2'-hydroxy-[1,1'-binaphthalen]-2-yl 2-phenylacetate | 173828-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2'-hydroxy-[1,1'-binaphthalen]-2-yl 2-phenylacetate
• 英文别名: [1-(2-Hydroxynaphthalen-1-yl)naphthalen-2-yl] 2-phenylacetate
• CAS: 173828-17-6
• 化学式: C₂₈H₂₀O₃
• 分子量: 404.465
• InChiKey: DOJSCIVVSIFLHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2'-hydroxy-[1,1'-binaphthalen]-2-yl 2-phenylacetate 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 四氯化钛 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (-)-(2R,3R)-2-(4-methoxyphenyl)-3-phenyl-1,4-butanediol
  参考文献：
  名称：

  Asymmetric C C bond formation by the mixed oxidative coupling of 1,1′-bi-2-naphthyl esters

  摘要：

  Asymmetric C-C bond formation was effected by the oxidative coupling of two different ester enolates using (R)-(+)-1,1'-bi(2-naphthol) as a common tether which served to link together both ester moieties in an asymmetric environment. Reduction of the corresponding succinates afforded diastereomerically pure 2,3-disubstituted-1,4-butanediols. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00173-8
• 作为产物：
  描述：

  苯乙酸 、 (R)-1,1'-Bi-2-naphthol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到2'-hydroxy-[1,1'-binaphthalen]-2-yl 2-phenylacetate
  参考文献：
  名称：

  Asymmetric C C bond formation by the mixed oxidative coupling of 1,1′-bi-2-naphthyl esters

  摘要：

  Asymmetric C-C bond formation was effected by the oxidative coupling of two different ester enolates using (R)-(+)-1,1'-bi(2-naphthol) as a common tether which served to link together both ester moieties in an asymmetric environment. Reduction of the corresponding succinates afforded diastereomerically pure 2,3-disubstituted-1,4-butanediols. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00173-8

文献信息

• Isothiourea‐Catalysed Regioselective Acylative Kinetic Resolution of Axially Chiral Biaryl Diols
  作者：Shen Qu、Mark D. Greenhalgh、Andrew D. Smith

  DOI：10.1002/chem.201805631

  日期：2019.2.21

  An operationally simple isothiourea‐catalysed acylative kinetic resolution of unprotected 1,1′‐biaryl‐2,2′‐diol derivatives has been developed to allow access to axially chiral compounds in highly enantioenriched form (s values up to 190). Investigation of the reaction scope and limitations provided three key observations: i) the diol motif of the substrate was essential for good conversion and high

  已开发出一种操作简单的异硫脲催化的未保护的1,1'-联芳基-2,2'-二醇衍生物的酰基动力学拆分，可使用高度对映体富集形式的轴向手性化合物（s值高达190）。对反应范围和限制的研究提供了三个关键的观察结果：i）底物的二醇基序对于良好的转化率和高s值是必不可少的；ii）所述使用的α，α-二取代的混合酸酐（2,2-二苯乙酸新戊酸酐）对于最大程度地减少二酰化并提供高选择性至关重要。iii）二醇的3,3'-位上存在取代基阻碍了有效的酰化作用。该最终观察结果用于具有单个3-取代基的不对称联芳基二醇底物的高度区域选择性酰基动力学动力学拆分。基于确定的关键观察结果，提出了酰化过渡态模型来解释该动力学拆分的对映选择性。
• Diastereoselective reactions of 1,1′-binaphthyl ester enolates with carbonyl electrophiles
  作者：Mija Ahn、Kiyoshi Tanaka、Kaoru Fuji

  DOI：10.1039/a706673b

  日期：——

  Diastereoselectivity in the aldol and the conjugate additions of 2′-hydroxy-1,1′-binaphthyl ester enolates with a variety of carbonyl electrophiles has been examined. The ester enolate generated by BuLi reacts with several aldehydes to give the threo products preferentially with high diastereoselectivity and in good yield. Satisfactory diastereoselectivity has also been observed in the minor erythro derivatives. A mechanistic interpretation of the results is made on the basis of the absolute stereochemistry of the products.

  已研究了2′-羟基-1,1′-联萘酯酮烯与多种羰基电烯的醇醛反应和结合加成反应中的二面体选择性。由BuLi生成的酯酮烯与几种醛反应，优先生成threo产物，具有高的二面体选择性和良好的收率。在少量的erythro衍生物中也观察到了令人满意的二面体选择性。根据产物的绝对立体化学，对结果进行了机制解释。
• Complex-induced proximity effects in enolate formation. Highly diastereoselective α-methylation of binaphthyl esters of arylacetic acids.
  作者：Kaoru Fuji、Manabu Node、Fujie Tanaka

  DOI：10.1016/s0040-4039(00)97115-6

  日期：1990.1

  Highly diastereoselective methylation of binaphthyl esters of arylacetic acids and its application to the syntheses of antiinflammatory drugs, (S)- suprofen and (S)-naproxen.

  芳丙酸双萘酯的高度非对映选择性甲基化及其在抗炎药（S）-suprofen和（S）-萘普生的合成中的应用。
• Tanaka, Fujie; Node, Manabu; Tanaka, Kiyoshi, Journal of the American Chemical Society, 1995, vol. 117, # 49, p. 12159 - 12171
  作者：Tanaka, Fujie、Node, Manabu、Tanaka, Kiyoshi、Mizuchi, Maki、Hosoi, Shinzo、Nakayama, Masayo、Taga, Tooru、Fuji, Kaoru

  DOI：——

  日期：——
• Binaphthol as a chiral auxiliary. Asymmetrical alkylation of arylacetic acid
  作者：Kaoru Fuji、Manabu Node、Fujie Tanaka、Shinzo Hosoi

  DOI：10.1016/s0040-4039(00)99135-4

  日期：1989.1