3',3'-Dimethylspiro-4'-one | 82817-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 3',3'-Dimethylspiro-4'-one
• 英文别名: 3',3'-dimethylspiro[adamantane-2,4'-oxetane]-2'-one
• CAS: 82817-20-7
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: BRYWNFDWMINFMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3',3'-Dimethylspiro-4'-one 以95%的产率得到2-isopropylideneadamantane
  参考文献：
  名称：

  Adam, Waldemar; Encarnacion, Luis A. Arias, Chemische Berichte, 1982, vol. 115, # 7, p. 2592 - 2605

  摘要：

  DOI：
• 作为产物：
  描述：

  金刚烷酮 、 l'enolate lithie de l'isobutirate de methyle 以 四氢呋喃 为溶剂， 反应 4.0h， 以85%的产率得到3',3'-Dimethylspiro-4'-one
  参考文献：
  名称：

  Adam, Waldemar; Encarnacion, Luis A. Arias, Chemische Berichte, 1982, vol. 115, # 7, p. 2592 - 2605

  摘要：

  DOI：

文献信息

• Are β-Lactones Involved in Carbon-Based Olefination Reactions?
  作者：Michał Barbasiewicz、Jan Nowak、Michał Tryniszewski

  DOI：10.1055/a-2268-4386

  日期：2024.6

  methylmalonate, which converts electrophilic aryl aldehydes into α-methylcinnamates in up to 70% yield. The reaction plausibly proceeds through the formation of β-lactone that spontaneously decarboxylates under the reaction conditions. The results shed light on the Knoevenagel–Doebner olefination, for which decarboxylative anti-fragmentation of aldol-type adducts is usually considered.

  杂原子烯化试剂（如有机膦酸酯、磺酸酯等）用于将羰基化合物转化为烯烃，其作用机制涉及羟醛型加成、环化和四元环中间体的断裂。我们开发了一种使用 1,1,1,3,3,3-六氟异丙基甲基丙二酸乙酯的类似工艺，可将亲电芳基醛转化为 α-甲基肉桂酸酯，产率高达 70%。该反应似乎是通过形成β-内酯进行的，β-内酯在反应条件下自发脱羧。结果揭示了克诺文格尔-多布纳烯化反应，通常考虑羟醛型加合物的脱羧反断裂。
• Face selection in thermal cycloaddition and -reversion
  作者：Haifang Li、Jack E. Silver、William H. Watson、Ram P. Kashyap、William J. Le Noble

  DOI：10.1021/jo00020a041

  日期：1991.9

  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.
• ADAM, W.;ENCARNACION, L. A. A., CHEM. BER., 1982, 115, N 7, 2592-2605
  作者：ADAM, W.、ENCARNACION, L. A. A.

  DOI：——

  日期：——