3-(2'-Naphthylthio)-5,7-dimethyl-6-hydroxycyclooct-1-ene | 140657-22-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(2'-Naphthylthio)-5,7-dimethyl-6-hydroxycyclooct-1-ene
• 英文别名: (1S,2S,4Z,6S,8R)-2,8-dimethyl-6-naphthalen-2-ylsulfanylcyclooct-4-en-1-ol
• CAS: 140657-22-3
• 化学式: C₂₀H₂₄OS
• 分子量: 312.476
• InChiKey: IOGPWBMKFZYJSN-DVCVGLBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Lithium;naphthalene-2-thiolate 、 alkaline earth salt of/the/ methylsulfuric acid 在 溴 、 氧气 作用下， 生成 3-(2'-Naphthylthio)-5,7-dimethyl-6-hydroxycyclooct-1-ene
  参考文献：
  名称：

  Stereocontrolled functionalization of 1,5-cyclooctadiene using organomolybdenum chemistry

  摘要：

  The preparation and reactions of several new functionalized eta-3-cyclooctenyl-Mo(CO)2CP complexes are described. Dicarbonyl(eta-5-cyclopentadienyl)(1-3-eta-cycloocta-1,5-dienyl)molybdenum (6a) undergoes regio- and stereoselective hydroboration to give dicarbonyl(eta-5-cyclopentadienyl)(1-3-eta-6-endo-hydroxycyclooctenyl)molybdenum (7) as the major product. Swern oxidation of 7 proceeds cleanly to give dicarbonyl(eta-5-Cyclopentadienyl) (1-3-eta-6-oxo-cylooctenyl) molybdenum (9). Reactions of 9 with nucleophiles proceed with excellent stereoselectivity (anti to the Mo(CO)2Cp moiety). Conversion of 9 to enol silanes and thence to enolates is readily accomplished, and reaction of the enol silanes and enolates with electrophiles proceeds with complete stereoselectivity to give substituted ketones. Further regio- and stereoselective conversion of these substituted ketones to enolates and thence to disubstituted ketones is described. The stereochemical outcome of these reactions is discussed in terms of the preferred conformations for the enolates. Demetalation of dicarbonyl(eta-5-cyclopentadienyl)(1-3-eta-6-endo-hydroxy-5,7-endo-dimethylcyclooctenyl)molybdenum (23) to give a stereodefined tetrasubstituted cyclooctene 27 is described.

  DOI：

  10.1021/jo00036a028