1-乙基-3,5-二甲氧基环己-2,5-二烯-1-羧酸 | 108864-34-2

• 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: 1-乙基-3,5-二甲氧基环己-2,5-二烯-1-羧酸
• 英文名称: 1-ethyl-3,5-dimethoxycyclohexa-2,5-dienecarboxylic acid
• 英文别名: 2,5-Cyclohexadiene-1-carboxylic acid, 1-ethyl-3,5-dimethoxy-；1-ethyl-3,5-dimethoxycyclohexa-2,5-diene-1-carboxylic acid
• CAS: 108864-34-2
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: ZZLGGYURSXODIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-乙基-3,5-二甲氧基环己-2,5-二烯-1-羧酸 在 lead(IV) tetraacetate 作用下， 以 苯 为溶剂， 以94%的产率得到1,3-dimethoxy-5-ethylbenzene
  参考文献：
  名称：

  Chiloglottones的合成–具有欺骗性的兰花及其授粉媒介的化学信息素†

  摘要：

  通过一个顺序描述了单烷基和2,5-二烷基-1,3-环己二酮（1）的五步合成过程，该过程涉及从容易获得且廉价的起始原料进行连续的桦木还原和烷基化，3,5-二甲氧基苯甲酸。考虑了两种方法，其中在C-2处的烷基化发生在所提出的还原之前或之后。一种成功的方法，其中3-烷基间苯二酚衍生物（3）的桦木还原在烷基化之前进行，已成功用于合成Chiloglottone 1（1dc），总收率为58％。Chiloglottone 1是一类新的天然产物的成员，代表了澳大利亚性欺骗性兰花属Chiloglottis中的一种已知的胸腺黄蜂新性紫斑狼疮性信息素和传粉媒介引诱剂。通过电造影检查评估合成的同系物的生物活性。

  DOI：

  10.1039/b912233h
• 作为产物：
  描述：

  3,5-二甲氧基苯甲酸 以50%的产率得到
  参考文献：
  名称：

  CASARES A.; CARDOSO J. M. L.; MALDONADO L. A., SYNTH. COMMUN., 1981, 11, NO 3, 223-229

  摘要：

  DOI：

文献信息

• Solid-Supported Cyclohexane-1,3-dione (CHD):  A “Capture and Release” Reagent for the Synthesis of Amides and Novel Scavenger Resin
  作者：Cara E. Humphrey、Morag A. M. Easson、Jason P. Tierney、Nicholas J. Turner

  DOI：10.1021/ol027503p

  日期：2003.3.1

  [reaction: see text] A three-step synthesis of cyclohexane-1,3-dione (CHD) resin 6 on polystyrene resin is described. Resin 6 was used to prepare an amide library of high purity by microwave-assisted serial "capture and release" and can be recycled for this purpose. High-loading CHD resin 10 was also shown to scavenge allyl cations in solution.

  [反应：参见正文]描述了在聚苯乙烯树脂上的三步合成环己烷-1,3-二酮（CHD）树脂6。树脂6用于通过微波辅助系列“捕获和释放”制备高纯度的酰胺库，并且可以为此目的进行回收。高负荷的CHD树脂10也显示出清除溶液中的烯丙基阳离子。
• The Birch Reduction - Dialkylation Reaction of Aromatic Carboxylic Acids. Identification of NaNH₂as the Base Responsible for the Second Alkylation
  作者：J. A. Guzmán、R. Castanedo、L. A. Maldonado

  DOI：10.1080/00397919108019789

  日期：1991.4

  Abstract The Birch reduction-alkylation of 3,5-dimethoxybenzoic acid with excesses Na and EtBr gives 1,4-diethyl-3,5-dimethoxy-2, 5-cyclohexadiene carboxylic acid, 3. The responsible for the alkylation at C-4 has been identified as NaNH2, generated in Situ.

  摘要 3,5-二甲氧基苯甲酸与过量 Na 和 EtBr 的 Birch 还原烷基化得到 1,4-二乙基-3,5-二甲氧基-2, 5-环己二烯羧酸，3。负责在 C-4 处烷基化已被鉴定为原位生成的 NaNH2。
• Cyclohexane-1,3-dione derivatives having a herbicidal activity
  申请人：Dunlena Pty. Limited

  公开号：EP0219343A2

  公开（公告）日：1987-04-22

  Compounds of the formula (2), including all isomeric and/ or tautomeric forms. where X is 0 or NR6, R' is an organic group, hydrogen or an inorganic cation, R2 to R6 are independently organic groups or hydrogen are disclosed. The presence of the group R5 gives improved herbicidal properties. R5 is selected from the group consisting of: allyl; substituted alkyl wherein the alkyl group is substituted with a substituent selected from the group consisting of alkoxy, alkylthio, optionally substituted phenyl, and optionally substituted heterocycle; or COXR4 and R5 together with the carbon to which they are attached form a substituted or unsubstituted 5- or 6- membered heterocyclic ring. The spirocyclic compounds are preferred. The synthesis of the compounds, and herbicidal (including plant growth regulating) uses and compositions, are disclosed.

  式（2）化合物，包括所有异构体和/或同分异构体形式。 其中 X 为 0 或 NR6，R'为有机基团、氢或无机阳离子，R2 至 R6 独立地为有机基团或氢。基团 R5 的存在提高了除草性能。 R5 选自以下组：烯丙基；取代的烷基，其中烷基被选自以下组的取代基取代：烷氧基、烷硫基、任选取代的苯基和任选取代的杂环；或 COXR4 和 R5 与它们所连接的碳一起形成一个取代或未取代的 5 或 6 位杂环。优选螺环化合物。公开了这些化合物的合成以及除草（包括植物生长调节）用途和组合物。
• Lipase-Catalyzed Kinetic Resolution on Solid-Phase via a “Capture and Release” Strategy
  作者：Cara E. Humphrey、Nicholas J. Turner、Morag A. M. Easson、Sabine L. Flitsch、Rein V. Ulijn

  DOI：10.1021/ja037922x

  日期：2003.11.1

  The lipase-catalyzed kinetic resolution of (R/S)-3-phenylbutyric acid 2 using solid-supported cyclohexane-1,3-dione (CHD) 6 is described. In each case the predominant enantiomer observed, after cleavage from the resin, was (R)-(-)-3-phenylbutyric acid (R)-2 (ee > 99%) rather than the expected (S)-enantiomer of 2. This observation is in contrast to the fact that Chromobacterium viscosum lipase shows high enantiospecificity for the (S)-enantiomer in the corresponding solution-phase hydrolysis reactions. The (R)-acyl group was subsequently released from the resin by NaOH hydrolysis, and the yield of the reaction could be improved by triple acylation of the resin.
• Liepa, Andris J.; Wilkie, John S.; Winzenberg, Kevin N., Australian Journal of Chemistry, 1989, vol. 42, # 8, p. 1217 - 1225
  作者：Liepa, Andris J.、Wilkie, John S.、Winzenberg, Kevin N.

  DOI：——

  日期：——