(4R,5R)-5-iodo-4-methyl-hex-2(E)-enoic acid benzyl ester | 483968-52-1

• 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: (4R,5R)-5-iodo-4-methyl-hex-2(E)-enoic acid benzyl ester
• 英文别名: benzyl (E,4R,5S)-5-iodo-4-methylhex-2-enoate
• CAS: 483968-52-1
• 化学式: C₁₄H₁₇IO₂
• 分子量: 344.192
• InChiKey: LARWPANBQCXDJB-DGTDAXKGSA-N

物化性质

• 沸点：
  351.6±35.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,5R)-5-iodo-4-methyl-hex-2(E)-enoic acid benzyl ester 在 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (+/-)-dl-2-(cis-2-trans-3-dimethylcyclopropyl)acetic acid benzyl ester 、 meso-2-(trans-2-trans-3-dimethylcyclopropyl)acetic acid benzyl ester
  参考文献：
  名称：

  Investigation of SmI2-mediated cyclisation of δ-iodo-α,β-unsaturated esters by deuterium 2D NMR in oriented solvents

  摘要：

  We have investigated the mechanism of the SmI2-mediated cyclisation of delta-iodo-alpha,beta-unsaturated esters using proton-decoupled deuterium 1D and 2D NMR in weakly ordered polypeptide liquid crystal solvents. Analysis of the spectroscopic results demonstrates that the cyclisation reaction takes place with concomitant and extensive racemisation at the gamma-position and the reason for this racemisation is discussed. We also report an efficient 2D NMR strategy for distinguishing meso- from d- and l-diastereoisomers based on the introduction of a CD2 probe in the molecules to be studied. This approach allows determination of the diastereoisomeric and enantiomeric composition of a mixture. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00259-8
• 作为产物：
  描述：

  (苄氧羰基亚甲基)三苯基膦 在 四(三苯基膦)钯 咪唑 、 Oxone 、 二甲胺基甲硼烷 、 fructose-derived chiral ketone 、 Na₂B₂O₄*10H₂O 、 碘 、 溶剂黄146 、 三苯基膦 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.25h， 生成 (4R,5R)-5-iodo-4-methyl-hex-2(E)-enoic acid benzyl ester
  参考文献：
  名称：

  Investigation of SmI2-mediated cyclisation of δ-iodo-α,β-unsaturated esters by deuterium 2D NMR in oriented solvents

  摘要：

  We have investigated the mechanism of the SmI2-mediated cyclisation of delta-iodo-alpha,beta-unsaturated esters using proton-decoupled deuterium 1D and 2D NMR in weakly ordered polypeptide liquid crystal solvents. Analysis of the spectroscopic results demonstrates that the cyclisation reaction takes place with concomitant and extensive racemisation at the gamma-position and the reason for this racemisation is discussed. We also report an efficient 2D NMR strategy for distinguishing meso- from d- and l-diastereoisomers based on the introduction of a CD2 probe in the molecules to be studied. This approach allows determination of the diastereoisomeric and enantiomeric composition of a mixture. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00259-8