3,3-dimethyl-4,5,6,7-tetrahydro-2H-indan-1-one | 30434-75-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-dimethyl-4,5,6,7-tetrahydro-2H-indan-1-one
• 英文别名: 4,5,6,7-tetrahydro-3,3-dimethyl-1-indanone；4,5,6,7-terahydro-3,3-dimethyl-1-indanone；3,3-Dimethyl-Δ^3a(7a)-tetrahydroindanon；3,3-Dimethyl-4,5,6,7-tetrahydroindan-1-on；3,3-Dimethyl-2,3,4,5,6,7-hexahydro-1H-inden-1-one；3,3-dimethyl-4,5,6,7-tetrahydro-2H-inden-1-one
• CAS: 30434-75-4
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: BDEIJJNYIYLEHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,3-dimethyl-4,5,6,7-tetrahydro-2H-indan-1-one 在 sodium tetrahydroborate 、 diisobutylaluminum hydride 、 盐酸羟胺 、 sodium 、 sodium hydride 、 三氯氧磷 作用下， 以 甲醇 、 乙醚 、 溶剂黄146 、 甲苯 为溶剂， 反应 35.5h， 生成 4,5,6,7-tetrahydro-1,1-dimethyl-2-formylindene
  参考文献：
  名称：

  Ito, Masayoshi; Kodama, Akiko; Tsukida, Kiyoshi, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 4, p. 1194 - 1197

  摘要：

  DOI：
• 作为产物：
  描述：

  1-环己烯-1-基(三甲基)硅烷 在 rhodium(III) chloride 、 三氯化铝 、 四氯化锡 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 37.25h， 生成 3,3-dimethyl-4,5,6,7-tetrahydro-2H-indan-1-one
  参考文献：
  名称：

  Silanes in organic synthesis. 8. Preparation of vinylsilanes from ketones and their regiospecific cyclopentenone annulation

  摘要：

  DOI：

  10.1021/jo01303a020

文献信息

• Vinylsilane mediated regiospecific cyclopentenone annulation of ketones
  作者：William E. Fristad、David S. Dime、Bailey Thomas R、Paquette Leo A

  DOI：10.1016/s0040-4039(01)86247-x

  日期：1979.1

  The development of a new cyclopentenone annulation sequence of general scope which involves Friedel-Crafts acylation of a vinylsilane with an α,β-unsaturated acid chloride followed by Nazarov cyclization is reported.

  据报道，开发了一种新的通用范围的环戊烯酮环化顺序，该顺序涉及乙烯基硅烷与α，β-不饱和酰氯的弗瑞德-克来福特（Friedel-Crafts）酰化，然后进行纳扎罗夫环化。
• Acylation of alkenes generated in situ by hydride transfer from isoalkanes. Synthesis of pentalenones, hydrindenones, and cyclopentenones
  作者：Christophe Morel-Fourrier、Jean Pierre Dulcere、Maurice Santelli

  DOI：10.1021/ja00021a036

  日期：1991.10

  Acylation, in the presence of AlCl3 and hydride acceptor, of methylcyclopentane, methylcyclohexane, and 2-methylbutane by ethylenic acyl chlorides, in CH2Cl2 solution, respectively, leads to tetrahydropentalenones, tetrahydroindenones, and cyclopentenones in good yields. Hydride acceptor may be either acetyl chloride or the alkenoyl chloride itself. Better results are performed in the presence of nitromethane and CuSO4. Overall yields are better than those obtained by the two-step process involving acylation of alkenes by alkenoyl chlorides and subsequent Nazarov cyclization of the resulting divinylketones. Methyl 1,4-migration is observed during the acylation of 2-methylbutane by sorboyl chloride. The mechanism of these conversions is discussed on the basis of results observed with cyclohexane-d12 and methylbutane-d6 as well as stereochemical studies of the cyclization process.
• Conia,J.-M.; Leriverend,M.-L., Bulletin de la Societe Chimique de France, 1970, p. 2981 - 2991
  作者：Conia,J.-M.、Leriverend,M.-L.

  DOI：——

  日期：——
• Ito, Masayoshi; Komada, Akiko; Tsukida, Kiyoshi, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 2, p. 679 - 681
  作者：Ito, Masayoshi、Komada, Akiko、Tsukida, Kiyoshi

  DOI：——

  日期：——
• FRAGMENTATION-RECOMBINATION NAZAROV CYCLIZATION: 3,4-DIMETHYLCYCLOPENT-2-EN-1-ONE
  作者：Schwartz, Keith D.、White, James D.、Tosaki, Shin-ya、Shibasaki, Masakatsu

  DOI：10.15227/orgsyn.083.0049

  日期：——