7-isopropoxynaphthalen-2-ol | 190434-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-isopropoxynaphthalen-2-ol
• 英文别名: 7-isopropoxy-2-naphthol；7-Propan-2-yloxynaphthalen-2-ol
• CAS: 190434-39-0
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: IWEGNJDRYKQLST-UHFFFAOYSA-N

物化性质

• 沸点：
  351.9±15.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-isopropoxynaphthalen-2-ol 在 1,2-双(二苯基膦)乙烷氯化镍 作用下， 以 吡啶 、 乙醚 为溶剂， 反应 22.5h， 生成 2-isopropyloxy-7-isopropylnaphthalene
  参考文献：
  名称：

  Rapid atropisomerization of 1,1′:5′,1″-ternaphthalene-2,2′,6′,2″-tetrol (TERNOL) and its inhibition by tethering at positions 7 and 7″

  摘要：

  Atropisomerization of 1,1':5',1"-temaphthalene-2,2',6',2"-tetrol (TERNOL) is very fast under basic conditions. The stereochemical instability is attributed to the nature of oxide anion of the central 2,6-naphthodiol moiety. Ring-closing metathesis of 7,7"-diallyloxy TERNOL results in intramolecular tethering in a high yield, which intrinsically inhibits the rapid isomerization. Bidentate sites in the tethered TERNOL are proved to have enough structural flexibility as an axial chiral ligand. (c) 2006 Elsevier Ltd, All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.046
• 作为产物：
  描述：

  2,7-二羟基萘 、 2-溴丙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以43%的产率得到7-isopropoxynaphthalen-2-ol
  参考文献：
  名称：

  Rapid atropisomerization of 1,1′:5′,1″-ternaphthalene-2,2′,6′,2″-tetrol (TERNOL) and its inhibition by tethering at positions 7 and 7″

  摘要：

  Atropisomerization of 1,1':5',1"-temaphthalene-2,2',6',2"-tetrol (TERNOL) is very fast under basic conditions. The stereochemical instability is attributed to the nature of oxide anion of the central 2,6-naphthodiol moiety. Ring-closing metathesis of 7,7"-diallyloxy TERNOL results in intramolecular tethering in a high yield, which intrinsically inhibits the rapid isomerization. Bidentate sites in the tethered TERNOL are proved to have enough structural flexibility as an axial chiral ligand. (c) 2006 Elsevier Ltd, All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.046

文献信息

• Peptide‐Catalyzed Fragment Couplings that Form Axially Chiral Non‐ <i> C ₂ </i> ‐Symmetric Biaryls
  作者：Gavin Coombs、Marcus H. Sak、Scott J. Miller

  DOI：10.1002/anie.201913563

  日期：2020.2.10

  We have demonstrated that small, modular, tetrameric peptides featuring the Lewis-basic residue β-dimethylaminoalanine (Dmaa) are capable of atroposelectively coupling naphthols and ester-bearing quinones to yield non-C2 -symmetric BINOL-type scaffolds with good yields and enantioselectivity. The study culminates in the asymmetric synthesis of backbone-substituted scaffolds similar to 3,3'-disubstituted

  我们已经证明具有路易斯基本残基β-二甲基氨基丙氨酸（Dmaa）的小，模块化，四聚体肽能够对萘酚和带有酯的醌进行熵选择性偶联，以产生具有良好收率和对映选择性的非C2对称​​BINOL型支架。该研究最终以不对称合成类似于3,3'-双取代BINOL的骨架取代支架（如（R）-TRIP），重结晶后具有良好的（94：6 er）至优异的（> 99.9：0.1 er）对映选择性，以及修饰最小的非甾体类抗炎药（NSAID）萘普生的非对映选择性净芳基化。
• Catalytic Enantioselective Synthesis of Axially Chiral Diarylmethylidene Indanones
  作者：Prashant Kumar、Rajendra P. Shirke、Sonu Yadav、S. S. V. Ramasastry

  DOI：10.1021/acs.orglett.1c01671

  日期：2021.6.18

  triflates to access axially chiral (Z)-diarylmethylidene indanones (DAIs). The chemical, physical, and biological properties of DAIs are unknown, despite their being structurally similar to arylidene indanones, primarily due to the lack of racemic or chiral methods. Through this work, we demonstrate a general and efficient protocol for the racemic as well as the atropselective synthesis of (Z)-DAIs. An unusual

  我们描述了 β-酮烯醇三氟甲磺酸酯的第一个 atropselective Suzuki-Miyaura 交叉偶联，以获取轴向手性 ( Z )-二芳基亚甲基茚满酮 (DAI)。尽管 DAI 在结构上与亚芳基茚满酮相似，但其化学、物理和生物学特性尚不清楚，这主要是由于缺乏外消旋或手性方法。通过这项工作，我们展示了 ( Z )-DAI的外消旋和 atropselective 合成的通用和有效的协议。一个不寻常的分子内 Morita-Baylis-Hillman 反应被用于 β-酮烯醇三氟甲磺酸酯的 Z 选择性合成。
• An enantioselective oxidative coupling reaction of 2-naphthol derivatives catalyzed by chiral diphosphine oxide–iron(<scp>ii</scp>) complexes
  作者：Takahiro Horibe、Keita Nakagawa、Takashi Hazeyama、Kazuki Takeda、Kazuaki Ishihara

  DOI：10.1039/c9cc07834g

  日期：——

  An enantioselective oxidative coupling of 2-naphthol derivatives is developed with the use of chiral Fe(II)–diphosphine oxide complexes. Optically active 1,1-bi-2-naphthol derivatives can be synthesized in high yields when a 2 : 1 complex of (S)-xylyl-iPrO-BIPHEP-oxide and Fe(OTf)2 is used in the presence of t-butyl hydroperoxide as an oxidant. The non-linear effect, X-ray crystal structure and ESI-MS

  通过使用手性Fe（II）-二膦氧化物络合物，开发了2-萘酚衍生物的对映选择性氧化偶联。当在存在t的情况下使用（S）-二甲苯基-i PrO- BIPHEP-氧化物和Fe（OTf）2的2：1配合物时，可以高收率合成旋光的1,1-bi-2-萘酚衍生物丁基过氧化氢作为氧化剂。非线性效应，X射线晶体结构和ESI-MS表明（S）-二甲苯基-i PrO- BIPHEP-氧化物和Fe（OTf）2的2：1络合物是Fe（III）/ Fe（IV）氧化还原循环。
• The structure, modelling and dynamics of 2,7-diisopropoxy-1,8-diarylnaphthalenes
  作者：Carl Thirsk、Geoffrey E. Hawkes、Romano T. Kroemer、Klaus R. Liedl、Thomas Loerting、Rima Nasser、Robin G. Pritchard、Melanie Steele、John E. Warren、Andrew Whiting*

  DOI：10.1039/b201235a

  日期：2002.8.27

  2,7-Diisopropoxy-1,8-dibromonaphthalene 5 was prepared in two steps from 2,7-dihydroxynaphthalene and was coupled under Suzuki cross-coupling conditions with boronic acids 9 and 10 to provide the corresponding 1,8-diarylnaphthalene systems 12a and 13a respectively. In contrast, attempted coupling of dibromide 5 with o-tolylboronic acid 11 proved unrewarding. Single crystal X-ray structure determination of compounds 12a and 13a showed that both structures possessed a high degree of structural deformation due to high internal steric repulsions between the 1,8-diaryl rings and their substituents. Dynamic 1H NMR experiments showed that these two systems possessed very slow phenyl–naphthalene bond rotation (ca. 2 s−1), corresponding to rotation barriers (ΔG*) of 16–18 kcal mol−1. Molecular modelling predicts that such systems have approximately similar rotation barriers and that in order to completely prevent phenyl–naphthalene bond rotation, an ortho-phenyl substituent is required, with a barrier to rotation of ca. 40 kcal mol−1.

  2,7-二异丙氧基-1,8-二溴萘5是由2,7-二羟基萘分两步制备的，并在Suzuki交叉偶联条件下与硼酸9和10偶联，得到相应的1,8-二芳基萘体系12a和分别如图13a所示。相反，尝试将二溴化物 5 与邻甲苯基硼酸 11 偶联被证明是没有回报的。化合物12a和13a的单晶X射线结构测定表明，由于1,8-二芳基环与其取代基之间的高内部空间排斥，两种结构都具有高度的结构变形。 动态 1H NMR 实验表明，这两个系统具有非常慢的苯基-萘键旋转（约 2 s−1），对应于 16-18 kcal mol−1 的旋转势垒（ΔG*）。分子模型预测，此类系统具有大致相似的旋转势垒，并且为了完全防止苯基-萘键旋转，需要邻苯基取代基，其旋转势垒约为。 40 kcal mol−1。
• Phosphine-Catalyzed Asymmetric (3+2) Annulations of δ-Acetoxy Allenoates with 2-Naphthols
  作者：Dong Wang、Xiaofeng Tong

  DOI：10.1021/acs.orglett.7b03250

  日期：2017.12.1

  Phosphine-catalyzed (3+2) annulations of δ-acetoxy allenoates with 2-naphthols are reported, wherein the δC of allentoate reacts with the αC of 2-naphthol to form the C–C bond while a C–O bond is formed between the γC of allenoate and the hydroxyl group of 2-naphthol. When (R)-SITCP is used as the catalyst, 1,2-dihydronaphtho[2,1-b]furans are obtained in moderate to good yields and with high enantioselectivity. This

  据报道膦被δ-乙酰氧基烯酸酯与（2-萘酚）催化的环化反应（3 + 2），其中烯丙酸酯的δC与2-萘酚的αC反应形成CC键，而在两者之间形成一个C键。烯丙酸酯的γC和2-萘酚的羟基。当使用（R）-SITCP作为催化剂时，以中等至良好的产率和高的对映选择性获得了1,2-二氢萘并[2,1- b ]呋喃。该方法可用于通过中心至轴向手性转化策略构建对映体富集的对映异构呋喃。