1-(1-Adamantyl)-2-[2-(1-adamantyl)-2-oxoethyl]sulfanylethanone | 126226-69-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1-Adamantyl)-2-[2-(1-adamantyl)-2-oxoethyl]sulfanylethanone
• CAS: 126226-69-5
• 化学式: C₂₄H₃₄O₂S
• 分子量: 386.599
• InChiKey: NILVTKFMEIJQCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-Adamantyl)-2-[2-(1-adamantyl)-2-oxoethyl]sulfanylethanone 在 对甲苯磺酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以93%的产率得到3,6-di-1-adamantyl-2,7-dihydro-1,4,5-thiadiazepine
  参考文献：
  名称：

  通过 2,7-Dihydro-1,4,5-thiadiazepines 从 3-Thiapentane-1,5-dioones 制备 3,6-二取代哒嗪

  摘要：

  一系列 3-thiapentane-1,5-diones 与肼在催化量的对甲苯磺酸存在下在回流乙醇中缩合，以极好的收率得到 2,7-dihydro-1,4,5-thiadiazepines。后一种化合物在回流的二甘醇中热分解以高产率提供相应的哒嗪，并放出硫化氢。上述程序通常适用于制备各种具有结构意义且难以制备的 3,6-二取代哒嗪。

  DOI：

  10.1246/bcsj.62.2608
• 作为产物：
  描述：

  1-金刚烷基溴甲酮 在 sodium sulfide 作用下， 以 水 、 丙酮 为溶剂， 以100%的产率得到1-(1-Adamantyl)-2-[2-(1-adamantyl)-2-oxoethyl]sulfanylethanone
  参考文献：
  名称：

  通过 2,7-Dihydro-1,4,5-thiadiazepines 从 3-Thiapentane-1,5-dioones 制备 3,6-二取代哒嗪

  摘要：

  一系列 3-thiapentane-1,5-diones 与肼在催化量的对甲苯磺酸存在下在回流乙醇中缩合，以极好的收率得到 2,7-dihydro-1,4,5-thiadiazepines。后一种化合物在回流的二甘醇中热分解以高产率提供相应的哒嗪，并放出硫化氢。上述程序通常适用于制备各种具有结构意义且难以制备的 3,6-二取代哒嗪。

  DOI：

  10.1246/bcsj.62.2608

文献信息

• Preparation of Congested Thiophenes Carrying Bulky Substituents on the 3- and 4-Positions and Their Conversion to the Benzene Derivatives
  作者：Juzo Nakayama、Ryuji Hasemi、Koichi Yoshimura、Yoshiaki Sugihara、Shoji Yamaoka

  DOI：10.1021/jo971710z

  日期：1998.7.1

  Highly congested thiophenes, 3,4-di-tert-butyl-, 3,4-di(1-adamantyl)-, 3,4-dineopentyl-, and 3-(1-adamantyl)-4-tert-butylthiophenes (4a-d), were prepared in satisfactory overall yields by intramolecular reductive coupling of 3-thiapentane-1,5-diones (1a-d) followed by acid-catalyzed dehydration of the resulting thiolane-3,4-diols (2a-d). Experimental procedures of this; thiophene synthesis are fully described. Oxidation of the thiophenes 4a-d with m-CPBA gave the corresponding thiophene 1,1-dioxides 13a-d in good yields. The Diels-Alder reactions of 13a-d with phenyl vinyl sulfone gave o-di-tert-butyl-, o-di(1-adamantyl)-, o-dineopentyl-, and o-(1-adamantyl)-tert-butylbenzenes (17a-d) directly in high yields with loss of benzenesulfinic acid and sulfur dioxide. The dioxides 13a-d also underwent Diels-Alder reactions with alkynic dienophiles to give the corresponding benzene derivatives carrying two bulky substituents on adjacent positions. Pyridazines 25b,c, carrying bulky substituents on the 4- and 5-positions, were also synthesized through Diels-Alder reaction of 13b,c with PTAD. Dimethylation of the 2- and 5-positions of 13a-d was attained by treatment with strong bases followed by reactions with methyl iodide. The resulting tetrasubstituted thiophene 1,1-dioxides 14a-d reacted with DMAD to give highly congested hexasubstituted benzene derivatives 15a-d in good yields. Finally, structural features of the congested molecules are discussed on the basis of NMR analyses. Typically, the barriers to rotation (Delta H double dagger) about the benzene to the bulky substituents of 15a,c,d were determined to be 8.59, 15.3, and 7.40 kcal/mol, respectively, by NMR total line-shape analysis.
• The first synthesis of aromatic compounds carrying two 1-adamantyls on adjacent positions. 3,4-Di-1-adamantylthiophene, o-di-1-adamantylbenzene, and 4,5-di-1-adamantylpyridazine
  作者：Juzo Nakayama、Ryuji Hasemi

  DOI：10.1021/ja00170a048

  日期：1990.7
• NAKAYAMA, JUZO;KONISHI, TORU;ISHII, AKIHIKO;HOSHINO, MASAMATSU, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 2608-2612
  作者：NAKAYAMA, JUZO、KONISHI, TORU、ISHII, AKIHIKO、HOSHINO, MASAMATSU

  DOI：——

  日期：——
• NAKAYAMA, JUZO;HASEMI, RYUJI;IWASAKI, FUJIKO, PHOSPH., SULFUR AND SILICON AND RELAT. ELEM., 58-59,(1991) N-4, C. 243-24+
  作者：NAKAYAMA, JUZO、HASEMI, RYUJI、IWASAKI, FUJIKO

  DOI：——

  日期：——