methyl 2,3-dihydroxy-3-(4-methoxyphenyl)propanoate | 106146-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 2,3-dihydroxy-3-(4-methoxyphenyl)propanoate
• CAS: 106146-94-5
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: KPLLZYQROJDPIU-UHFFFAOYSA-N

物化性质

• 沸点：
  381.4±21.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3-dihydroxy-3-(4-methoxyphenyl)propanoate 在 sodium azide 、 lipase Pseudomonas cepacia 、 氢溴酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  脂肪酶催化的酯交换反应是制备高手性顺-1，2-二醇的可行途径。紫杉醇侧链的合成

  摘要：

  syn -2,3-二羟基-3-苯基丙酸甲酯（1a）及其简单衍生物（1b-e）在LPS催化的酯交换反应中得到有效拆分，从而导致紫杉醇侧链及其类似物的合成拆分的对映体。

  DOI：

  10.1016/s0040-4039(98)00147-6
• 作为产物：
  描述：

  Methyl 3-hydroxy-3-(4-methoxyphenyl)-2-oxopropanoate 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 以61%的产率得到methyl 2,3-dihydroxy-3-(4-methoxyphenyl)propanoate
  参考文献：
  名称：

  Ozonolysis of Morita–Baylis–Hillman adducts originated from aromatic aldehydes: an expeditious diastereoselective approach for the preparation of α,β-dihydroxy-esters

  摘要：

  We disclose herein ozonolysis of Morita-Baylis-Hillman adducts originated from aromatic aldehydes. This efficient reaction provides alpha-ketoesters with different substitution patterns on the aromatic ring. Diastercoselective reduction of the corresponding alpha-ketoester obtained in the oxidative cleavage step provides alpha,beta-dihydroxy-esters with excellent degree of anti diastereoselection. The method is simple and easy to execute and is therefore a valuable alternative to prepare either alpha-ketoesters or alpha-dihydroxy-esters. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.149

文献信息

• Sc(OTf)3-catalyzed diastereoselective Friedel–Crafts reactions of arenes and hetarenes with 3-phenylglycidates
  作者：David Wilcke、Thorsten Bach

  DOI：10.1039/c2ob25988e

  日期：——

  Five different para-substituted 3-phenylglycidates (3-phenyloxirane-2-carboxylates) were prepared and subjected to reactions with arenes and hetarenes under Lewis acid catalysis. Sc(OTf)3 was found to effectively (5 mol%) promote a Friedel–Crafts reaction in nitromethane as the solvent. The reaction was shown to proceed stereoconvergently, which makes the intermediacy of a benzylic cation likely. The diastereoselectivities varied depending on the choice of the nucleophile and 3-arylglycidate. Best results were obtained with tert-butyl 3-anisylglycidate, which delivered the respective products with high syn-preference in diastereomeric ratios (d.r.) between 82 : 18 and >95 : 5. The observed selectivity can be explained by a model, according to which the intermediate benzylic cations adopt a preferred conformation, which allows for diastereoface-differentiation by the adjacent stereogenic center.

  制备了五种不同的对位取代3-苯基缩水甘油酸酯（3-苯基环氧乙烷-2-羧酸酯），并使其在Lewis酸催化下与芳烃和杂芳烃反应。发现Sc(OTf)3能有效（5摩尔%）促进以硝基甲烷为溶剂的Friedel-Crafts反应。反应呈现立体汇聚性，这表明可能存在苄基阳离子中间体。对映选择性因亲核试剂和3-芳基缩水甘油酸酯的选择而异。使用叔丁基3-茴香基缩水甘油酸酯时效果最佳，产物的顺-偏好性在外消旋体比例（d.r.）介于82:18至>95:5之间。观察到的选择性可通过一个模型解释，该模型表明中间体苄基阳离子采取的优先构象允许相邻的手性中心进行对映面区分。
• Synthesis of All Stereoisomers and Some Congeners of Isocytoxazone
  作者：Vitomir Šunjić、Zdenko Hameršak、Dragan Šepac、Dinko Žiher

  DOI：10.1055/s-2003-37353

  日期：——

  cis-Isocytoxazone 2a and trans-isocytoxazone 2h, structural isomers of the antiasthmatic agent cytoxazone (-)-1, and their 5-substituted congeners 23-28 have been prepared. Aldol reaction of para-substituted benzaldehydeswith 7-chloro-1-methyl-5-phenyl-1,4-benzodiazepin-2-one, followed by separation of diastereomeric racemates afforded 3-10. Acid-catalyzed 1,4-benzodiazepine ring opening, and transformation

  已制备顺式-异胞嘧啶2a和反式-异胞嘧啶2h，抗哮喘药胞嘧啶(-)-1的结构异构体，以及它们的5-取代同系物23-28。对位取代的苯甲醛与 7-chloro-1-methyl-5-phenyl-1,4-benzodiazepin-2-one 进行羟醛反应，然后分离非对映体外消旋物，得到 3-10。酸催化的 1,4-苯并二氮杂环开环，以及通过 1,3-恶唑烷-2-酮的 4-甲氧基羰基衍生物转化 β-芳基-β-羟基-α-氨基酸 (11-16) 的甲酯(17-22) 和它们的还原提供了目标 oxazolidin-2-one 衍生物 23-28。外消旋异环唑酮 2a 和 2b 由 4-甲氧基苯乙烯环氧化物通过独立路线制备。这些非对映体外消旋体的纯对映体通过 HPLC 色谱在手性固定相上进行分离。
• Fine regioselective tuning in the oxidation of sec,sec 1,2-diols by dimethyldioxirane
  作者：Paolo Bovicelli、Anna Sanetti、Paolo Lupattelli

  DOI：10.1016/0040-4020(96)00615-1

  日期：1996.8

  Non symmetric sec,sec 1.2-diols and their O-isopropylidene derivatives undergo a regioselective oxidation by dimethyldioxirane depending on the electronic effects of the substituents. These results support previous views about the concerted -insertion mechanism via a polar transition state.

  根据取代基的电子效应，不对称的仲，仲1.2-二醇及其O-异亚丙基衍生物会受到二甲基二环氧乙烷的区域选择性氧化。这些结果支持以前关于通过极性过渡状态的协调插入机制的观点。
• Chiral compounds
  申请人：Merck Patent GmbH

  公开号：US06495217B2

  公开（公告）日：2002-12-17

  The invention relates to chiral compounds of formula I wherein R1, R2, X, Y1 and Y2 have the meanings defined herein, as well as to liquid crystalline mixtures comprising at least one chiral compound of formula I. The invention also relates to chiral linear or crosslinked liquid crystalline polymers obtainable by polymerizing a polymerizable mixture comprising at least one chiral compound of formula I, and to the use of chiral compounds of formula I and mixtures and polymers obtained thereof in liquid crystal displays, such as STN, TN, AMD-TN, temperature compensation, guest-host, phase change or surface stabilized or polymer stabilized cholesteric texture (SSCT, PSCT) displays, in active and passive optical elements like polarizers, compensators, alignment layers, color filters or holographic elements in adhesives, synthetic resins with anisotropic mechanical properties, cosmetics, diagnostics, liquid crystal pigments, for decorative and security applications, in nonlinear optics, optical information storage or as chiral dopants, and to a liquid crystal display comprising a mixture comprising at least one chiral compound of formula I.

  该发明涉及式I的手性化合物，其中R1、R2、X、Y1和Y2具有此处定义的含义，以及包含至少一种式I手性化合物的液晶混合物。该发明还涉及通过聚合包含至少一种式I手性化合物的可聚合混合物而可获得的手性线性或交联液晶聚合物，以及在液晶显示器中使用式I手性化合物、混合物和聚合物，例如STN、TN、AMD-TN、温度补偿、客体-宿主、相变或表面稳定或聚合稳定的胆甾醇纹理（SSCT，PSCT）显示器，以及在主动和被动光学元件中，如偏振片、补偿器、取向层、彩色滤光片或全息元件中的使用，还包括在粘合剂、具有各向异性机械性能的合成树脂、化妆品、诊断学、液晶颜料、用于装饰和安全应用、非线性光学、光学信息存储或作为手性掺杂剂，并涉及包含至少一种式I手性化合物的混合物的液晶显示器。
• CHIRAL COMPOUNDS
  申请人：——

  公开号：US20020005505A1

  公开（公告）日：2002-01-17

  The invention relates to chiral compounds of formula I 1 wherein R 1 , R 2 , X, Y 1 and Y 2 have the meanings defined herein, as well as to liquid crystalline mixtures comprising at least one chiral compound of formula I. The invention also relates to chiral linear or crosslinked liquid crystalline polymers obtainable by polymerizing a polymerizable mixture comprising at least one chiral compound of formula I, and to the use of chiral compounds of formula I and mixtures and polymers obtained thereof in liquid crystal displays, such as STN, TN, AMD-TN, temperature compensation, guest-host, phase change or surface stabilized or polymer stabilized cholesteric texture (SSCT, PSCT) displays, in active and passive optical elements like polarizers, compensators, alignment layers, color filters or holographic elements in adhesives, synthetic resins with anisotropic mechanical properties, cosmetics, diagnostics, liquid crystal pigments, for decorative and security applications, in nonlinear optics, optical information storage or as chiral dopants, and to a liquid crystal display comprising a mixture comprising at least one chiral compound of formula I.

  该发明涉及式I1的手性化合物，其中R1，R2，X，Y1和Y2具有所定义的含义，以及至少包含式I的手性化合物的液晶混合物。该发明还涉及通过聚合包含至少一种式I的手性化合物的聚合物可获得手性线性或交联液晶聚合物，以及在液晶显示器（如STN，TN，AMD-TN，温度补偿，客体-主体，相变或表面稳定或聚合稳定胆甾质纹理（SSCT，PSCT）显示器）中使用式I的手性化合物和由此获得的混合物和聚合物，在活性和被动光学元件中，如偏振器、补偿器、定向层、彩色滤光片或全息元件中的粘合剂、具有各向异性机械性能的合成树脂、化妆品、诊断、液晶颜料，用于装饰和安全应用，非线性光学，光学信息存储或作为手性掺杂剂，并涉及包含至少一种式I的手性化合物的混合物的液晶显示器。