3,3'-dichloro-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene | 142010-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,3'-dichloro-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene
• 英文别名: 3,3'-Dichloro-2,2'-bis-methoxymethoxy-[1,1']binaphthalenyl；1,1'-Binaphthalene, 3,3'-dichloro-2,2'-bis(methoxymethoxy)-, (A+/-)-；3-chloro-1-[3-chloro-2-(methoxymethoxy)naphthalen-1-yl]-2-(methoxymethoxy)naphthalene
• CAS: 142010-86-4
• 化学式: C₂₄H₂₀Cl₂O₄
• 分子量: 443.326
• InChiKey: IYLDXLOFDXOWGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3'-dichloro-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以69 %的产率得到(R)-3,3'-dichloro-1,1'-binaphthalene-2,2'-diol
  参考文献：
  名称：

  HAT Catalysts to Facilitate Acid Mediated Cleavage of Biaryl C–C Bonds in Binaphthols

  摘要：

  DOI：

  10.1021/acs.orglett.2c03325
• 作为产物：
  描述：

  rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 在 正丁基锂 、 六氯乙烷 作用下， 生成 3,3'-dichloro-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene
  参考文献：
  名称：

  Expedient route to 3- and 3,3′-substituted 1,1′-bi-2-naphthols by directed ortho metalation and suzuki cross coupling methods

  摘要：

  A directed ortho metalation-based route to 3- and 3,3'-substituted binaphthols 2a-c and 3a-c, including chiral materials, is described. Using the Suzuki cross coupling process, dibromo system 3a (E = Br) has been transformed into 3,3'-diaryl binaphthols 5.

  DOI：

  10.1016/s0040-4039(00)74182-7

文献信息

• Pd-Catalyzed Cross-Coupling of Aryllithium Reagents with 2-Alkoxy-Substituted Aryl Chlorides: Mild and Efficient Synthesis of 3,3′-Diaryl BINOLs
  作者：Luis M. Castelló、Valentín Hornillos、Carlos Vila、Massimo Giannerini、Martín Fañanás-Mastral、Ben L. Feringa

  DOI：10.1021/ol5032409

  日期：2015.1.2

  Palladium-catalyzed cross-coupling of aryllithium reagents with 2-alkoxy-substituted aryl chlorides is described. The reactions proceed under mild conditions with short reaction times and provide a wide range of 2-alkoxy-substituted biaryls. This new methodology is applied to the efficient preparation of 3,3′-diaryl BINOLs and represents the first synthesis of this important class of chiral compounds

  描述了钯催化的芳基锂试剂与 2-烷氧基取代的芳基氯化物的交叉偶联。该反应在温和条件下进行，反应时间短，并提供范围广泛的 2-烷氧基取代的联芳基化合物。这种新方法应用于 3,3'-二芳基 BINOL 的有效制备，代表了从相应的 3,3'-二氯 BINOL 合成这类重要手性化合物的首次。
• Binaphthol-Catalyzed Asymmetric Conjugate Arylboration of Enones
  作者：Heather M. Turner、Jignesh Patel、Nootaree Niljianskul、J. Michael Chong

  DOI：10.1021/ol202391r

  日期：2011.11.4

  Conjugate addition of arylboronates to alpha,beta-unsaturated ketones may be catalyzed by chiral binaphthols with enantioselectivities of up to 99:1. Best results were observed with 3,3'-dichloro-BINOL. This chemistry was applied to syntheses of intermediates for syntheses of (+)-indatraline and (+)-tolterodine.
• Expedient route to 3- and 3,3′-substituted 1,1′-bi-2-naphthols by directed ortho metalation and suzuki cross coupling methods
  作者：Paul J. Cox、Wei Wang、Victor Snieckus

  DOI：10.1016/s0040-4039(00)74182-7

  日期：1992.4

  A directed ortho metalation-based route to 3- and 3,3'-substituted binaphthols 2a-c and 3a-c, including chiral materials, is described. Using the Suzuki cross coupling process, dibromo system 3a (E = Br) has been transformed into 3,3'-diaryl binaphthols 5.
• HAT Catalysts to Facilitate Acid Mediated Cleavage of Biaryl C–C Bonds in Binaphthols
  作者：Christopher A. Sojdak、Marisa C. Kozlowski

  DOI：10.1021/acs.orglett.2c03325

  日期：2022.11.18