(aS,R)-6,6'-[(propylene)dioxy]biphenyl-2,2'-diol | 271249-37-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (aS,R)-6,6'-[(propylene)dioxy]biphenyl-2,2'-diol
• 英文别名: (6R,12aS)-6,7-dihydro-6-methyl-dibenzo[e,g][1,4]-dioxocin-1,12-diol；(9R)-9-methyl-8,11-dioxatricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaene-3,16-diol
• CAS: 271249-37-7
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: VIFGFPADOHSMLZ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (aS,R)-6,6'-[(propylene)dioxy]biphenyl-2,2'-diol 在 4,4'-二叔丁基苯并 、 lithium 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (S)-6,6'-hexylenedioxy-2,2'-biphenyldiol
  参考文献：
  名称：

  Asymmetric Desymmetrization of 2,2‘,6,6‘-Tetrahydroxybiphenyl through Annulation with Enantiomerically Pure Bis(mesylate)

  摘要：

  2,2',6,6'-Tetrahydroxybiphenyl undergoes a facile annulation reaction with bis(mesylate) derived from (S)-1,2-propanediol in the presence of Cs2CO3 to give the corresponding asymmetric desymmetrization product of S axial chirality with exclusive diastereoselectivity. The desymmetrization product can be utilized as a versatile chiral building block in asymmetric synthesis of axially chiral 6,6'-disubstituted 2,2'-biphenyldiols.

  DOI：

  10.1021/ol0057840
• 作为产物：
  描述：

  2,2’,6,6’-四氢xy-1,1’-亚苯 、 (S)-methylethylene bis(methanesulfonate) 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (aS,R)-6,6'-[(propylene)dioxy]biphenyl-2,2'-diol
  参考文献：
  名称：

  使用钇-联苯二醇配合物催化 α,β-不饱和酯的不对称环氧化

  摘要：

  我们使用 2-10 mol% 的钇-手性联苯二醇催化剂通过氧化剂的共轭加成成功地进行了 α,β-不饱和酯的催化不对称环氧化反应。多种具有 β-芳基和 β-烷基取代基的底物被有效环氧化，产生相应的 α,β-环氧酯，产率高达 97%，ee 高达 99%。

  DOI：

  10.1021/ja052466t

文献信息

• Tetraoxybiphenyl Ester Chiral Dopants for Cholesteric Liquid Crystal Displays
  申请人：Diehl Donald R.

  公开号：US20120273725A1

  公开（公告）日：2012-11-01

  A liquid crystal composition comprising a chiral dopant compound represented by the following formula: wherein: R1, R2 are independently aryl, alkyl, alkenyl, cycloalkyl, alkoxyaryl, alkaryl or heterocyclic all either substituted or unsubstituted, or combine to form a carbocyclic or heterocyclic ring; R3 and R4 are independently hydrogen, halogen, cyano, alkoxy, NHCOR7, NHSO2R7, COOR7, OCOR7, aryl, alkyl, alkenyl, cycloalkyl, alkoxyaryl, alkaryl or heterocyclic all either substituted or unsubstituted, or combine with either R1 or R2 to form a carbocylic or heterocyclic ring; R5 and R6 are independently hydrogen, CH2, CH, alkyl or aryl either substituted or unsubstituted, COOR7, or combine with L to form a carbocyclic or heterocyclic ring; R7 is aryl, alkyl, alkenyl, cycloalkyl, alkoxyaryl or heterocyclic all either substituted or unsubstituted; L is the non-metallic elements required to form a carbocyclic or heterocyclic ring, or a single bond or a double bond; m is 1-3; n is 0-12.

  一种液晶组合物，包括由以下式表示的手性掺杂剂化合物： 其中：R1，R2独立地为芳基，烷基，烯基，环烷基，烷氧基芳基，烷基芳基或杂环基，均为取代或未取代，或结合形成碳环或杂环；R3和R4独立地为氢，卤素，氰基，烷氧基，NHCOR7，NHSO2R7，COOR7，OCOR7，芳基，烷基，烯基，环烷基，烷氧基芳基，烷基芳基或杂环基，均为取代或未取代，或与R1或R2之一结合形成碳环或杂环；R5和R6独立地为氢，CH2，CH，烷基或芳基，均为取代或未取代，COOR7，或与L结合形成碳环或杂环；R7为芳基，烷基，烯基，环烷基，烷氧基芳基或杂环基，均为取代或未取代；L为形成碳环或杂环所需的非金属元素，或单键或双键；m为1-3；n为0-12。
• New monodentate chiral phosphite ligands for asymmetric hydrogenation
  作者：Peter Hannen、H.-Christian Militzer、Erasmus M. Vogl、Florian A. Rampf

  DOI：10.1039/b306793a

  日期：——

  We report the synthesis of new chiral monodentate phosphite ligands with a biphenyl backbone, the axial chirality of which is introduced early in the synthesis and locked by a chiral alkylenedioxy bridge. We also describe results obtained with these ligands in rhodium-catalysed asymmetric hydrogenation of various substrates.

  我们报道了新型手性单齿膦酸酯配体的合成，该配体具有联苯骨架，其轴向手性在合成早期引入，并通过手性烷基二氧桥固定。我们还描述了这些配体在铑催化下对各种底物进行不对称氢化反应的结果。
• US8691111B2
  申请人：——

  公开号：US8691111B2

  公开（公告）日：2014-04-08
• Catalytic Asymmetric Epoxidation of α,β-Unsaturated Esters Using an Yttrium-Biphenyldiol Complex
  作者：Hiroyuki Kakei、Riichiro Tsuji、Takashi Ohshima、Masakatsu Shibasaki

  DOI：10.1021/ja052466t

  日期：2005.6.1

  We succeeded in a catalytic asymmetric epoxidation reaction of α,β-unsaturated esters via a conjugate addition of an oxidant using 2−10 mol % of the yttirium-chiral biphenyldiol catalyst. A variety of substrates with β-aryl and β-alkyl substituents were epoxidized efficiently, yielding the corresponding α,β-epoxy esters in up to 97% yield and 99% ee.

  我们使用 2-10 mol% 的钇-手性联苯二醇催化剂通过氧化剂的共轭加成成功地进行了 α,β-不饱和酯的催化不对称环氧化反应。多种具有 β-芳基和 β-烷基取代基的底物被有效环氧化，产生相应的 α,β-环氧酯，产率高达 97%，ee 高达 99%。
• Asymmetric Desymmetrization of 2,2‘,6,6‘-Tetrahydroxybiphenyl through Annulation with Enantiomerically Pure Bis(mesylate)
  作者：Toshiro Harada、T. Mai T. Tuyet、Akira Oku

  DOI：10.1021/ol0057840

  日期：2000.5.1

  2,2',6,6'-Tetrahydroxybiphenyl undergoes a facile annulation reaction with bis(mesylate) derived from (S)-1,2-propanediol in the presence of Cs2CO3 to give the corresponding asymmetric desymmetrization product of S axial chirality with exclusive diastereoselectivity. The desymmetrization product can be utilized as a versatile chiral building block in asymmetric synthesis of axially chiral 6,6'-disubstituted 2,2'-biphenyldiols.