(S,S)-2-bromo-4,4-bis(ethoxycarbonyl)-5-[4,5-bis[(benzyloxy)methyl]-1,3-dioxolan-2-yl]-1-pentene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S,S)-2-bromo-4,4-bis(ethoxycarbonyl)-5-[4,5-bis[(benzyloxy)methyl]-1,3-dioxolan-2-yl]-1-pentene
• 英文别名: diethyl 2-[[(4S,5S)-4,5-bis(phenylmethoxymethyl)-1,3-dioxolan-2-yl]methyl]-2-(2-bromoprop-2-enyl)propanedioate
• 化学式: C₃₀H₃₇BrO₈
• 分子量: 605.523
• InChiKey: BFFRYUNDQLBBQY-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S,S)-2-bromo-4,4-bis(ethoxycarbonyl)-5-[4,5-bis[(benzyloxy)methyl]-1,3-dioxolan-2-yl]-1-pentene 在 偶氮二异丁腈 、 三丁基氯化锡 、 sodium cyanoborohydride 作用下， 以 叔丁醇 为溶剂， 反应 5.0h， 以45%的产率得到diethyl (2S,3S,9S^*)-2,3-bis[(benzyloxy)methyl]-6-methyl-1,4-dioxaspiro[4,4]nonane-8,8-dicarboxylate
  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
• 作为产物：
  描述：

  (-)-1,4-O-二苯基-L-苏醇 、 Diethyl 2-(2-bromoprop-2-enyl)-2-(2,2-diethoxyethyl)propanedioate 在 camphor-10-sulfonic acid 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以78%的产率得到(S,S)-2-bromo-4,4-bis(ethoxycarbonyl)-5-[4,5-bis[(benzyloxy)methyl]-1,3-dioxolan-2-yl]-1-pentene
  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.