5-tert-butyl-2-oxocyclohexanecarboxylic acid | 42031-70-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5-tert-butyl-2-oxocyclohexanecarboxylic acid
• 英文别名: 5-tert.-Butyl-cyclohexan-2-on-1-carbonsaeure；2-Carboxy-4-tert.butylcyclohexanon；5-tert-butyl-2-oxocyclohexane-1-carboxylic acid
• CAS: 42031-70-9
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: XIFTXKJKXFSKAS-UHFFFAOYSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  328.7±35.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-tert-butyl-2-oxocyclohexanecarboxylic acid 在 氢氧化钾 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 xylene 为溶剂， 反应 16.0h， 生成 methyl cis-5-tert-butyl-1-methyl-2-oxocyclohexanecarboxylate
  参考文献：
  名称：

  Kinetics of decarboxylation of the two epimers of 5-tert-butyl-1-methyl-2-oxocyclohexanecarboxlic acid: lack of stereoelectronic control in .beta.-keto acid decarboxylation

  摘要：

  DOI：

  10.1021/jo00172a011
• 作为产物：
  描述：

  二氧化碳 、 4-叔丁基环己酮 在 正丁基锂 、 1,10-菲罗啉 、 二异丙胺 作用下， 生成 5-tert-butyl-2-oxocyclohexanecarboxylic acid
  参考文献：
  名称：

  Kinetics of decarboxylation of the two epimers of 5-tert-butyl-1-methyl-2-oxocyclohexanecarboxlic acid: lack of stereoelectronic control in .beta.-keto acid decarboxylation

  摘要：

  DOI：

  10.1021/jo00172a011

文献信息

• Substrate scope in the copper-mediated construction of bis-oxindoles via a double C–H/Ar–H coupling process
  作者：Pauline Drouhin、Timothy E. Hurst、Adrian C. Whitwood、Richard J.K. Taylor

  DOI：10.1016/j.tet.2015.02.060

  日期：2015.9

  The synthesis of bis-oxindoles via the copper(II)-mediated double cyclisation of linear bis-anilides is described. Cu(OAc)(2)center dot H2O was identified as an efficient and inexpensive catalyst for this process. In contrast to previous methods, which rely on the synthesis of the central core from existing oxindole building blocks, this new approach focusses on concurrent formation of both oxindole rings from a simple linear precursor, allowing the formation of bis-oxindoles containing a diverse range of cyclic and acyclic linkers using a single synthetic method. (C) 2015 Elsevier Ltd. All rights reserved.
• Copper-Mediated Construction of Spirocyclic Bis-oxindoles via a Double C–H, Ar–H Coupling Process
  作者：Pauline Drouhin、Timothy E. Hurst、Adrian C. Whitwood、Richard J. K. Taylor

  DOI：10.1021/ol5024129

  日期：2014.9.19

  A double C-H, Ar-H coupling process for the conversion of bis-anilides into spirocyclic bis-oxindoles, enabling the concomitant formation of two all-carbon quaternary centers at oxindole 3-positions in a diastereoselective manner, is described. The optimum cyclization conditions utilize stoichiometric Cu(OAc)(2).H2O/KOtBu in DMF at 110 degrees C and have been applied to prepare a range of structurally diverse bis-spirooxindoles in fair to good yields (28-77%); the method has also been extended to prepare bis-oxindoles linked by a functionalized acyclic carbon chain.
• KAYSER, R. H.;BRAULT, M.;POLLACK, R. M.;BANTIA, S.;SADOFF, S. F., J. ORG. CHEM., 1983, 48, N 24, 4497-4502
  作者：KAYSER, R. H.、BRAULT, M.、POLLACK, R. M.、BANTIA, S.、SADOFF, S. F.

  DOI：——

  日期：——
• Kinetics of decarboxylation of the two epimers of 5-tert-butyl-1-methyl-2-oxocyclohexanecarboxlic acid: lack of stereoelectronic control in .beta.-keto acid decarboxylation
  作者：Robert H. Kayser、Margaret Brault、Ralph M. Pollack、Shanta Bantia、Scott F. Sadoff

  DOI：10.1021/jo00172a011

  日期：1983.12