(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-phenylacetate | 111219-29-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-phenylacetate
• 英文别名: (2,2-dimethyl-1,3-dioxolane-4-yl)methyl phenylacetate；(RS)-1,2-O-isopropylidene glycerol phenylacetate；(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl phenylacetate
• CAS: 111219-29-5
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: GUFKXOMWPLXIAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  338.7±27.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-phenylacetate 生成 (S)-(+)-1,2-异亚丙基甘油
  参考文献：
  名称：

  FUGANTI, GLAUDIO;GRASSELLI, PIERO;SERVI, STEFANO;LAZZARINI, AMERIGA;CASAT+, TETRAHEDRON, 44,(1988) N 9, 2575-2582

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酰氯 、 丙酮缩甘油 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以81%的产率得到(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-phenylacetate
  参考文献：
  名称：

  Synthesis of glycerolipids containing simple linear acyl chains or aromatic rings and evaluation of their Mincle signaling activity

  摘要：

  合成的甘油酯衍生物具有简单的烷基链，可刺激与先天性免疫系统相关的 Mincle 介导的信号检测。

  DOI：

  10.1039/c8cc07322h

文献信息

• Substrate specificity and enantioselectivity of penicillinacylase catalyzed hydrolysis of phenacetyl esters of synthetically useful carbinols
  作者：Claudio Fuganti、Piero Grasselli、Stefano Servi、Ameriga Lazzarini、Paolo Casati

  DOI：10.1016/s0040-4020(01)81708-7

  日期：1988.1

  Penicillinacylase from , immoblized on Eupergit C beads catalyzes the hydrolysis in water/CH3CN 10:1, at pH 7.5 and 23° C, of a set of O-phenylacetate esters of primary carbinols. The highest enantioselectivity is observed in the case of the 2,2-dimethyl-1,3-dioxolane-4-methanols structurally related to the penicillin (1) framework. Minor modifications of this basic structure are not altering the acceptability

  固定在Eupergit C珠上的青霉素酰化酶催化在水/ CH 3 CN 10：1中在pH 7.5和23°C下水解一系列邻苯甲醇的邻苯乙酸酯。在与青霉素（1）骨架结构相关的2,2-二甲基-1,3-二氧戊环-4-甲醇中观察到最高的对映选择性。对这种基本结构的微小修饰不会改变酶的可接受性，但会显着降低水解的对映选择性，就像使用苯作为溶剂和与琼脂糖结合的酶一样。
• Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate Methodology
  作者：Zachary J. Struzik、Shruti Biyani、Tim Grotzer、Judith Storch、David H. Thompson

  DOI：10.3390/molecules27072199

  日期：——

  Naturally occurring phospholipids, such as phosphatidyl glycerol (PG), are gaining interest due to the roles they play in disease mechanisms. To elucidate the metabolism of PG, an optically pure material is required, but this is unfortunately not commercially available. Our previous PG synthesis route utilized phosphoramidite methodology that addressed issues surrounding fatty acid substrate scope

  天然存在的磷脂，如磷脂酰甘油 (PG)，因其在疾病机制中发挥的作用而受到关注。为了阐明 PG 的代谢，需要一种光学纯材料，但不幸的是，这种材料无法在市场上买到。我们之前的 PG 合成路线使用亚磷酰胺方法，解决了在头基磷酸化之前围绕脂肪酸底物范围和甘油主链修饰的问题，但由于纯化挑战，整个途径的可重复性步履蹒跚。在此，我们利用具有色谱友好且稳定的三乙基铵 H-膦酸盐的 H-膦酸盐，提出了一种通过更少的步骤获得光学纯 PG 的稳健途径。我们的路线也适用于同时安装不同的酰基链，
• 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.
• FUGANTI C.; GRASSELLI P.; SERVI S.; LAZZARINI A.; CASATI P., J. CHEM. SOC. CHEM. COMMUN.,(1987) N 8, 538-539
  作者：FUGANTI C.、 GRASSELLI P.、 SERVI S.、 LAZZARINI A.、 CASATI P.

  DOI：——

  日期：——