2-(2-ethynyl-cyclohex-1-enylmethyl)-2-(2-methyl-allyl)-malonic acid dimethyl ester | 1187458-50-9

• 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: 2-(2-ethynyl-cyclohex-1-enylmethyl)-2-(2-methyl-allyl)-malonic acid dimethyl ester
• CAS: 1187458-50-9
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: NSJVHNKFGXHRJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(2-ethynyl-cyclohex-1-enylmethyl)-2-(2-methyl-allyl)-malonic acid dimethyl ester 在 2-二环己基膦-2′,4′,6′-三异丙基联苯金(I) 双(三氟甲烷磺酰)亚胺 作用下， 以 二氯甲烷-D2 为溶剂， 反应 0.08h， 以85%的产率得到2a-methyl-2a,3,6,7,8,9-hexahydro-2H,5H-benzo[a]cyclobuta[c]cycloheptene-4,4-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Cyclobutenes作为金（I）催化的1,8-烯炔的环异构化中的可分离中间体

  摘要：

  Abstractmagnified imageThe gold(I)‐catalysed isomerisation of 1,8‐enynes allows the efficient synthesis of functionalised bicyclo[5.2.0]nonenes. Notably, these cyclobutenes derivatives can be isolated as reactive intermediates that could undergo subsequent gold(I)‐catalysed transformations such as isomerisation, fragmentation or ene reaction to furnish more structurally complex products. This study also provides useful information related to the mechanism leading to metathesis‐type derivatives, examples of which were shown to be produced, in the present case, by a gold(I)‐catalysed ring fragmentation of the cyclobutene moiety.

  DOI：

  10.1002/adsc.200900056
• 作为产物：
  描述：

  1-(bromomethyl)-2-ethynylcyclohexene 、 dimethyl (2-methyl-2-propenyl)-propanedioate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到2-(2-ethynyl-cyclohex-1-enylmethyl)-2-(2-methyl-allyl)-malonic acid dimethyl ester
  参考文献：
  名称：

  Cyclobutenes作为金（I）催化的1,8-烯炔的环异构化中的可分离中间体

  摘要：

  Abstractmagnified imageThe gold(I)‐catalysed isomerisation of 1,8‐enynes allows the efficient synthesis of functionalised bicyclo[5.2.0]nonenes. Notably, these cyclobutenes derivatives can be isolated as reactive intermediates that could undergo subsequent gold(I)‐catalysed transformations such as isomerisation, fragmentation or ene reaction to furnish more structurally complex products. This study also provides useful information related to the mechanism leading to metathesis‐type derivatives, examples of which were shown to be produced, in the present case, by a gold(I)‐catalysed ring fragmentation of the cyclobutene moiety.

  DOI：

  10.1002/adsc.200900056