(1R,5R)-1-(3,3-dibromo)allyl-3,3-dimethyl-2,4-dioxabicyclo[4.3.0]nonane | 210101-11-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,5R)-1-(3,3-dibromo)allyl-3,3-dimethyl-2,4-dioxabicyclo[4.3.0]nonane
• 英文别名: (3aR,7aR)-7a-(3,3-dibromoprop-2-enyl)-2,2-dimethyl-4,5,6,7-tetrahydro-3aH-1,3-benzodioxole
• CAS: 210101-11-4
• 化学式: C₁₂H₁₈Br₂O₂
• 分子量: 354.082
• InChiKey: PODGBLKBGFASOG-BXKDBHETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,5R)-1-(3,3-dibromo)allyl-3,3-dimethyl-2,4-dioxabicyclo[4.3.0]nonane 在 盐酸 、 正丁基锂 、 2-碘酰基苯甲酸 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 14.0h， 生成 (2R)-2-hydroxy-2-(3-trimethylsilylprop-2-ynyl)cyclohexan-1-one
  参考文献：
  名称：

  Enantioselective synthesis of 2-allyl and 2-(3-trimethylsilylpropargyl)-2-hydroxycyclohexanone using osmium-catalyzed asymmetric dihydroxylation

  摘要：

  The catalytic asymmetric dihydroxylation of (1-cyclohexenyl) or (1-cyclopentenyl) acetonitrile 5 and 15 with AD-mix-beta occurred with good enantiofacial selectivity (87 to 94.7% ee after recrystallization) giving (R,R)-diols in agreement with the mnemonic device. The 6-membered ring diol nitrile was easily transformed, via standard functional group manipulations, to 2-allyl and 2-(3-trimethylsilylprop-2-ynyl)-2-hydroxycyclohexanone in about 35% overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00144-x
• 作为产物：
  描述：

  1-环己烯乙腈 在 四氧化锇 、 甲基磺酰胺 、 AD-mix-β 、 camphor-10-sulfonic acid 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 24.5h， 生成 (1R,5R)-1-(3,3-dibromo)allyl-3,3-dimethyl-2,4-dioxabicyclo[4.3.0]nonane
  参考文献：
  名称：

  Enantioselective synthesis of 2-allyl and 2-(3-trimethylsilylpropargyl)-2-hydroxycyclohexanone using osmium-catalyzed asymmetric dihydroxylation

  摘要：

  The catalytic asymmetric dihydroxylation of (1-cyclohexenyl) or (1-cyclopentenyl) acetonitrile 5 and 15 with AD-mix-beta occurred with good enantiofacial selectivity (87 to 94.7% ee after recrystallization) giving (R,R)-diols in agreement with the mnemonic device. The 6-membered ring diol nitrile was easily transformed, via standard functional group manipulations, to 2-allyl and 2-(3-trimethylsilylprop-2-ynyl)-2-hydroxycyclohexanone in about 35% overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00144-x

文献信息

• Enantioselective synthesis of 2-allyl and 2-(3-trimethylsilylpropargyl)-2-hydroxycyclohexanone using osmium-catalyzed asymmetric dihydroxylation
  作者：Jean-Michel Devaux、Jacques Goré、Jean-Michel Vatèle

  DOI：10.1016/s0957-4166(98)00144-x

  日期：1998.5

  The catalytic asymmetric dihydroxylation of (1-cyclohexenyl) or (1-cyclopentenyl) acetonitrile 5 and 15 with AD-mix-beta occurred with good enantiofacial selectivity (87 to 94.7% ee after recrystallization) giving (R,R)-diols in agreement with the mnemonic device. The 6-membered ring diol nitrile was easily transformed, via standard functional group manipulations, to 2-allyl and 2-(3-trimethylsilylprop-2-ynyl)-2-hydroxycyclohexanone in about 35% overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.