(+/-)-5-(2-oxocyclohexyl)pentanoic acid | 17891-23-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+/-)-5-(2-oxocyclohexyl)pentanoic acid
• 英文别名: 5-(2-Oxocyclohexyl)pentanoic acid
• CAS: 17891-23-5
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: GWGUUWYLMTZCNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 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-(2-oxocyclohexyl)pentanoic acid 在 2-萘磺酸 作用下， 以 xylene 为溶剂， 生成 螺[5.5]十一烷-5,11-二酮
  参考文献：
  名称：

  Carruthers,W.; Orridge,A., Journal of the Chemical Society. Perkin transactions I, 1977, p. 2411 - 2416

  摘要：

  DOI：
• 作为产物：
  描述：

  环己酮 、 4-戊烯酸 在 二叔丁基过氧化物 作用下， 反应 1.0h， 以62%的产率得到(+/-)-5-(2-oxocyclohexyl)pentanoic acid
  参考文献：
  名称：

  Synthesis of 2-(?'-carboxyalkyl)cycloalkanones

  摘要：

  DOI：

  10.1007/bf00957525

文献信息

• Preparation of Cyclic .ALPHA.-Hydroxy Ketones from .DELTA.- and .EPSILON.-Keto Acids Induced by the Generation of a Novel Acyl Anion Equivalent from the Carboxyl Group.
  作者：Hatsuo MAEDA、Haruka ASHIE、Toshihide MAKI、Hidenobu OHMORI

  DOI：10.1248/cpb.45.1729

  日期：——

  An improved method for the transformation of keto acids into cyclic α-hydroxy ketones, induced by the electrochemical generation of a novel acyl anion equivalent from the carboxy group, has been developed. Both five- and six-membered rings were constructed by constant-current electrolysis of δ- and ε-keto acids in the presence of Bu3P using an undivided cell equipped with a graphite anode and a Pt cathode. Attempts to prepare four- and seven-membered ring carbocycles were unsuccessful. The electrochemical reaction was found to be highly stereoselective when cyclization took place onto cyclopentanone and substituted cyclohexanone rings. Stereochemical aspects of the formation of bicyclic products, especially those having a bicyclo[4.3.0]skeleton, are discussed.

  开发了一种改进的方法，通过电化学生成从羧基衍生出的新型酰基阴离子等价物，诱导将酮酸转化为环状α-羟基酮。通过在配有石墨阳极和铂阴极的无隔膜电池中，在Bu3P存在下对δ-和ε-酮酸进行恒流电解，构建了五元和六元环。尝试制备四元和七元环碳环未能成功。当环化反应发生在环戊酮和取代环己酮环上时，发现该电化学反应具有高度立体选择性。讨论了双环产物形成的立体化学方面，特别是具有双环[4.3.0]骨架的产物。
• Organic reactions with polyphosphoric acid—VIII
  作者：S.B. Kulkarni、Sukh Dev

  DOI：10.1016/0040-4020(68)88004-4

  日期：——

  Intramolecular acylation with lactones in polyphosphoric acid has been extended to γ- and δ-lactones with angular methyls. It is further shown that hydroxy acids can conveniently replace the corresponding lactones in such reactions. The reaction has also been applied to simple esters.

  多磷酸中内酯的分子内酰化作用已扩展为具有角甲基的γ-和δ-内酯。进一步表明，在这种反应中，羟基酸可以方便地代替相应的内酯。该反应也已经应用于简单的酯。
• Synthesis and resolution of the enantiomeric trans,trans-spiro[5.5]undecane-1,7-diols and determination of their absolute configuration; (S)-(−)-spiro[5.5]undecane-1,7-dione
  作者：Rüdiger Brünner、Hans Gerlach

  DOI：10.1016/0957-4166(94)80132-0

  日期：1994.8

  and 4) with cis,cis-, cis,trans- and trans,trans-configuration are described. The structure of the lactone side product (±)-5 was elucidated by NMR spectroscopy. Resolution of the trans,trans-diol (±)-4 was accomplished via the diastereomeric (1S,4R)-camphanoates (−)-6 and (+)-7 to give (−)-4 and (+)-4. Oxidation of (−)-4 by the method of Swern yielded the optically active dione (−)-1. An X-ray crystal

  螺的合成[5.5]十一烷-1,7-二酮（1）和三个非对映体螺[5.5]十一烷-1,7-二醇（2，3和4）配有顺，顺- ，顺式，反式-和反式描述了-trans- configuration。通过NMR光谱阐明了内酯副产物（±）-5的结构。反式，反式-二醇（±）-4的拆分是通过非对映异构体（1 S，4 R）-樟脑酸酯（-）- 6和（+）- 7完成的，得到（-）- 4和（+）- 4。（-）- 4的氧化通过Swern方法得到旋光二酮（-）- 1。（-）- 6的X射线晶体结构允许分配（1 R，6 S，7 R）-（-）- 4的绝对构型，因此可以分配（S）-（-）- 1的绝对构型。衍生自（-）- 4的双（4-溴苯甲酸酯）（-）- 8的手性也证明了（1 R，6 S，7 R）-构型。
• Bicyclic- and Tricyclic-β-lactones via Organonucleophile-Promoted Bis-Cyclizations of Keto Acids:  Enantioselective Synthesis of (+)-Dihydroplakevulin
  作者：Huda Henry-Riyad、Changsuk Lee、Vikram C. Purohit、Daniel Romo

  DOI：10.1021/ol061816t

  日期：2006.9

  A highly diastereoselective, nucleophile-promoted bis-cyclization process, employing readily available and tractable keto acid substrates, is described. This methodology provides concise access to bicyclic- and tricyclic-beta-lactones bearing tertiary carbinol centers and quaternary carbons, greatly extending the scope of previous routes to bicyclic-beta-lactones from aldehyde acid substrates. The utility of the method was demonstrated by application to an enantioselective synthesis of (+)-dihydroplakevulin A. This and related processes may be revealing a subtle interplay between [2+2] cycloaddition and nucleophile-catalyzed aldol lactonization (NCAL) reaction manifolds.
• STAROSTIN E. K.; ALEKSANDROV A. V.; NIKISHIN G. I., IZV. AN CCCP. CEP. XIM.,(1986) N 10, 2260-2262
  作者：STAROSTIN E. K.、 ALEKSANDROV A. V.、 NIKISHIN G. I.

  DOI：——

  日期：——