(1S,4'R)-1-(2,2-dimethyl-1,3-dioxolane-4-yl)-3-methylbut-2-en-1-ol | 154842-34-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,4'R)-1-(2,2-dimethyl-1,3-dioxolane-4-yl)-3-methylbut-2-en-1-ol
• 英文别名: (1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-2-en-1-ol
• CAS: 154842-34-9
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: QYQQEVMHKGVKFQ-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,4'R)-1-(2,2-dimethyl-1,3-dioxolane-4-yl)-3-methylbut-2-en-1-ol 在 sodium tetrahydroborate 、 sodium hydride 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-O-benzyl-3,4-O-isopropylidene-D-erythritol (12) and 2-O-benzyl-3,4-O-isopropylidene-D-erythritol
  参考文献：
  名称：

  Diastereoselective addition of lower order vinylcuprates to (R)-2,3-O-Isopropylideneglyceraldehyde

  摘要：

  Highly syn or anti selective addition of lower order lithium vinylcuprates generated from alkenyl bromides 1 to (R)-2,3-O-isopropylideneglyceraldehyde (2) can be achieved, respectively, depending on the substitution pattern of the vinyl moiety and the solvent. Alpha-Trimethylsilyl substituted vinylcuprates possessing an alkyl substituent Z to copper react with excellent syn selectivity in ether whereas a highly anti selective addition is observed for cuprates bearing a hydrogen atom Z or alpha to the metal in THF. A model is proposed to rationalize these complementary selectivities.

  DOI：

  10.1016/s0040-4020(01)81551-9
• 作为产物：
  描述：

  1-溴-2-甲基-1-丙烯 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 copper(l) iodide 、 三丁基膦 、 叔丁基锂 作用下， 生成 (1R,4'R)-1-(2,2-dimethyl-1,3-dioxolane-4-yl)-3-methylbut-2-en-1-ol 、 (1S,4'R)-1-(2,2-dimethyl-1,3-dioxolane-4-yl)-3-methylbut-2-en-1-ol
  参考文献：
  名称：

  Diastereoselective addition of lower order vinylcuprates to (R)-2,3-O-Isopropylideneglyceraldehyde

  摘要：

  Highly syn or anti selective addition of lower order lithium vinylcuprates generated from alkenyl bromides 1 to (R)-2,3-O-isopropylideneglyceraldehyde (2) can be achieved, respectively, depending on the substitution pattern of the vinyl moiety and the solvent. Alpha-Trimethylsilyl substituted vinylcuprates possessing an alkyl substituent Z to copper react with excellent syn selectivity in ether whereas a highly anti selective addition is observed for cuprates bearing a hydrogen atom Z or alpha to the metal in THF. A model is proposed to rationalize these complementary selectivities.

  DOI：

  10.1016/s0040-4020(01)81551-9

文献信息

• Diastereoselective addition of lower order vinylcuprates to (R)-2,3-O-Isopropylideneglyceraldehyde
  作者：Peter Metz、Andreas Schoop

  DOI：10.1016/s0040-4020(01)81551-9

  日期：1993.1

  Highly syn or anti selective addition of lower order lithium vinylcuprates generated from alkenyl bromides 1 to (R)-2,3-O-isopropylideneglyceraldehyde (2) can be achieved, respectively, depending on the substitution pattern of the vinyl moiety and the solvent. Alpha-Trimethylsilyl substituted vinylcuprates possessing an alkyl substituent Z to copper react with excellent syn selectivity in ether whereas a highly anti selective addition is observed for cuprates bearing a hydrogen atom Z or alpha to the metal in THF. A model is proposed to rationalize these complementary selectivities.