1-(t-butyldimethylsiloxy)-1-(1,2-dioxopentyl)cyclohexane | 1215003-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(t-butyldimethylsiloxy)-1-(1,2-dioxopentyl)cyclohexane
• 英文别名: 1-[1-[Tert-butyl(dimethyl)silyl]oxycyclohexyl]pentane-1,2-dione
• CAS: 1215003-32-9
• 化学式: C₁₇H₃₂O₃Si
• 分子量: 312.525
• InChiKey: VCRIGLDZWWDIPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(t-butyldimethylsiloxy)-1-(1,2-dioxopentyl)cyclohexane 在 二苯甲酮 作用下， 以 氘代苯 为溶剂， 反应 0.67h， 以59%的产率得到c-7-hydroxy-r-1-(t-butyldimethylsiloxy)-7-propylbicyclo[4.2.0]octan-8-one
  参考文献：
  名称：

  Regio- and stereoselective acylation of saturated carbocycles via Norrish–Yang photocyclization

  摘要：

  A regio- and stereoselective acylation of saturated carbocycles has been achieved through two-step reactions involving the Norrish-Yang photocyclization of 1,2-diketones and subsequent ring opening of the alpha-hydroxy-cyclobutanones. The C-H activation of the carbocycle proceeds regioselectively at vicinal to the diketone moiety resulting in stereoselective formation of cis-fused bicycles. The following C-C cleavage affords vicinally cis-acylated carbocycles. Predictability, generality, and practicality of the present strategy have been demonstrated using variously modified saturated carbocycles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.027
• 作为产物：
  描述：

  1-(t-butyldimethylsiloxy)-1-(1-pentynyl)cyclohexane 在 sodium periodate 、 ruthenium(IV) oxide hydrate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 以76%的产率得到1-(t-butyldimethylsiloxy)-1-(1,2-dioxopentyl)cyclohexane
  参考文献：
  名称：

  Regio- and stereoselective acylation of saturated carbocycles via Norrish–Yang photocyclization

  摘要：

  A regio- and stereoselective acylation of saturated carbocycles has been achieved through two-step reactions involving the Norrish-Yang photocyclization of 1,2-diketones and subsequent ring opening of the alpha-hydroxy-cyclobutanones. The C-H activation of the carbocycle proceeds regioselectively at vicinal to the diketone moiety resulting in stereoselective formation of cis-fused bicycles. The following C-C cleavage affords vicinally cis-acylated carbocycles. Predictability, generality, and practicality of the present strategy have been demonstrated using variously modified saturated carbocycles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.027

文献信息

• Regio- and stereoselective acylation of saturated carbocycles via Norrish–Yang photocyclization
  作者：Shin Kamijo、Tamaki Hoshikawa、Masayuki Inoue

  DOI：10.1016/j.tetlet.2009.12.027

  日期：2010.2

  A regio- and stereoselective acylation of saturated carbocycles has been achieved through two-step reactions involving the Norrish-Yang photocyclization of 1,2-diketones and subsequent ring opening of the alpha-hydroxy-cyclobutanones. The C-H activation of the carbocycle proceeds regioselectively at vicinal to the diketone moiety resulting in stereoselective formation of cis-fused bicycles. The following C-C cleavage affords vicinally cis-acylated carbocycles. Predictability, generality, and practicality of the present strategy have been demonstrated using variously modified saturated carbocycles. (C) 2009 Elsevier Ltd. All rights reserved.