ethyl 3,3-dimethyl-6-oxocyclohex-1-enecarboxylate | 1258209-05-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,3-dimethyl-6-oxocyclohex-1-enecarboxylate
• 英文别名: Ethyl 3,3-dimethyl-6-oxocyclohexene-1-carboxylate
• CAS: 1258209-05-0
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: CKPZSGYOJUUUMX-UHFFFAOYSA-N

物化性质

• 沸点：
  285.5±39.0 °C(Predicted)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  ethyl 3,3-dimethyl-6-oxocyclohex-1-enecarboxylate 在 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydride 、 S-4,5-二氢-2-(2-((S)-4,5-二氢-4-异丙基噁唑-2-基)丙-2-基)-4-异丙基噁唑 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 生成 (S)-ethyl 2-((diphenoxyphosphoryl)oxy)-5,5-dimethyl-6-((R)-5-oxo-2,5-dihydrofuran-2-yl)cyclohex-1-enecarboxylate
  参考文献：
  名称：

  Catalytic Enantioselective Vinylogous Mukaiyama–Michael Addition of 2-Silyloxyfurans to Cyclic Unsaturated Oxo Esters

  摘要：

  The copper-catalyzed asymmetric addition of 2-silyloxyfurans to cyclic unsaturated oxo esters is reported. The reaction proceeds with excellent diastereocontrol (usually dr 99:1) and modest to high enantioselectivity, depending on the nature of the ester group and the substitution of the cyclic oxo ester. We have shown that these substrates can be transformed into a variety of building blocks bearing a gamma-butenolide or gamma-lactone connected to a cycloalkane or cycoalkene moiety.

  DOI：

  10.1021/jo3020648

文献信息

• Vinylogous Mukaiyama-Michael Reactions between 2-Silyloxyfurans and Cyclic Enones or Unsaturated Oxo Esters
  作者：Laurent Chabaud、Thierry Jousseaume、Pascal Retailleau、Catherine Guillou

  DOI：10.1002/ejoc.201000504

  日期：——

  Lewis acid catalyzed vinylogous Mukaiyama–Michael (VMM) reactions between 2-(trialkylsilyloxy)furans 1 and α,β-unsaturated cyclic enones 2 or oxo esters 4 have been investigated. Both substrates proved to be useful Michael acceptors in the title reaction, giving the butenolides 3 and 5 in good yields. A comparative study between the α,β-unsaturated cyclic enones 2 and the oxo esters 4 as Michael acceptors

  已经研究了路易斯酸催化的 2-(三烷基甲硅烷氧基)呋喃 1 和 α,β-不饱和环烯酮 2 或氧代酯 4 之间的乙烯基 Mukaiyama-Michael (VMM) 反应。两种底物都证明是标题反应中有用的迈克尔受体，以良好的产率得到丁烯内酯 3 和 5。作为迈克尔受体的 α,β-不饱和环状烯酮 2 和氧代酯 4 之间的比较研究表明，后一类化合物具有更好的非对映控制。在这两个系列中，主要异构体的晶体结构揭示了新形成的立体中心的反关系。从这些数据中，可以提出两种类型的过渡状态：具有反周向取向的开放 TS 或具有 exo 方法的类 Diels-Alder TS。
• CYCLOALKENE DERIVATIVES, PROCESS FOR PRODUCING THE SAME, AND USE
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1063228A1

  公开（公告）日：2000-12-27

  Compounds represented by formula (1a) or salts thereof, which are preventives/remedies for heart diseases, autoimmune diseases, inflammatory diseases, septic shock, etc., wherein R represents an optionally substituted aliphatic hydrocarbon group, optionally substituted aromatic hydrocarbon group, optionally substituted heterocyclic group, group represented by OR1 (wherein R1 represents hydrogen or an optionally substituted aliphatic hydrocarbon group), or group represented by formula (A) (wherein R1b band R1c are the same or different and each represents hydrogen or an optionally substituted aliphatic hydrocarbon group); R0 represents hydrogen or an aliphatic hydrocarbon group, or R and R0 in combination represent a bond; Ar represents an optionally substituted aromatic hydrocarbon group; and (B) or (C) where n is an integer of 1 to 4.

  式(1a)代表的化合物或其盐，可预防/治疗心脏病、自身免疫性疾病、炎症性疾病、脓毒性休克等、其中 R 代表任选取代的脂肪族烃基、任选取代的芳香族烃基、任选取代的杂环基、由 OR1 代表的基团（其中 R1 代表氢或任选取代的脂肪族烃基）或由式（A）代表的基团（其中 R1b 带 R1c 相同或不同，且各自代表氢或任选取代的脂肪族烃基）；R0 代表氢或脂族烃基，或 R 和 R0 结合代表键； Ar 代表任选取代的芳族烃基；以及 (B) 或 (C) 其中 n 为 1 至 4 的整数。
• prodrugs containing cycloalkene derivatives
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1524263A1

  公开（公告）日：2005-04-20

  The present invention provides a prodrug of a compound represented by the formula: wherein R represents an aliphatic hydrocarbon group optionally having substituents, an aromatic hydrocarbon group optionally having substituents, a heterocyclic group optionally having substituents, a group represented by the formula: OR1 (wherein R1 represents a hydrogen atom or an aliphatic hydrocarbon group optionally having substituents) or a group represented by the formula: wherein R1b represents a hydrogen atom or an aliphatic hydrocarbon group optionally having substituents, R1c is, same with or different from R1b, a hydrogen atom or an aliphatic hydrocarbon group optionally having substituents, R0 represents a hydrogen atom or an aliphatic hydrocarbon group, or R and R0 represents a bond with each other, Ar represents an aromatic hydrocarbon group optionally having substituents, and n is an integer of 1 to 4, or a salt thereof, which is a agent for preventing or treating diseases such as cardiac disease, autoimmune disease, septick shock, etc..

  本发明提供了一种由式表示的化合物的原药： 其中 R 代表任选具有取代基的脂族烃基、任选具有取代基的芳族烃 基、任选具有取代基的杂环基、由式表示的基团：OR1（其中 R1 代表氢原子或任选具有取代基的脂族烃基）或由式表示的基团： 其中 R1b 代表氢原子或任选具有取代基的脂族烃基；R1c 与 R1b 相同或不同，是氢原子或任选具有取代基的脂族烃基；R0 代表氢原子或脂族烃基；或 R 和 R0 互为键；Ar 代表任选具有取代基的芳香族烃基、 和 n 是 1 至 4 的整数，或其盐，可用于预防或治疗疾病，如心脏病、自身免疫性疾病、败血症休克等。
• US6495604B1
  申请人：——

  公开号：US6495604B1

  公开（公告）日：2002-12-17
• Catalytic Enantioselective Vinylogous Mukaiyama–Michael Addition of 2-Silyloxyfurans to Cyclic Unsaturated Oxo Esters
  作者：Xavier Jusseau、Pascal Retailleau、Laurent Chabaud、Catherine Guillou

  DOI：10.1021/jo3020648

  日期：2013.3.15

  The copper-catalyzed asymmetric addition of 2-silyloxyfurans to cyclic unsaturated oxo esters is reported. The reaction proceeds with excellent diastereocontrol (usually dr 99:1) and modest to high enantioselectivity, depending on the nature of the ester group and the substitution of the cyclic oxo ester. We have shown that these substrates can be transformed into a variety of building blocks bearing a gamma-butenolide or gamma-lactone connected to a cycloalkane or cycoalkene moiety.