dibenzyl 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dibenzyl 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylate
• 英文别名: benzyl 3-hydroxy-4-(2-hydroxy-3-phenylmethoxycarbonylnaphthalen-1-yl)naphthalene-2-carboxylate
• 化学式: C₃₆H₂₆O₆
• 分子量: 554.599
• InChiKey: GJCVTYJWSJQQKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-羟基-3-萘甲酸 在 4-二甲氨基吡啶 、 CuCl(OH)-TMEDA 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 dibenzyl 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylate
  参考文献：
  名称：

  手性 α-氨基膦酸酯作为铜催化 2-萘酚不对称氧化偶联的配体

  摘要：

  具有相邻碳和膦酸酯立体中心的手性 α-氨基膦酸酯已被用作铜催化 2-萘酚氧化偶联的配体，从而以良好的产率和中等至良好的对映体过量生产手性 BINOL。这代表了手性 P 基配体首次应用来实现这种转变。与通常需要复杂的合成工艺来生产手性配体的方法相比，这些手性 α-氨基膦酸酯配体的合成具有显着的优势。

  DOI：

  10.1021/acs.orglett.4c01582

文献信息

• Enantioselective Oxidative Biaryl Coupling Reactions Catalyzed by 1,5-Diazadecalin Metal Complexes:  Efficient Formation of Chiral Functionalized BINOL Derivatives
  作者：Xiaolin Li、J. Brian Hewgley、Carol A. Mulrooney、Jaemoon Yang、Marisa C. Kozlowski

  DOI：10.1021/jo0340206

  日期：2003.7.1

  ligands in the enantioselective oxidative biaryl coupling of substituted 2-naphthol derivatives. Under the optimal conditions employing 2.5-10 mol % of a 1,5-diaza-cis-decalin copper(II) catalyst with oxygen as the oxidant, enantioselective couplings (44-96% ee) could be achieved for a range of 3-substituted 2-naphthols including the ester, ketone, phosphonyl, and sulfonyl derivatives. The relationship

  已经研究了手性的1，5-二氮杂-顺式十氢化萘作为取代的2-萘酚衍生物的对映选择性氧化性联芳基偶联中的配体。在最佳条件下，使用2.5-10 mol％的1,5-二氮杂-顺-十氢化萘铜（II）催化剂，用氧气作为氧化剂，在3-范围内可以实现对映选择性偶联（44-96％ee）取代的2-萘基，包括酯，酮，膦酰基和磺酰基衍生物。萘原料的取代与反应性/选择性之间的关系由几个共同作用的因素决定：（1）取代基对底物氧化电位的影响；
• Highly selective oxidative cross-coupling of 2-naphthol derivatives with chiral copper(I)–bisoxazoline catalysts
  作者：Tomohisa Temma、Shigeki Habaue

  DOI：10.1016/j.tetlet.2005.06.098

  日期：2005.8

  The asymmetric oxidative coupling reaction of 3-hydroxy-2-naphthoate and 2-naphthol derivatives with the CuCl–(S)-(−)-2,2′-isopropylidenebis(4-phenyl-2-oxazoline) catalyst under an O2 atmosphere was carried out. The reaction proceeded in a highly cross-coupling selective manner (⩽99.7%) with a moderate enantioselectivity of up to 65%.

  在O 2下，3-羟基-2-萘甲酸酯和2-萘酚衍生物与CuCl–（S）-（-）-2,2′-亚丙基双（4-苯基-2-恶唑啉）催化剂的不对称氧化偶联反应进行气氛。反应以高度交叉偶联的选择性方式（⩽99.7％）进行，中度对映选择性高达65％。
• In-depth structure–selectivity investigations on asymmetric, copper-catalyzed oxidative biaryl coupling in the presence of 5-cis-substituted prolinamines
  作者：Felix Prause、Benjamin Arensmeyer、Benjamin Fröhlich、Matthias Breuning

  DOI：10.1039/c4cy01676a

  日期：——

  Copper complexes of 5-cis-substituted prolinamines provided up to 87% ee in the enantioselective oxidative biaryl coupling of 3-hydroxy-2-naphthoates.

  5-cis-取代脯氨酸铜配合物在3-羟基-2-萘酸的对映选择性氧化偶联反应中提供高达87%的对映选择性。
• Catalytic asymmetric synthesis of binaphthol derivatives by aerobic oxidative coupling of 3-hydroxy-2-naphthoates with chiral diamine-copper complex
  作者：Makoto Nakajima、Kumiko Kanayama、Irie Miyoshi、Shun-ichi Hashimoto

  DOI：10.1016/0040-4039(95)02063-2

  日期：1995.12

  Asymmetric aerobic oxidative coupling of 3-hydroxy-2-naphthoate with a copper complex prepared in situ from chiral diamine 3 and cuprous chloride as catalyst afforded binaphthol derivatives in good enantioselectivities up to 73% ee.

  3-羟基-2-萘甲酸与由手性二胺3和氯化亚铜作为催化剂原位制备的铜配合物的不对称需氧氧化偶联，提供了对映体选择性高达73％ee的二萘酚衍生物。
• Enantioselective Synthesis of Binaphthol Derivatives by Oxidative Coupling of Naphthol Derivatives Catalyzed by Chiral Diamine·Copper Complexes
  作者：Makoto Nakajima、Irie Miyoshi、Kumiko Kanayama、Shun-ichi Hashimoto、Masahiro Noji、Kenji Koga

  DOI：10.1021/jo981808t

  日期：1999.4.1

  A highly efficient process of aerobic oxidative coupling of 2-naphthol derivatives catalyzed by 1 mol % of Cu(OH)Cl.TMEDA has been developed, Enantioselective oxidative coupling of naphthols was achieved by the use of 10 mol % of chiral catalysts prepared from proline-derived diamines and cuprous chloride, affording the corresponding binaphthols in good enantioselectivities of up to 78% ee. The ester moiety at the 3-position of the substrate was found to be essential for the good asymmetric induction observed in the present coupling reaction.