4',5'-dimethylspiro | 99727-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫吡喃类
• 英文名称: 4',5'-dimethylspiro
• 英文别名: adamantane-2-spiro-(2'-4',5'-dimethylthiacyclohex-4'-ene)；4',5'-dimethylspiro(adamantane-2,2'-thiacyclohex-4'-ene)；3,4-Dimethylspiro[2,5-dihydrothiopyran-6,2'-adamantane]
• CAS: 99727-22-7
• 化学式: C₁₆H₂₄S
• 分子量: 248.433
• InChiKey: FJPKAQJJOFRUFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4',5'-dimethylspiro 在 Oxone 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 0.5h， 生成 3,4-dimethylspiro[2,5-dihydrothiopyran-6,2'-adamantane] 1-oxide
  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
• 作为产物：
  描述：

  金刚烷-2-硫酮 、 2,3-二甲基-1,3-丁二烯 以 甲苯 为溶剂， 以82%的产率得到4',5'-dimethylspiro
  参考文献：
  名称：

  Sasaki, Tadashi; Eguchi, Shoji; Katada, Tomonori, Heterocycles, 1984, vol. 21, # 2, p. 682

  摘要：

  DOI：

文献信息

• Synthesis of adamantane derivatives. 73. Thermal cycloaddition reactions of thiocarbonyl compounds. 4. Synthesis of novel adamantane-2-spirothiaheterocycles via [4 + 2] cycloaddition reactions of adamantanethione with conjugated dienes
  作者：Tomonori Katada、Shoji Eguchi、Tadashi Sasaki

  DOI：10.1021/jo00353a008

  日期：1986.2
• SASAKI, TADASHI;EGUCHI, SHOJI;KATADA, TOMONORI, HETEROCYCLES, 1984, 21, N 2, 682
  作者：SASAKI, TADASHI、EGUCHI, SHOJI、KATADA, TOMONORI

  DOI：——

  日期：——
• KATADA, TOMONORI;EGUCHI, SHOJI;SASAKI, TADASHI, J. ORG. CHEM., 1986, 51, N 3, 314-320
  作者：KATADA, TOMONORI、EGUCHI, SHOJI、SASAKI, TADASHI

  DOI：——

  日期：——
• 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.
• Sasaki, Tadashi; Eguchi, Shoji; Katada, Tomonori, Heterocycles, 1984, vol. 21, # 2, p. 682
  作者：Sasaki, Tadashi、Eguchi, Shoji、Katada, Tomonori

  DOI：——

  日期：——