3-methylcyclohexanone-3-acetic acid | 119986-97-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methylcyclohexanone-3-acetic acid
• 英文别名: (1-methyl-3-oxo-cyclohexyl)-acetic acid；1-Methyl-cyclohexanon-(3)-essigsaeure-(1)；(1-Methyl-3-oxo-cyclohexyl)-essigsaeure；1-methyl-3-oxo-cyclohexaneacetic acid；<3-Oxo-1-methyl-cyclohexyl-(1)>-essigsaeure；2-(1-Methyl-3-oxocyclohexyl)acetic acid
• CAS: 119986-97-9
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: KRQDTGNRVHFLHT-UHFFFAOYSA-N

物化性质

• 熔点：
  37 °C
• 沸点：
  196 °C(Press: 15 Torr)
• 密度：
  1.108±0.06 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：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  3-methylcyclohexanone-3-acetic acid 在 36percent (w/w) PPA 作用下， 以 溶剂黄146 为溶剂， 反应 7.0h， 以80%的产率得到4-methylbicyclo[2.2.2]octane-2,6-dione
  参考文献：
  名称：

  Conformational consequences of intramolecular cyclopropanation within small bicyclic systems.

  摘要：

  DOI：

  10.1016/s0040-4039(00)80071-4
• 作为产物：
  描述：

  7-methyl-7-vinyl-1,4-dioxaspiro[4.5]decane 在 jones reagent 、 硼烷四氢呋喃络合物 作用下， 生成 3-methylcyclohexanone-3-acetic acid
  参考文献：
  名称：

  Studies directed toward the total synthesis of cerorubenic acid-III. 1. Expedient construction of the tetracyclic core by oxyanionic sigmatropy

  摘要：

  A synthesis of the ABCD ring framework of cerorubenic acid-III is described. Diketone 5 was first prepared by intramolecular oxidative coupling of the dienolate 10 and then suitably desymmetrized to deliver 15b. Anionic oxy-Cope rearrangement of this intermediate resulted in construction of 18, a ketone not only having all three contiguous stereogenic centers properly established but also equipped with adequate functionality for the further elaboration of ring D. In the present effort, this thrust took the form of homologation to 21, conversion to the activated diene 22, and Diels-Alder cycloaddition to methyl acrylate at high pressure. Once it became obvious that first-formed ketone 26 greatly preferred adoption of trans stereochemistry at the ring juncture, attempts to skirt this issue were made by preparing both 29 and 32. However, these advanced intermediates proved unresponsive to conjugate reduction, and attention was therefore redirected to alternative possible means for elaboration of the eastern sector.

  DOI：

  10.1021/jo00068a019

文献信息

• Bridged ring systems—I
  作者：R.D.H. Murray、W. Parker、R.A. Raphael

  DOI：10.1016/0040-4020(61)80056-2

  日期：1961.1

  Details are given for the synthesis of 5-methyl-1-(ketoisobutenyl) bicyclo [3:3:1] nonan-3-one (X) and its attempted conversion into a clovene precursor (XI) is described.

  给出了合成5-甲基-1-（酮异丁烯基）双环[3：3：1]壬基-3-酮（X）的细节，并描述了其试图转化为丁香前体（XI）的方法。
• INTRAMOLECULAR OXIDATIVE COUPLING OF A BISENOLATE: 4-METHYLTRICYCLO[2.2.2.03,5]OCTANE-2,6-DIONE
  作者：Poupart, Marc-André、Lassalle, Gilbert、Paquette, Leo A.

  DOI：10.15227/orgsyn.069.0173

  日期：——
• Farmer; Ross, Journal of the Chemical Society, 1925, vol. 127, p. 2368
  作者：Farmer、Ross

  DOI：——

  日期：——
• POUPART, MARC-ANDRE;PAQUETTE, LEO A., TETRAHEDRON LETT., 29,(1988) N 3, 269-272
  作者：POUPART, MARC-ANDRE、PAQUETTE, LEO A.

  DOI：——

  日期：——
• Studies directed toward the total synthesis of cerorubenic acid-III. 1. Expedient construction of the tetracyclic core by oxyanionic sigmatropy
  作者：Leo A. Paquette、Marc Andre Poupart

  DOI：10.1021/jo00068a019

  日期：1993.7

  A synthesis of the ABCD ring framework of cerorubenic acid-III is described. Diketone 5 was first prepared by intramolecular oxidative coupling of the dienolate 10 and then suitably desymmetrized to deliver 15b. Anionic oxy-Cope rearrangement of this intermediate resulted in construction of 18, a ketone not only having all three contiguous stereogenic centers properly established but also equipped with adequate functionality for the further elaboration of ring D. In the present effort, this thrust took the form of homologation to 21, conversion to the activated diene 22, and Diels-Alder cycloaddition to methyl acrylate at high pressure. Once it became obvious that first-formed ketone 26 greatly preferred adoption of trans stereochemistry at the ring juncture, attempts to skirt this issue were made by preparing both 29 and 32. However, these advanced intermediates proved unresponsive to conjugate reduction, and attention was therefore redirected to alternative possible means for elaboration of the eastern sector.