2-formyl-2-methylcycloheptanone | 130516-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-formyl-2-methylcycloheptanone
• 英文别名: 1-methyl-2-oxocycloheptane-1-carbaldehyde
• CAS: 130516-31-3
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: PYQOEZDXLDFWNN-UHFFFAOYSA-N

物化性质

• 沸点：
  69-72 °C(Press: 0.7 Torr)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-formyl-2-methylcycloheptanone 在 正丁基锂 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 23.0h， 生成 (2R,2aR,7aS,8R)-2-Benzyloxy-7a-hydroxy-2b-methyl-1-oxo-decahydro-8a-aza-cyclobuta[a]azulene-8-carboxylic acid methyl ester
  参考文献：
  名称：

  The Intramolecular Aldol Condensation Route to Fused Bi- and Tricyclic β-Lactams^1,2

  摘要：

  Staudinger cycloaddition of activated acid chlorides to 1,3-ketoaldimines, prepared in quantitative yields from 1,3-ketoaldehydes and amino esters, gave in excellent yields cis-a-azetidinones, 6-8, having the adequate functionality to obtain fused bi- and tricyclic beta-lactams. Reaction of compounds 6 with LHMDS at low temperature gave a single diastereomer of fused bicyclic compounds with a carbapenam or carbacefam skeleton. Treatment of diastereomeric cis-2-azetidinones, 7/8, in analogous conditions resulted either in the exclusive cyclization of one of the two diastereomers to form tricyclic [4.n.m] (n = 5, 6; m = 5, 6) compounds, or in the cyclization of both diastereomers to form tricyclic [4.n.7] (n = 5, 6) 2-azetidinones. In all cases the cyclization step was totally stereoselective. Alternatively, trans-carbapenams and one example of a tricyclic system having a trans-2-azetidinone ring have been obtained by using longer reaction times and higher temperatures. Epimerization at C3 of the 2-azetidinone nucleus occurs in these reaction conditions to obtain a single diastereomer of the final products. This approach to fused policyclic 2-azetidinones is one of the scarce syntheses of this kind of compound making use of the aldol condensation.

  DOI：

  10.1021/jo960904w
• 作为产物：
  描述：

  碘甲烷 、 2-(hydroxymethylene)cycloheptanone 在 potassium tert-butylate 作用下， 生成 2-formyl-2-methylcycloheptanone
  参考文献：
  名称：

  通过阴离子氧对位重排合成有角度取代的双环系统

  摘要：

  报道了使用阴离子氧基-Cope重排一般合成具有角甲基取代基的反式双环甲醇。的原醇，，，和提供双环原醇，，和当与氢化钾在1,2- dimethoxyeth ANE处理。

  DOI：

  10.1016/s0040-4020(01)81524-6

文献信息

• Studies in base-catalyzed allenic oxy-Cope rearrangement: an expedient synthesis of functionalized bicyclo[4.3.0] and -[4.4.0] systems and 3,5-cycloundecadien-1-one
  作者：Arumugham Balakumar、Selvasekaran Janardhanam、Krishnamoorthy Rajagopalan

  DOI：10.1021/jo00072a035

  日期：1993.9

  The base-catalyzed oxy-Cope rearrangement of systems incorporating an allenic pi system was studied. The rearrangement incidentally leads to functionalized bicyclo[4.3.0]nonane 15, bicyclo[4.4.0]decanes 6 and 10, and 3,5-cycloundecadien-1-one 20. The effect of ring size and nature of the base on the rearrangement was also studied.
• Janardhanam, Selvasekaran; Balakumar, Arumugham; Rajagopalan, Krishnamoorthy, Journal of the Chemical Society. Perkin transactions I, 1994, # 5, p. 551 - 556
  作者：Janardhanam, Selvasekaran、Balakumar, Arumugham、Rajagopalan, Krishnamoorthy

  DOI：——

  日期：——
• Armesto, Diego; Ramos, Ana; Ortiz, Maria J., Journal of the Chemical Society. Perkin transactions I, 1997, # 10, p. 1535 - 1541
  作者：Armesto, Diego、Ramos, Ana、Ortiz, Maria J.、Horspool, William M.、Mancheno, Maria J.、Caballero, Olga、Mayoral, Elena P.

  DOI：——

  日期：——
• SATHYAMOORTHI, G.;THANGARAJ, K.;SRINIVASAN, P. C.;SWAMINATHAN, S., TETRAHEDRON, 46,(1990) N0, C. 3559-3568
  作者：SATHYAMOORTHI, G.、THANGARAJ, K.、SRINIVASAN, P. C.、SWAMINATHAN, S.

  DOI：——

  日期：——