methyl 2,2,4-trimethyl-1,3-dioxolane-4-carboxylate | 126971-16-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,2,4-trimethyl-1,3-dioxolane-4-carboxylate
• 英文别名: methyl (4S)-2,2,4-trimethyl-1,3-dioxolane-4-carboxylate
• CAS: 126971-16-2
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: OKSFTIJEDNYZJL-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,2,4-trimethyl-1,3-dioxolane-4-carboxylate 在 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (2,2,4-trimethyl-1,3-dioxolane-4-yl)methyl methanesulfonate
  参考文献：
  名称：

  An alternative approach to (S)- and (R)-2-methylglycidol O-benzyl ether derivatives

  摘要：

  This report describes the gram scale synthesis of (S)- and (R)-2,2,4-trimethyl-4-(hydroxymethyl)-1,3-dioxolanes using the Sharpless asymmetric dihydroxylation (AD) of the Weinreb amide of 2-methyl-2-propenoic acid. The 2-methylglycerol acetonides resultant from protection of the AD products were used as starting materials in the synthesis of O-benzyl ethers of the valuable C4-chiral building blocks (S)- and (X)-2-methylglycidol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00230-0
• 作为产物：
  描述：

  甲基2,3-二羟基-2-甲基丙酸酯 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以93%的产率得到methyl 2,2,4-trimethyl-1,3-dioxolane-4-carboxylate
  参考文献：
  名称：

  An alternative approach to (S)- and (R)-2-methylglycidol O-benzyl ether derivatives

  摘要：

  This report describes the gram scale synthesis of (S)- and (R)-2,2,4-trimethyl-4-(hydroxymethyl)-1,3-dioxolanes using the Sharpless asymmetric dihydroxylation (AD) of the Weinreb amide of 2-methyl-2-propenoic acid. The 2-methylglycerol acetonides resultant from protection of the AD products were used as starting materials in the synthesis of O-benzyl ethers of the valuable C4-chiral building blocks (S)- and (X)-2-methylglycidol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00230-0