(1S)-3-chloro-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]but-3-en-1-ol | 1179318-36-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-3-chloro-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]but-3-en-1-ol
• CAS: 1179318-36-5
• 化学式: C₉H₁₅ClO₃
• 分子量: 206.669
• InChiKey: IRVRFWATVAFKAT-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二氯丙烯 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 indium 、 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 、 (1S)-3-chloro-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]but-3-en-1-ol
  参考文献：
  名称：

  A Sequential Indium-Mediated Aldehyde Allylation/Palladium-Catalyzed Cross-Coupling Reaction in the Synthesis of 2-Deoxy-β-C-Aryl Glycosides

  摘要：

  Indium-mediated allylation of aldehydes with 2-chloro-3-iodopropene, followed by a palladium-catalyzed cross-coupling reaction with triarylindium reagents or arylboronic acids, leads to aryl-substituted homoallylic alcohols in good to excellent yields and diastereoselectivities. The products obtained from reactions conducted with D-glyceraldehyde acetonide can be transformed into 2-deoxy-beta-C-aryl ribofuranosides in high overall yields. Similarly, 2-deoxy-beta-C-aryl allopyranosides may be prepared efficiently from 2,4-O-benzylidene erythrose.

  DOI：

  10.1021/ol901353f

文献信息

• A Sequential Indium-Mediated Aldehyde Allylation/Palladium-Catalyzed Cross-Coupling Reaction in the Synthesis of 2-Deoxy-β-<i>C</i>-Aryl Glycosides
  作者：John Alec Moral、Seong-Jin Moon、Samuel Rodriguez-Torres、Thomas G. Minehan

  DOI：10.1021/ol901353f

  日期：2009.8.20

  Indium-mediated allylation of aldehydes with 2-chloro-3-iodopropene, followed by a palladium-catalyzed cross-coupling reaction with triarylindium reagents or arylboronic acids, leads to aryl-substituted homoallylic alcohols in good to excellent yields and diastereoselectivities. The products obtained from reactions conducted with D-glyceraldehyde acetonide can be transformed into 2-deoxy-beta-C-aryl ribofuranosides in high overall yields. Similarly, 2-deoxy-beta-C-aryl allopyranosides may be prepared efficiently from 2,4-O-benzylidene erythrose.