meso-2,2,3,4,5,5-hexamethyl-hexane-3,4-diol | 118888-04-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: meso-2,2,3,4,5,5-hexamethyl-hexane-3,4-diol
• 英文别名: (3S,4R)-2,2,3,4,5,5-hexamethylhexane-3,4-diol
• CAS: 118888-04-3
• 化学式: C₁₂H₂₆O₂
• 分子量: 202.337
• InChiKey: QPOPZJSFBBPTOG-TXEJJXNPSA-N

物化性质

• 沸点：
  223.6±8.0 °C(Predicted)
• 密度：
  0.912±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,1'-thiobis(3,3-dimethylbutan-2-one) 在 四氯化钛 、 镍 、 锌 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 meso-2,2,3,4,5,5-hexamethyl-hexane-3,4-diol
  参考文献：
  名称：

  Synthesis and reactions of 3,4-di-t-butylthiophene

  摘要：

  DOI：

  10.1016/s0040-4039(00)86677-0

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.
• Lenoir,D., Chemische Berichte, 1978, vol. 111, p. 411 - 414
  作者：Lenoir,D.

  DOI：——

  日期：——
• LENOIR D., CHEM. BER., 1978, 111, NO 1, 411-414
  作者：LENOIR D.

  DOI：——

  日期：——