(2,2-dimethyl-1,3-dioxolane-4-yl)methyl p-nitrobenzoate | 61656-62-0

• 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: (2,2-dimethyl-1,3-dioxolane-4-yl)methyl p-nitrobenzoate
• 英文别名: (RS)-1,2-O-isopropylidene glycerol 4-nitrobenzoate；1,2-O-isopropylidenegycerol p-nitrobenzoate；(RS)-1,2-O-isopropylidene glycerol p-nitrobenzoate；2,2-dimethyl-4-(4-nitro-benzoyloxymethyl)-[1,3]dioxolane；2,2-Dimethyl-4-(4-nitro-benzoyloxymethyl)-[1,3]dioxolan；Benzoic acid, 4-nitro-, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl ester；(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-nitrobenzoate
• CAS: 61656-62-0
• 化学式: C₁₃H₁₅NO₆
• 分子量: 281.265
• InChiKey: NKDPWBPFSRNLRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2,2-dimethyl-1,3-dioxolane-4-yl)methyl p-nitrobenzoate 在 溶剂黄146 作用下， 生成 (R)-glycerol mono-p-nitrobenzoate 、 (S)-1-(4-Nitrobenzoyloxy)-2,3-propanediol
  参考文献：
  名称：

  p-Nitrobenzoate esters of epoxy alcohols: convenient synthons for water-soluble epoxy alcohols

  摘要：

  DOI：

  10.1021/jo00380a032
• 作为产物：
  描述：

  丙酮缩甘油 、 对硝基苯甲酸 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到(2,2-dimethyl-1,3-dioxolane-4-yl)methyl p-nitrobenzoate
  参考文献：
  名称：

  使用树脂结合的三苯基膦对对称二元醇进行选择性单酯化

  摘要：

  制备酯和酰胺的偶联反应是应用最广泛的有机转化方法之一。我们报道了高效的酰胺键形成步骤和对称二醇的单酯化，收率很高，而无需使用树脂结合的三芳基碘化high进行高稀释或缓慢添加。该方案的主要优点是易于纯化，对水分的敏感性低，并且产品的收率好至极佳。

  DOI：

  10.1021/acscombsci.5b00086

文献信息

• Lipase-mediated desymmetrization of glycerol with aromatic and aliphatic anhydrides
  作者：Daniela I. Batovska、Shuichirou Tsubota、Yasuo Kato、Yasuhisa Asano、Makoto Ubukata

  DOI：10.1016/j.tetasy.2004.09.033

  日期：2004.11

  Chirazyme L-2 (Candida antarctica) catalyzed esterification of glycerol with aromatic and aliphatic anhydrides in 1,4-dioxane is described. All the aromatic monoacylglycerols (MAGs) were produced as (R)-enantiomers, while aliphatic MAGs were obtained either as racemic mixtures or the (S)-enantiomers. The influence of substituted aromatic rings, chain length, and presence of a conjugated double bond in the acyl donor moiety on the enantiotopic selectivity as well as the efficiency of the enzyme was studied. (C) 2004 Elsevier Ltd. All rights reserved.
• Enhanced enantioselectivity of Bacillus coagulans in the hydrolysis of 1,2-O-isopropylidene glycerol esters by thermal knock-out of undesired enzymes
  作者：Diego Romano、Francesco Falcioni、Diego Mora、Francesco Molinari、Andreas Buthe、Marion Ansorge-Schumacher

  DOI：10.1016/j.tetasy.2004.12.021

  日期：2005.2

  The enantioselective hydrolysis of different (RS)-1,2-O-isopropylidene glycerol esters has been achieved with whole cells of Bacillus coagulans NCIMB 9365 furnishing the (S)-alcohol as the major enantiomer. The reaction is catalysed by a thermostable cell-bound carboxylesterase and improvement of the enantioselectivity has been achieved by heat treatment of the whole cells, which causes the knock-outs a non-enantioselective competing enzyme. Thermally-treated cells hydrolysed (RS)-1,2-O-isopropylidene glycerol esters with high enantioselectivity, the highest enantiomeric ratio (80-100) being observed for the benzoate. The biocatalyst displayed good stability and could be re-used after filtration for 12 cycles before showing significant loss of activity; repeated biotransformation batches allowed the recovery of 9.55 g/L of enantiomerically pure (S)-isopropylideneglycerol benzoate starting from 24.0 g/L of the racemic mixture. (C) 2005 Elsevier Ltd. All rights reserved.
• Fischer,E.; Bergmann; Baerwind, Chemische Berichte, 1920, vol. 53, p. 1597
  作者：Fischer,E.、Bergmann、Baerwind

  DOI：——

  日期：——
• KO SOO Y.; MASAMUNE HIROKO; SHARPLESS K. B., J. ORG. CHEM., 52,(1987) N 4, 667-671
  作者：KO SOO Y.、 MASAMUNE HIROKO、 SHARPLESS K. B.

  DOI：——

  日期：——