(1R,2R)-(-)-1-(4-methoxyphenyl)propane-1,2-diol | 166735-89-3

• 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: (1R,2R)-(-)-1-(4-methoxyphenyl)propane-1,2-diol
• 英文别名: (1R,2R)-1-(4-methoxy-phenyl)-propane-1,2-diol；(R,R)-(-)-1-(4-methoxyphenyl)-1,2-ethanediol；1-(4-methoxyphenyl)propane-1,2-diol；1-anisyl-propan-1R,2R-diol；(1'R,2'R)-anethole glycol；(R,R)-anetholediol；(1R,2R)-1-(4-methoxyphenyl)propane-1,2-diol
• CAS: 166735-89-3
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: MRDZSBVJWOXBRW-XCBNKYQSSA-N

物化性质

• 沸点：
  341.0±32.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R)-(-)-1-(4-methoxyphenyl)propane-1,2-diol 在 lithium iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 生成 (4R,5R)-3-Benzoyl-4-(4-methoxy-phenyl)-5-methyl-oxazolidin-2-one
  参考文献：
  名称：

  Expanding Synthetic Utilities of Asymmetric Dihydroxylation Reaction:  Conversion of syn-Diols to syn-Amino Alcohols

  摘要：

  DOI：

  10.1021/jo991079x
• 作为产物：
  描述：

  茴香烯 在 sodium hydroxide 、 (bicyclo[2.2.1]hepta-2,5-diene)-(2,4-pentanedionato)-rhodium 、 双氧水 、 1-(2-二苯基庚基1萘酚)硫酸甲基酯 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 (1R,2R)-(-)-1-(4-methoxyphenyl)propane-1,2-diol
  参考文献：
  名称：

  Rhodium-Catalyzed Enantioselective Diboration of Simple Alkenes

  摘要：

  Enantioselective catalytic reactions that operate directly on inexpensive unactivated alkenes are extraordinarily useful for the preparation of chiral organic building blocks and new materials. While a number of such processes have been developed, our ability to meet the intensifying demand for inexpensive stereochemically complex materials will require a significant expansion of practical catalytic asymmetric reaction methodology. In this regard, the rhodium-catalyzed enantioselective diboration reaction has been developed in order to address a number of extant problems in catalytic alkene transformation simultaneously. This process provides an enantiomerically enriched reactive dimetalated intermediate which can be converted to a variety of difunctional reaction products.

  DOI：

  10.1021/ja035851w

文献信息

• A General and Nonempirical Approach to the Determination of the Absolute Configuration of 1-Aryl-1,2-diols
  作者：Stefano Superchi、Daniele Casarini、Carmela Summa、Carlo Rosini

  DOI：10.1021/jo035803u

  日期：2004.3.1

  coupling method, to assign the absolute configuration of the benzylic stereogenic center of 1-aryl-1,2-diols. According to this method, it is only necessary to prepare the 4-biphenylboronic esters of the diols and to record their CD spectra in the 230−300 nm range, i.e., in the range corresponding to the long-axis 1La transition of the biphenyl chromophore. From the sign of the CD couplet or Cotton effect

  我们在此基于激子偶联方法描述一种简单，通用且可靠的非经验方法，以分配1-芳基-1,2-二醇的苄基立体异构中心的绝对构型。根据该方法，仅需制备二醇的4-联苯硼酸酯并记录其在230-300 nm范围内（即在对应于长轴1 L a的范围内）的CD光谱联苯发色团的过渡。从260 nm处的CD偶联或棉花效应的征兆，可以知道由芳基和联苯发色团跃迁定义的手性，然后确定苄基碳的绝对构型。通过这种方法，已经制定了简单的规则，使我们能够建立许多种类的1-芳基-1，2-二醇的绝对构型。
• [EN] CATALYZED ENANTIOSELECTIVE TRANSFORMATION OF ALKENES<br/>[FR] TRANSFORMATION ENANTIO-SELECTIVE CATALYSEE D'ALCENES
  申请人：UNIV NORTH CAROLINA

  公开号：WO2005012209A3

  公开（公告）日：2005-08-11
• Rh-Catalyzed Enantioselective Diboration of Simple Alkenes:  Reaction Development and Substrate Scope
  作者：Stéphane Trudeau、Jeremy B. Morgan、Mohanish Shrestha、James P. Morken

  DOI：10.1021/jo051651m

  日期：2005.11.1

  The rhodium-catalyzed reaction between bis(catecholato)diboron and simple alkenes results in the syn addition of the diboron across the alkene. The resulting 1,2-bis(boronate) is subsequently oxidized to provide the 1,2-diol. In the presence of enantiomerically enriched Quinap ligand, high enantioselection in the diboration can be achieved. The reaction is highly selective for trans- and trisubstituted alkenes and can be selective for some monosubstituted alkenes as well. The development of this reaction is described as is the substrate scope and experiments that are informative about the reaction mechanism and competing pathways.
• Determination of the Absolute Configuration of 1-Arylethane-1,2-diols by a Nonempirical Analysis of the CD Spectra of Their 4-Biphenylboronates
  作者：Stefano Superchi、Maria Irene Donnoli、Carlo Rosini

  DOI：10.1021/ol991146+

  日期：1999.12.1

  [GRAPHICS]1-Arylethane-1,2-diols 1, reacting with 4-biphenylboronic acid 2, form the conformationally defined boronates 3 where the aryl and biphenyl chromophores assume a fixed and known relative disposition. These chromophores thus define an exciton coupled system, whose chirality (revealed by the sign of the biphenyl On band at 260 nm) allows an unambiguous assignment of the absolute configuration of the stereogenic center. This approach provides the hitherto unreported absolute configuration of diols 1c-f.
• Enantio- and Diastereoselective Synthesis of 1,2-Hydroxyboronates through Cu-Catalyzed Additions of Alkylboronates to Aldehydes
  作者：Matthew V. Joannou、Brandon S. Moyer、Simon J. Meek

  DOI：10.1021/jacs.5b03477

  日期：2015.5.20

  The first catalytic enantio- and diastereoselective synthesis of 1;2-hydroxyboronates is reported. Reactions are promoted by a readily available chiral monodentate phosphoramidite copper complex in the presence of an alkyl 1,1-diboron reagent. Products contain two contiguous stereogenic centers and are obtained in up to 91% yield, >98:2 d.r., arid 98:2 e.r. The reaction is tolerant of aryl and vinyl aldehydes, and the 1,2-hydroxyboronate products can be transformed into versatile derivatives. Mechanistic experiments indicate control of absolute stereochemistry of the alpha-boryl component.