(1S,2S,4R)-1,4,5,6-Tetrabromo-7,7-dimethoxy-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid | 446300-57-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2S,4R)-1,4,5,6-Tetrabromo-7,7-dimethoxy-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• CAS: 446300-57-8
• 化学式: C₁₀H₁₀Br₄O₄
• 分子量: 513.803
• InChiKey: QZFKFXFZBKGTII-RMASGNQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R)-1,4,5,6-Tetrabromo-7,7-dimethoxy-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.5h， 生成 ((1S,2S,4R)-1,4,5,6-Tetrabromo-7,7-dimethoxy-bicyclo[2.2.1]hept-5-en-2-yl)-methanol
  参考文献：
  名称：

  摘要：

  Effect of the conditions on the enantiomeric purity, overall yield, and isomeric composition of chiral polybromonorbornene Diels-Alder adducts of polybromocyclopentadienes and (-)-menthyl acrylate was studied. Enantiomerically pure polybromonorbornenecarboxylic acids were obtained by resolution of the corresponding racemates through diastereoisomeric salts with l-ephedrine. The structure of the products was confirmed by the IR and H-1 NMR spectra.

  DOI：

  10.1023/a:1015386221273
• 作为产物：
  描述：

  (-)-menthyl 1,2,3,4-tetrabromo-7,7-dimethoxybicyclo[2.2.1]hept-2-ene-5-carboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (1S,2S,4R)-1,4,5,6-Tetrabromo-7,7-dimethoxy-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
  参考文献：
  名称：

  摘要：

  Effect of the conditions on the enantiomeric purity, overall yield, and isomeric composition of chiral polybromonorbornene Diels-Alder adducts of polybromocyclopentadienes and (-)-menthyl acrylate was studied. Enantiomerically pure polybromonorbornenecarboxylic acids were obtained by resolution of the corresponding racemates through diastereoisomeric salts with l-ephedrine. The structure of the products was confirmed by the IR and H-1 NMR spectra.

  DOI：

  10.1023/a:1015386221273

文献信息

• A stereoselective C7nC5x free-radical cascade route to optically pure and potentially useful tetracyclic amines
  作者：Faiz Ahmed Khan、Sarasij K. Upadhyay

  DOI：10.1016/j.tetlet.2008.08.013

  日期：2008.10

  Nucleophilic racemic amines have been synthesized utilizing a (CC5x)-C-7n free-radical cascade reaction from a bis-allyl amine starting material. Being potentially useful organocatalytic bases as is evident from their screening in the Baylis-Hillman reaction, optically pure amines were also synthesized from optically pure aldehydes (-) or (+)-4. Bis-allyl amides under similar radical reaction condition resulted in C-7n cyclized products. (C) 2008 Elsevier Ltd. All rights reserved.