(7aS)-5,6-dihydroxy-7a-methyl-3,5,6,7-tetrahydro-2H-inden-1-one | 959470-25-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (7aS)-5,6-dihydroxy-7a-methyl-3,5,6,7-tetrahydro-2H-inden-1-one
• CAS: 959470-25-8
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: PWAMDVIPYYUQGE-KTOWXAHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (7aS)-5,6-dihydroxy-7a-methyl-3,5,6,7-tetrahydro-2H-inden-1-one 、 lead(IV) tetraacetate 以 甲苯 为溶剂， 反应 0.08h， 以42 mg的产率得到acetic acid (1R,3R,7S,8R,9S)-9-acetoxy-7-methyl-6-oxo-2,10-dioxatricyclo[5.3.1.0^3,8]undec-3-yl ester
  参考文献：
  名称：

  Microwave-assisted domino reactions: function-compatibility, modulation, and greening efforts

  摘要：

  Herein we report a microwave-assisted version of a domino protocol, providing ready access to a wide variety of complex oxygen heterocycles. The latter can be converted to stereochemically, well-defined, variously substituted carbocycles, since reaction conditions and the substitution pattern can be tailored to fit a particular type of transformation. Microwave assistance, the influence of solvent, temperature, the function compatibility, and the use of PhI(OAc)(2) as a domino promoter are investigated. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.026
• 作为产物：
  描述：

  C₁₂H₁₈O₄ 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到(7aS)-5,6-dihydroxy-7a-methyl-3,5,6,7-tetrahydro-2H-inden-1-one
  参考文献：
  名称：

  A Domino-Based Approach toward Stereodefined Heavily Functionalized Cyclohexanes:  Synthesis of Iridal's Core Structure

  摘要：

  A stereoselective synthesis of heavily functionalized six-membered ring subunits, which possess functionality at sites appropriate for further elaboration, is described. The cyclopentanone moiety of hydrindenediol is required to achieve total facial selectivity during the pre-domino installation of the second quaternary center, while oxidative cleavage is responsible for the ring-expanding rearrangement. A microwave-assisted version of the key domino transformation and a test of concept approach toward the iridal core structure are also presented.

  DOI：

  10.1021/ol702056s