(4R)-2,2-dimethyl-4-[(1R,2R)-2-methyl-1-prop-2-enoxybut-3-enyl]-1,3-dioxolane | 936016-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R)-2,2-dimethyl-4-[(1R,2R)-2-methyl-1-prop-2-enoxybut-3-enyl]-1,3-dioxolane
• CAS: 936016-77-2
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: DZNFDPBLSBFTSY-IJLUTSLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-2,2-dimethyl-4-[(1R,2R)-2-methyl-1-prop-2-enoxybut-3-enyl]-1,3-dioxolane 在 Wilkinson's catalyst 、 Grubbs catalyst first generation 2,6-二甲基吡啶 、 原乙酸三甲酯 、 正丁基锂 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 20.0h， 生成 [(Z,1R)-1-[(2R,3R)-6-(benzenesulfonyl)-3-methyloxan-2-yl]-6-tri(propan-2-yl)silyloxyhex-3-enoxy]-tri(propan-2-yl)silane
  参考文献：
  名称：

  A Reductive Cyclization Approach to Attenol A

  摘要：

  A reductive cyclization strategy was applied to the synthesis of attenol A. This nontraditional approach to the spiroacetal structure illustrated several advantages of the reductive cyclization methodology. The attenol A core was formed in a carbon-carbon bond coupling that gave rise to a previously inaccessible spiroacetal epimer, a new method to synthesize thioketene acetals from a phenyl sulfone was realized, and the configurational stability of a nonanomeric spiroacetal was evaluated. A minor byproduct in the reductive cyclization reaction was identified that for the first time allowed direct evaluation of the stereoselectivity in a reductive cyclization of a dialkyloxy alkyllithium reagent.

  DOI：

  10.1021/jo0626459
• 作为产物：
  描述：

  (1R,2R)-2-methyl-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 、 3-溴丙烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以95%的产率得到(4R)-2,2-dimethyl-4-[(1R,2R)-2-methyl-1-prop-2-enoxybut-3-enyl]-1,3-dioxolane
  参考文献：
  名称：

  A Reductive Cyclization Approach to Attenol A

  摘要：

  A reductive cyclization strategy was applied to the synthesis of attenol A. This nontraditional approach to the spiroacetal structure illustrated several advantages of the reductive cyclization methodology. The attenol A core was formed in a carbon-carbon bond coupling that gave rise to a previously inaccessible spiroacetal epimer, a new method to synthesize thioketene acetals from a phenyl sulfone was realized, and the configurational stability of a nonanomeric spiroacetal was evaluated. A minor byproduct in the reductive cyclization reaction was identified that for the first time allowed direct evaluation of the stereoselectivity in a reductive cyclization of a dialkyloxy alkyllithium reagent.

  DOI：

  10.1021/jo0626459

文献信息

• A Reductive Cyclization Approach to Attenol A
  作者：Thomas E. La Cruz、Scott D. Rychnovsky

  DOI：10.1021/jo0626459

  日期：2007.3.1

  A reductive cyclization strategy was applied to the synthesis of attenol A. This nontraditional approach to the spiroacetal structure illustrated several advantages of the reductive cyclization methodology. The attenol A core was formed in a carbon-carbon bond coupling that gave rise to a previously inaccessible spiroacetal epimer, a new method to synthesize thioketene acetals from a phenyl sulfone was realized, and the configurational stability of a nonanomeric spiroacetal was evaluated. A minor byproduct in the reductive cyclization reaction was identified that for the first time allowed direct evaluation of the stereoselectivity in a reductive cyclization of a dialkyloxy alkyllithium reagent.