3-(2-Adamantan-2-ylidene-propyl)-dihydro-furan-2,5-dione | 136175-84-3

• 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: 3-(2-Adamantan-2-ylidene-propyl)-dihydro-furan-2,5-dione
• CAS: 136175-84-3
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: JMAOLSGVXBVFGM-SXGWCWSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3',3'-Dimethylspiro-4'-one 以 氘代乙腈 为溶剂， 生成 3-(2-Adamantan-2-ylidene-propyl)-dihydro-furan-2,5-dione
  参考文献：
  名称：

  Face selection in thermal cycloaddition and -reversion

  摘要：

  The isomer distribution has been determined in several cycloaddition reactions involving 5-fluoro- and 5-phenyladamantane derivatives in which C2 serves as one of the trigonal termini. The reactions include a [2 + 2] cycloaddition with dichloroketene, a nucleophilic addition followed by cyclization, a [2 + 2] cycloreversion of a beta-lactone, and two Diels-Alder reactions; in the latter case, the adamantane moiety was incorporated in the diene in one instance and in the dienophile in the other. In all these reactions, the reagent attacking the adamantane substrate was found to do so preferentially at the zu face, by modest but clear margins. This observation is in accord with the concept of transition-state hyperconjugation. This explanation is extended to several literature examples involving substrates with faces that are not isosteric because the polarizing group is placed closer to the site of attack; the ratios are substantial and in favor of the more hindered product in many of these examples.

  DOI：

  10.1021/jo00020a041