(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：——
• Selective Monoesterification of Symmetrical Diols Using Resin-Bound Triphenylphosphine
  作者：Gunindra Pathak、Samuel Lalthazuala Rokhum

  DOI：10.1021/acscombsci.5b00086

  日期：2015.9.14

  Coupling reactions to make esters and amides are among the most widely used organic transformations. We report efficient procedures for amide bond formation and for the monoesterification of symmetrical diols in excellent yields without any requirement for high dilution or slow addition using resin-bound triarylphosphonium iodide. Easy purification, low moisture sensitivity, and good to excellent yields

  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。