methyl trans-5-methoxy-2,3-dimethyl-2-cyclohexene-1-carboxylate | 111026-08-5

• 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
• 英文名称: methyl trans-5-methoxy-2,3-dimethyl-2-cyclohexene-1-carboxylate
• 英文别名: trans-methyl 2,3-dimethyl-5-methoxy-2-cyclohexene-1-carboxylate；methyl (1R,5R)-5-methoxy-2,3-dimethylcyclohex-2-ene-1-carboxylate
• CAS: 111026-08-5
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: DSLQXKXCZHGZJU-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl trans-5-methoxy-2,3-dimethyl-2-cyclohexene-1-carboxylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 cis-methyl 2,3-dimethyl-5-methoxy-2-cyclohexene-1-carboxylate
  参考文献：
  名称：

  Calculation of NMR observables from computed conformers as a tool of structure verification. Confirmation of the stereochemistry of trans-methyl 2,3-dimethyl-5-methoxy-2-cyclohexene-1-carboxylate

  摘要：

  Four different methods (MM2, Chem3D, AM1, and MNDO) have been employed to calculate all the low-energy conformers of trans- and cis-methyl 2,3-dimethyl-5-methoxy-2-cyclohexene-1-carboxylate (1 and 2). For all of these conformers, NOE effects and vicinal coupling constants have been calculated, the latter using two different Karplus-type equations. From these calculations, 12 different sets of NMR observables were computed by taking a population weighted average over all conformations. These results were then used to verify the originally assigned trans configuration of compound 1. The diastereoisomer 2 was also prepared and shown to have the cis configuration. The different methods and the main sources of error are discussed. We found the best method for our purposes to be calculation of NOE from molecular mechanics structures.

  DOI：

  10.1021/jo00058a020
• 作为产物：
  描述：

  重氮甲烷 、 methyl trans-5-hydroxy-2,3-dimethyl-2-cyclohexene-1-carboxylate 在 四氟硼酸-二乙醚络合物 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 以63%的产率得到methyl trans-5-methoxy-2,3-dimethyl-2-cyclohexene-1-carboxylate
  参考文献：
  名称：

  1,4-Diene-derived (.eta.3-allyl)palladium complexes. 4. trans-Bis(5-alkoxy- and 5-hydroxy-1-3-.eta.3-cyclohexenyl)palladium complexes by palladium(II)-promoted addition of alcohols and water to 1,2-dialkyl-1,4-cyclohexadienes

  摘要：

  DOI：

  10.1021/jo00266a022

文献信息

• 1,4-Diene-derived (.eta.3-allyl)palladium complexes. Part 3. Trans-Bis(5-methoxy-1,3-3-cyclohexenyl)palladium complexes by palladium(II)-promoted addition of methanol to 1,4-cyclohexadienes. Synthesis of methyl trans-5-methoxy-2-cyclohexene-1-carboxylates by subsequent methoxycarbonylation
  作者：Bjoern C. Soederberg、Bjoern Aakermark、Stan S. Hall

  DOI：10.1021/jo00248a007

  日期：1988.6
• AKERMARK, BJORN;SODERBERG, BJORN C.;HALL, STAN S., J. ORG. CHEM., 54,(1989) N, C. 1110-1116
  作者：AKERMARK, BJORN、SODERBERG, BJORN C.、HALL, STAN S.

  DOI：——

  日期：——
• SODERBERG, BJORN C.;AKERMARK, BJORN;HALL, STAN S., J. ORG. CHEM., 53,(1988) N 13, 2925-2937
  作者：SODERBERG, BJORN C.、AKERMARK, BJORN、HALL, STAN S.

  DOI：——

  日期：——
• 1,4-Diene-derived (.eta.3-allyl)palladium complexes. 4. trans-Bis(5-alkoxy- and 5-hydroxy-1-3-.eta.3-cyclohexenyl)palladium complexes by palladium(II)-promoted addition of alcohols and water to 1,2-dialkyl-1,4-cyclohexadienes
  作者：Bjoern Aakermark、Bjoern C. Soederberg、Stan S. Hall

  DOI：10.1021/jo00266a022

  日期：1989.3
• Calculation of NMR observables from computed conformers as a tool of structure verification. Confirmation of the stereochemistry of trans-methyl 2,3-dimethyl-5-methoxy-2-cyclohexene-1-carboxylate
  作者：Jeffrey T. Martin、Per Ola Norrby、Bjoern Aakermark

  DOI：10.1021/jo00058a020

  日期：1993.3

  Four different methods (MM2, Chem3D, AM1, and MNDO) have been employed to calculate all the low-energy conformers of trans- and cis-methyl 2,3-dimethyl-5-methoxy-2-cyclohexene-1-carboxylate (1 and 2). For all of these conformers, NOE effects and vicinal coupling constants have been calculated, the latter using two different Karplus-type equations. From these calculations, 12 different sets of NMR observables were computed by taking a population weighted average over all conformations. These results were then used to verify the originally assigned trans configuration of compound 1. The diastereoisomer 2 was also prepared and shown to have the cis configuration. The different methods and the main sources of error are discussed. We found the best method for our purposes to be calculation of NOE from molecular mechanics structures.