diethyl 2-(2-bromoprop-2-enyl)-2-[[(1R,4S,6S,8S)-2,2,11,11-tetramethyl-3,5-dioxatricyclo[6.2.1.01,6]undecan-4-yl]methyl]propanedioate | 186038-33-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diethyl 2-(2-bromoprop-2-enyl)-2-[[(1R,4S,6S,8S)-2,2,11,11-tetramethyl-3,5-dioxatricyclo[6.2.1.01,6]undecan-4-yl]methyl]propanedioate
• CAS: 186038-33-5
• 化学式: C₂₄H₃₇BrO₆
• 分子量: 501.458
• InChiKey: NPDJUDSWDXHLKQ-KOAQGZTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 2-(2-bromoprop-2-enyl)-2-[[(1R,4S,6S,8S)-2,2,11,11-tetramethyl-3,5-dioxatricyclo[6.2.1.01,6]undecan-4-yl]methyl]propanedioate 在 双(乙腈)氯化钯(II) 、 三正丁基氢锡 作用下， 生成 (S)-3-Methyl-4-oxo-cyclopentane-1,1-dicarboxylic acid diethyl ester 、 (R)-3-Methyl-4-oxo-cyclopentane-1,1-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Diastereoselective Cyclizations of 1,3-Dioxan-2-yl Radicals:  Chiral Acyl Radical Equivalents

  摘要：

  DOI：

  10.1021/jo960705c
• 作为产物：
  描述：

  (1R,4S)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid methyl ester 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 lutidine 、 四丁基氟化铵 、 L-Selectride 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 diethyl 2-(2-bromoprop-2-enyl)-2-[[(1R,4S,6S,8S)-2,2,11,11-tetramethyl-3,5-dioxatricyclo[6.2.1.01,6]undecan-4-yl]methyl]propanedioate
  参考文献：
  名称：

  Designed Chiral Acyl Radical Equivalents. Preparation and Cyclizations of Disymmetrically Substituted 1,3-Dioxabicyclo[4.4.0]decan-2-yl Radicals

  摘要：

  The diastereoselectivity of 5-exo-trigonal cyclizations of 2-(4 2-(4penten-1-yl)-1,3-dioxolan-2-yl and 2-(4penten-1-yl)-1,3-dioxan-2-yl radicals is investigated. When dioxolanes or dioxanes derived from C-2 symmetrically substituted diols are employed the diastereoselectivity is poor. In the dioxanyl series this is a consequence of the cyclization occurring through a twist-boat conformer. Disymmetrically substituted dioxanyl radicals, derived from the alcohols 21 and 41, are, however, constrained to chairlike conformations and accordingly give rise to highly diastereoselective cyclizations. Conditions are described for the hydrolysis of the resulting spiroacetals and for determination of the ee of the resulting 2-methylcyclopentanones.

  DOI：

  10.1021/jo961750n

文献信息

• Designed Chiral Acyl Radical Equivalents. Preparation and Cyclizations of Disymmetrically Substituted 1,3-Dioxabicyclo[4.4.0]decan-2-yl Radicals
  作者：D. Stien、R. Samy、R. Nouguier、D. Crich、M. P. Bertrand

  DOI：10.1021/jo961750n

  日期：1997.1.1

  The diastereoselectivity of 5-exo-trigonal cyclizations of 2-(4 2-(4penten-1-yl)-1,3-dioxolan-2-yl and 2-(4penten-1-yl)-1,3-dioxan-2-yl radicals is investigated. When dioxolanes or dioxanes derived from C-2 symmetrically substituted diols are employed the diastereoselectivity is poor. In the dioxanyl series this is a consequence of the cyclization occurring through a twist-boat conformer. Disymmetrically substituted dioxanyl radicals, derived from the alcohols 21 and 41, are, however, constrained to chairlike conformations and accordingly give rise to highly diastereoselective cyclizations. Conditions are described for the hydrolysis of the resulting spiroacetals and for determination of the ee of the resulting 2-methylcyclopentanones.
• Diastereoselective Cyclizations of 1,3-Dioxan-2-yl Radicals:  Chiral Acyl Radical Equivalents
  作者：Michèle P. Bertrand、David Crich、Robert Nouguier、Raghu Samy、Didier Stien

  DOI：10.1021/jo960705c

  日期：1996.1.1