：
  235.7±40.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  (6-甲酰基环己-2-烯-1-基)乙酸酯 在 sodium iodide 作用下， 以 六甲基磷酰三胺 为溶剂， 生成 methyl (Z)-2-benzenesulfonyl-4-(2'-acetoxy-3'-cyclohexen-1'-yl)butanoate
  参考文献：
  名称：

  Cyclizations via organopalladium intermediates. Macrolide formation

  摘要：

  DOI：

  10.1021/ja00453a070
• 作为产物：
  描述：

  1-乙酰氧基-1,3-丁二烯 、 丙烯醛 在 (5S)-(-)-2,2,3-trimethyl-5-benzyl-4-imidazolidinone monohydrochloride 作用下， 以 水 为溶剂， 以87%的产率得到(6-甲酰基环己-2-烯-1-基)乙酸酯
  参考文献：
  名称：

  A sustainable procedure for highly enantioselective organocatalyzed Diels–Alder cycloadditions in homogeneous ionic liquid/water phase

  摘要：

  The MacMillan iminium catalyst was investigated for asymmetric Diels-Alder cycloadditions in ionic liquid/H(2)O homogeneous phase. Superior selectivity, product yield, and shorter reaction times were observed in comparison with classical organic solvents. Additional advantages are the easy synthetic procedure, the excellent recovery of products, and the recyclability of the whole system. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.014

文献信息

• Synthesis of Main-Chain Ionic Polymers of Chiral Imidazolidinone Organocatalysts and Their Application to Asymmetric Diels-Alder Reactions
  作者：Naoki Haraguchi、Nagisa Takenaka、Aisyah Najwa、Yuta Takahara、Mah Kar Mun、Shinichi Itsuno

  DOI：10.1002/adsc.201701016

  日期：2018.1.4

  Main‐chain ionic polymers incorporating chiral imidazolidinone moieties in the polymer main chain were successfully synthesized by the polyaddition reaction of a chiral imidazolidinone dimer with a disulfonic acid. The organocatalytic activities of these polymers were investigated in the asymmetric Diels–Alder reaction between trans‐cinnamaldehyde and 1,3‐cyclopentadiene. The catalytic performance

  通过手性咪唑烷酮二聚体与二磺酸的加聚反应，成功合成了在聚合物主链中包含手性咪唑烷酮部分的主链离子聚合物。在反式肉桂醛和1,3-环戊二烯之间的不对称Diels-Alder反应中研究了这些聚合物的有机催化活性。发现聚合物的催化性能对二磺酸酯单元和咪唑烷酮二聚体的化学结构敏感。使用这些非均相聚合手性有机催化剂，对内的对映选择性高达99％获得异构体。该结果高于在均相溶液中用相应的单体和二聚体对应物获得的结果。回收聚合物手性有机催化剂并重复使用数次，以保持其高对映选择性。
• Chemical transformation of substrates using nonmetallic, organic catalyst compositions
  申请人：The Regents of the Univerisity of California

  公开号：US06369243B1

  公开（公告）日：2002-04-09

  A method is provided for catalytically transforming a functional group within a first reactant by reaction with a second reactant in the presence of a nonmetallic, organic catalyst composition composed of a heteroatom-containing activator and an acid, or a salt of a heteroatom-containing activator and an acid. Exemplary first reactants are &agr;,&bgr;-unsaturated carbonyl compounds such as &agr;,&bgr;-unsaturated ketones and &agr;,&bgr;-unsaturated aldehydes. The heteroatom of the activator is a Group 15 or Group 16 element such as nitrogen, oxygen, sulfur or phosphorus, and exemplary heteroatom-containing activators are amines. Chiral heteroatom-containing activators can be used to catalyze enantioselective reactions, such that a chiral product is obtained from a chiral or achiral starting material in enantiomerically pure form.

  提供了一种方法，通过在非金属有机催化剂组合物的存在下，使第一反应物中的一个官能团与第二反应物发生反应，从而催化转化它。该催化剂组合物由含杂原子的活化剂和酸组成，或者由含杂原子的活化剂和酸的盐组成。示例第一反应物是α,β-不饱和羰基化合物，如α,β-不饱和酮和α,β-不饱和醛。活化剂的杂原子是第15组或第16组元素，如氮、氧、硫或磷，示例含杂原子的活化剂是胺。手性含杂原子的活化剂可用于催化对映选择性反应，从而从手性或不手性的起始物质中获得对映纯形式的手性产物。
• Molybdenum catalysts for allylic alkylation
  作者：Barry M. Trost、Mark Lautens

  DOI：10.1021/ja00384a071

  日期：1982.10

  This paper reports on the stoichiometric and catalytic allylic substituion reactions involving molybdenum complexes and the sensitivity of regioselectivity toward the nature of the ligands on molybdenum. Results indicated that the allylic alkylation catalyzed by molybdenum forms a useful and frequently complementary alternative to the palladium-catalyzed reaction. For example, regioselectivity appears

  本文报道了涉及钼配合物的化学计量和催化烯丙基取代反应以及区域选择性对钼配体性质的敏感性。结果表明，由钼催化的烯丙基烷基化形成了钯催化反应的有用且经常互补的替代方案。例如，在 Mo 的情况下，区域选择性似乎对配体变化更敏感。在 ..pi..-allyl 片段的一级碳和二级碳上的连接选择性更高。存在。另一方面，这些反应需要更高的温度和更长的时间。需要对这种钼化学进行更彻底的评估，以描绘其全部潜力。
• Efficient Organocatalyst Supported on a Simple Ionic Liquid as a Recoverable System for the Asymmetric Diels-Alder Reaction in the Presence of Water
  作者：Antonio De Nino、Loredana Maiuolo、Pedro Merino、Monica Nardi、Antonio Procopio、David Roca-López、Beatrice Russo、Vincenzo Algieri

  DOI：10.1002/cctc.201402973

  日期：2015.3

  investigated. The Diels–Alder reactions of several dienes and dienophiles proceeded efficiently in the presence of the catalyst to provide the desired products in moderate to good yields and from good to excellent enantioselectivities. The conformation study confirms that in the transition state the Re face is shielded completely by the phenyl ring and an approach on the less hindered Si face is preferred. Particularly

  新型高效有机催化剂，即（5 S）-2,2,2,3-三甲基-5-硫代苄基甲基-4-咪唑啉酮盐酸盐的合成，表征和评估已经完成。催化剂具有重要的结构特征，应增加催化效率和在极性介质中的溶解度。研究了离子液体负载的咪唑烷酮催化剂在对映选择性Diels-Alder反应中的应用。在催化剂的存在下，几种二烯和亲二烯体的狄尔斯-阿尔德反应有效地进行，以中等至良好的收率和良好的至优异的对映选择性提供了所需的产物。构象研究证实，在过渡状态下，Re表面被苯环完全屏蔽，最好采用受阻较小的Si表面。特别引人注目的是，整个离子液体/ HCl 0.01  M /催化剂体系可以回收并重复使用多达六次，而不会明显降低催化活性。
• Acid addition salts of imidazolidinones as reaction catalysts
  申请人：The Regents of the University of California

  公开号：US06307057B1

  公开（公告）日：2001-10-23

  Acid addition salts of imidazolidinones are provided as catalysts for transforming a functional group within a first reactant by reaction with a second reactant. Exemplary first reactants are &agr;,&bgr;-unsaturated carbonyl compounds such as &agr;,&bgr;-unsaturated ketones and &agr;,&bgr;-unsaturated aldehydes. Chiral imidazolidinone salts can be used to catalyze enantioselective reactions, such that a chiral product is obtained from a chiral or achiral starting material in enantiomerically pure form.

  本发明提供了咪唑啉酮的酸加成盐作为催化剂，通过与第二个反应物反应来转化第一个反应物中的功能基团。典型的第一个反应物是α，β-不饱和羰基化合物，如α，β-不饱和酮和α，β-不饱和醛。手性咪唑啉酮盐可用于催化对映选择性反应，从手性或消旋起始物质中获得手性产物的对映纯形式。