(2,2-diphenyl-1,3-dioxolan-4-yl)methanol | 131866-04-1

• 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-diphenyl-1,3-dioxolan-4-yl)methanol
• 英文别名: 2,2-Diphenyl-1,3-dioxolane-4-methanol
• CAS: 131866-04-1
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: WCYJCRIYOMOUOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2,2-diphenyl-1,3-dioxolan-4-yl)methanol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 17.08h， 生成 methyl (2,3-syn, 2,4-anti)-2-((hydroxy)(2,2-diphenyl-1,3-dioxolan-4-yl)methyl)but-3-enoate
  参考文献：
  名称：

  Total Regio- and Diastereocontrol in the Aldol Reactions of Dienolborinates

  摘要：

  It is reported that appropriate dienolborinates can provide access to both diastereomers of 2-(hydroxymethyl)but-3-enoates through exclusive alpha-regiocontrol in a non-vinylogous pathway. Contrary to previous reports in which dialkylchloroboranes failed to enolize propanoates, acidity-enhanced but-3-enoates readily undergo enolization, offering unprecedented control over the formation of these valuable synthons. The first example of an aldol reaction in the presence of a phosphine-borane adduct is also reported.

  DOI：

  10.1021/ol400381q
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (2,2-diphenyl-1,3-dioxolan-4-yl)methanol
  参考文献：
  名称：

  Organocatalytic kinetic resolution of racemic primary alcohols using a chiral 1,2-diamine derived from (S)-proline

  摘要：

  A highly efficient and good enantioselective organocatalytic asymmetric acylation of racemic primary alcohols with acyl chlorides has been achieved catalyzed by a chiral 1,2-diamine derived from (S)-proline. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.034

文献信息

• Indium(III) triflate catalysed transacetalisation reactions of diols and triols under solvent-free conditions
  作者：Brendan M. Smith、Tomasz M. Kubczyk、Andrew E. Graham

  DOI：10.1016/j.tet.2012.07.048

  日期：2012.9

  acetals and ketals undergo transacetalisation in the presence of catalytic quantities of indium(III) triflate (In(OTf)3) and diols or triols under solvent-free conditions to generate the corresponding cyclic acetals and ketals in excellent yield. The methodology has been further developed to encompass a tandem acetalisation-acetal exchange protocol, which provides a facile and high yielding route to cyclic

  在无溶剂条件下，在催化量的三氟甲磺酸铟（III）（In（OTf）3）和二醇或三醇的存在下，无环缩醛和缩酮进行反缩醛化，从而以优异的产率生成相应的环状缩醛和缩酮。进一步开发了该方法，以涵盖串联缩醛化-缩醛交换方案，该方案在非常温和的反应条件下提供了一种从非反应性酮向环状缩酮的简便且高收率的途径。
• Synthesis of Amines from Alcohols in a Nonepimerizing One-Pot Sequence - Synthesis of Bioactive Compounds: Cinacalcet and Dexoxadrol
  作者：Claire Guérin、Véronique Bellosta、Gérard Guillamot、Janine Cossy

  DOI：10.1002/ejoc.201200171

  日期：2012.5

  A general, mild, and chemoselective one-pot oxidation/imine-iminium formation/nucleophilic addition sequence allowing the N-alkylation of amines by alcohols is described. This metal-free, one-pot sequence produced a wide variety of amines in good yields and diastereoselectivities, without the epimerization of the enantioenriched amines or alcohols involved in the process. This method was applied to

  描述了一种通用的、温和的、化学选择性的一锅氧化/亚胺-亚胺盐形成/亲核加成序列，允许通过醇对胺进行 N-烷基化。这种不含金属的一锅法以良好的收率和非对映选择性生产了多种胺，而该过程中没有对映体富集的胺或醇的差向异构化。该方法被应用于生物活性化合物西那卡塞和右氧雄酮的合成。
• Structure–Activity Relationships of WOx-Promoted TiO2–ZrO2 Solid Acid Catalyst for Acetalization and Ketalization of Glycerol towards Biofuel Additives
  作者：Mallesham Baithy、Deboshree Mukherjee、Agolu Rangaswamy、Benjaram M. Reddy

  DOI：10.1007/s10562-021-03733-2

  日期：2022.5

  TiO2–ZrO2 solid acid catalyst was prepared and applied in the catalytic acetalization and ketalization of glycerol with carbonyl compounds to produce biofuel additives. The presence of WOx promoter and TiO2 remarkably improved the catalytic activity of ZrO2. Approximately, 100% glycerol conversion was evidenced with non-bulky aliphatic aldehydes and ketones like, propanol and cyclohexanone. The physical

  摘要 制备了WO x促进的TiO 2 -ZrO 2固体酸催化剂，并将其应用于甘油与羰基化合物的催化缩醛化和缩酮化生产生物燃料添加剂。WO x助剂和TiO 2的存在显着提高了ZrO 2的催化活性。大约 100% 的甘油转化被非大体积脂肪醛和酮（如丙醇和环己酮）证明。WO x促进的TiO 2 -ZrO 2的物理表征揭示了 ZrO 2的四方晶相的较高形成，超过单斜。总表面酸度和布朗斯台德与路易斯酸性位点浓度之比分别通过 NH 3 -TPD 和吡啶化学吸附 FTIR 光谱测定。在 WO x促进的TiO 2 -ZrO 2催化剂表面上证明了明显更高浓度的路易斯酸性位点，约 213.29 μmol/gm 。催化活性研究揭示了表面路易斯酸性位点浓度与催化剂活性之间的直接相关性。这一重要观察表明路易斯酸性位点在该催化过程中的关键作用。WO x促进的TiO 2 –ZrO 2催化剂也相当稳定，在甘油与其他取代羰
• Effect of substituent on the enantioselectivity for lipase-catalyzed kinetic resolution of glycerol derivatives
  作者：Yasuhiro Kawanami、Akira Honnma、Kayo Ohta、Naoko Matsumoto

  DOI：10.1016/j.tet.2004.10.107

  日期：2005.1

  The lipase-catalyzed transesterifications of various substituted diphenyl 1,2-ketals of glycerol have been investigated. Efficient modification of the substrate structure with bis(4-bromophenyl) ketal was found to enhance the enantioselectivity up to E=57 at 0 °C.

  已经研究了甘油的各种取代的二苯基1，2-缩酮的脂肪酶催化的酯交换反应。发现使用双（4-溴苯基）缩酮有效修饰底物结构可在0°C时提高对映选择性至E = 57。
• Highly Regioselective Preparation of 1,3-Dioxolane-4-methanol Derivatives from Glycerol Using Phosphomolybdic Acid
  作者：Nitin Fadnavis、Reddipalli Gowrisankar、Gadupudi Ramakrishna、Mithilesh Mishra、Gurrala Sheelu

  DOI：10.1055/s-0028-1083319

  日期：2009.2

  Phosphomolybdic acid (PMA) forms a blue-colored complex with glycerol in a 1:10 molar ratio. The glycerolato complex catalyzes conversion of glycerol into 1,3-dioxolane-4-meth­anol derivatives with complete regiospecificity in high yields (>95%) and the catalyst can be recycled up to ten times without loss of activity or regiospecificity. glycerol - phosphomolybdic acid - complexation - regiospecificity

  磷钼酸（PMA）与甘油以1:10的摩尔比形成蓝色络合物。甘油络合物以高产率（> 95％）催化甘油转化为具有完全区域专一性的1,3-二氧戊环-4-甲醇衍生物，并且该催化剂可循环使用十次而不会损失活性或区域专一性。 甘油-磷钼酸-络合-区域特异性-1,3-二氧戊环-4-甲醇