(4R,5R)-2,2-diphenyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester | 146499-09-4

• 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: (4R,5R)-2,2-diphenyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester
• 英文别名: 2,2-diphenyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester；dimethyl (4R,5R)-2,2-diphenyl-1,3-dioxolane-4,5-dicarboxylate；(4R,5R)-2,2-diphenyl-4,5-bis(methoxycarbonyl)-1,3-dioxolane；(4R,5R)-2,2-diphenyl-4,5-dimethoxycarbonyl-1,3-dioxolane；(R,R)-dimethyl-O,O-(diphenylmethylidene)tartrate
• CAS: 146499-09-4
• 化学式: C₁₉H₁₈O₆
• 分子量: 342.348
• InChiKey: JHOLMNFBANTORU-HZPDHXFCSA-N

物化性质

• 沸点：
  442.4±40.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R,5R)-2,2-diphenyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester 在 水 、 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.17h， 以100%的产率得到(R,R)-2,2-diphenyl-[1,3]dioxolane-4,5-dicarboxylic acid
  参考文献：
  名称：

  Cyclic Ketals of Tartaric Acid: Simple and Tunable Reagents for the Determination of the Absolute Configuration of Primary Amines

  摘要：

  2,2-Diphenyl-[1,3]dioxolane-4,5-dicarboxylic acid (DPD) and 2,2-dinaphthalen-2-yl-[1,3]dioxolane-4,5-dicarboxylic acid (DND) have been synthesized starting from dimethyl tartrate. DPD and DND amides of alpha-chiral primary amines showed significantly different H-1 chemical shift values depending on the stereochemistry of the derivatizing agent. On the basis of this chemical shift difference, the absolute configuration of amine substrates could be assigned. DND amides showed significantly larger chemical shift differences than the corresponding DPD amides allowing for a more error-free assignment.

  DOI：

  10.1021/ol902942k
• 作为产物：
  描述：

  L-(+)-酒石酸二甲酯 、 苯甲酮二甲基缩酮 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以60%的产率得到(4R,5R)-2,2-diphenyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  手性布朗斯台德酸介导的对映选择性光环加成反应：Rocaglamides 的不对称合成

  摘要：

  罗卡格酸甲酯和相关天然产物罗卡格莱胺和罗卡格洛尔的对映选择性合成概述。该方法涉及由手性布朗斯台德酸 (TADDOL) 促进的对映选择性 [3 + 2] 光环加成反应，以提供 aglain 前体，然后是酮醇转移/还原序列到 rocaglate 核心。

  DOI：

  10.1021/ja062621j

文献信息

• Enantioselective Photocycloaddition Mediated by Chiral Brønsted Acids:  Asymmetric Synthesis of the Rocaglamides
  作者：Baudouin Gerard、Sheharbano Sangji、Daniel J. O'Leary、John A. Porco

  DOI：10.1021/ja062621j

  日期：2006.6.1

  Enantioselective syntheses of methyl rocaglate and the related natural products rocaglamide and rocaglaol are outlined. The approach involves enantioselective [3 + 2] photocycloaddition promoted by chiral Brønsted acids (TADDOLs) to afford an aglain precursor followed by a ketol shift/reduction sequence to the rocaglate core.

  罗卡格酸甲酯和相关天然产物罗卡格莱胺和罗卡格洛尔的对映选择性合成概述。该方法涉及由手性布朗斯台德酸 (TADDOL) 促进的对映选择性 [3 + 2] 光环加成反应，以提供 aglain 前体，然后是酮醇转移/还原序列到 rocaglate 核心。
• Seebach, Dieter; Beck, Albert K.; Dahinden, Robert, Croatica Chemica Acta, 1996, vol. 69, # 2, p. 459 - 484
  作者：Seebach, Dieter、Beck, Albert K.、Dahinden, Robert、Hoffmann, Matthias、Kuehnle, Florian N. M.

  DOI：——

  日期：——
• On the origin of changes in topicity observed in Diels–Alder reactions catalyzed by Ti–TADDOLates
  作者：Belén Altava、M.Isabel Burguete、Eduardo Garcı́a-Verdugo、Santiago V. Luis、Juan F. Miravet、Marı́a J. Vicent

  DOI：10.1016/s0957-4166(00)00464-x

  日期：2000.12

  New C-2 symmetric TADDOLs containing different groups at the 2-position of the dioxolane ring have been prepared. The Ti catalysts derived from these have been studied in the Diels-Alder reaction of cyclopentadiene and (E)-2-butenoyl-1,3-oxazolidin-2-one. Substituents at the C-2 position of the dioxolane ring can play an important role in determining the selectivity as well as the nature of the major isomer. This effect is more important for TADDOLs containing bulky aromatic groups such as 3,5-dimethylphenyl- or 1-naphthyl at the alpha -positions. Experimental evidence supports the hypothesis that pi-pi. interactions between aromatic groups at the C-2 and the ones at the a-positions are critical in this respect. (C) 2001 Elsevier Science Ltd. All rights reserved.
• TADDOL-TiCl2 catalyzed Diels-Alder reactions: unexpected influence of the substituents in the 2-position of the dioxolane ring on the stereoselectivity
  作者：Belén Altava、Ma Isabel Burguete、JoséM. Fraile、JoséI. García、Santiago V. Luis、JoséA. Mayoral、Ana J. Royo、María J. Vicent

  DOI：10.1016/s0957-4166(97)00264-4

  日期：1997.8

  Several alpha,alpha,alpha',alpha'-tetra(3,5-dimethylphenyl)-1,3-dioxolane-4,5-demethanols have been synthesized, and their TiCl2 derivatives used as catalysts in the reaction of cyclopentadiene with (E)-2-butenoyl-1,3-oxazolidin-2-one. The substituents in the 2-position of the dioxolane ring exert a decisive influence on the extent and direction of the asymmetric induction and, consequently any possible enantiomer of the cycloadducts can be preferentially obtained by changing these substituents. Molecular mechanics calculations of the structures and relative energies of the possible dienophile-catalyst complexes offer a tentative explanation for the results described. (C) 1997 Elsevier Science Ltd.
• Highly Enantioselective Protonation of the 3,4-Dihydro-2- methylnaphthalen-1(2H)-one Li-Enolate by TADDOLs
  作者：Ana Cuenca、Mercedes Medio-Simón、Gregorio Asensio Aguilar、Daniel Weibel、Albert K. Beck、Dieter Seebach

  DOI：10.1002/1522-2675(20001220)83:12<3153::aid-hlca3153>3.0.co;2-r

  日期：2000.12.20