diethyl (4R,5R)-2-tert-butyl-2-methyl-1,3-dioxolane-4,5-dicarboxylate | 491863-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl (4R,5R)-2-tert-butyl-2-methyl-1,3-dioxolane-4,5-dicarboxylate
• 英文别名: (4R,5R)-2-tert-butyl-4,5-diethoxycarbonyl-2-methyldioxolane；Diethyl (4r,5r)-2-t-butyl-2-methyl-1,3-dioxolane-4,5-dicarboxylate
• CAS: 491863-34-4
• 化学式: C₁₄H₂₄O₆
• 分子量: 288.341
• InChiKey: FFCXWYWXJKDJDK-NXEZZACHSA-N

物化性质

• 沸点：
  325.6±37.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl (4R,5R)-2-tert-butyl-2-methyl-1,3-dioxolane-4,5-dicarboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以79%的产率得到(4S,5S)-2-tert-butyl-4,5-dihydroxymethyl-2-methyldioxolane
  参考文献：
  名称：

  摘要：

  Condensation of (4S,5S)-4,5-dihydroxymethyl-2-substituted dioxolanes with polyethylene glycols ditosylates yielded new chiral crown ethers. By potentiometry the enantioselectivity of complexing between the compounds obtained and L- and D-valine methyl ester hydrochlorides was evaluated.

  DOI：

  10.1023/a:1020315910332
• 作为产物：
  描述：

  频哪酮 、 L-(+)-酒石酸二乙酯 在 对甲苯磺酸 原甲酸三甲酯 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 diethyl (4R,5R)-2-tert-butyl-2-methyl-1,3-dioxolane-4,5-dicarboxylate
  参考文献：
  名称：

  在相转移反应中开发新型不对称两中心催化剂

  摘要：

  设计了一种新的不对称两中心相转移催化剂，并建立了包含40多种新的两中心催化剂的催化剂库。将催化剂用于相转移烷基化和迈克尔加成中，以分别提供至多93％ee和82％ee的相应产物。

  DOI：

  10.1016/s0040-4039(02)02416-4

文献信息

• Synthesis and Enantiodifferentiating Properties of Chiral Aza Crown Ethers
  作者：A. V. Lobach、O. N. Leus、N. Yu. Titova、N. G. Luk'yanenko

  DOI：10.1023/b:rujo.0000003200.41968.46

  日期：2003.7

  Alkylation of 2-substituted (4S,5S)-4,5-bis(hydroxymethyl)-1,3-dioxolanes with 9-benzyl-1,17-di-iodo-3,6,12,15-tetraoxa-9-azaheptadecane afforded new chiral aza and diaza crown ethers as a result of [1+1] and [2+2] additions. Their catalytic debenzylation gave the corresponding derivatives with a secondary amino group. The reaction of diethyl (+)-tartrate and diethyl (4S,5S)-1,3-dioxolane-4,5-diacetates with 1,8-diamino-3,6-dioxaoctane led to formation of chiral macrocyclic lactams which were reduced with lithium aluminum hydride. The resulting diaza crown ethers were tested for enantioselectivity in complex formation with L- and D-valine methyl ester by the potentiometric method. In most cases, the aza crown ethers showed better enantioselectivity than their oxygen analogs.
• Stereoselectivity of Grignard Reaction in the Presence of Chiral Podands and Crown Ethers
  作者：N. G. Luk'yanenko、A. V. Lobach、O. N. Leus

  DOI：10.1023/b:rujo.0000034953.76058.e4

  日期：2004.2

  Reactions of ethylmagnesium bromide with benzaldehyde and acetophenone in toluene proceed stereoselectively in the presence of catalytic amounts of chiral podands and crown ethers. Under catalytic conditions theyield of the corresponding alcohols is nearly quantitative. The optical yield varies in the range 9-86% depending on the catalyst structure.