4-(2-Hydroxyethyl)-1-naphthaldehyde | 591753-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(2-Hydroxyethyl)-1-naphthaldehyde
• 英文别名: 4-(2-Hydroxyethyl)naphthalene-1-carbaldehyde
• CAS: 591753-15-0
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: HVIMNVQZFZBEST-UHFFFAOYSA-N

物化性质

• 沸点：
  402.1±20.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-Hydroxyethyl)-1-naphthaldehyde 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 12.0h， 生成 2-(4-(cyano((diethoxyphosphoryl)oxy)methyl)naphthalen-1-yl)ethyl acetate
  参考文献：
  名称：

  Dearomative Allylation of Naphthyl Cyanohydrins by Palladium Catalysis: Catalyst-Enhanced Site Selectivity

  摘要：

  A dearomative allylation of naphthyl cyanohydrins with allyl borates and allyl stannanes under palladium catalysis was developed. At the initial stage of this study, the dearomative reaction (C4 substitution of the aromatics) was competing with benzyl substitution. To circumvent this issue, the use of palladium and meta-disubstituted triarylphosphine as the catalyst in a 1:1 ratio was found to enhance the site selectivity, furnishing the desired dearomatized products. Further derivatizations of products were also successful.

  DOI：

  10.1021/acs.orglett.0c00897
• 作为产物：
  描述：

  1-萘乙醇 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 1.25h， 生成 4-(2-Hydroxyethyl)-1-naphthaldehyde
  参考文献：
  名称：

  Dearomative Allylation of Naphthyl Cyanohydrins by Palladium Catalysis: Catalyst-Enhanced Site Selectivity

  摘要：

  A dearomative allylation of naphthyl cyanohydrins with allyl borates and allyl stannanes under palladium catalysis was developed. At the initial stage of this study, the dearomative reaction (C4 substitution of the aromatics) was competing with benzyl substitution. To circumvent this issue, the use of palladium and meta-disubstituted triarylphosphine as the catalyst in a 1:1 ratio was found to enhance the site selectivity, furnishing the desired dearomatized products. Further derivatizations of products were also successful.

  DOI：

  10.1021/acs.orglett.0c00897

文献信息

• Glucagon antagonists/inverse agonists
  申请人：Novo Nordisk A/S

  公开号：US06613942B1

  公开（公告）日：2003-09-02

  Non-peptide compounds comprising a central hydrazide motif and methods for the synthesis thereof are disclosed. The compounds act to antagonize the action of the glucagon peptide hormone.

  本发明公开了包含中央腙基结构的非肽化合物及其合成方法。这些化合物具有拮抗胰高血糖素肽激素作用的作用。
• [EN] GLUCAGON ANTAGONISTS/INVERSE AGONISTS<br/>[FR] ANTAGONISTES/AGONISTES INVERSES DU GLUCAGON
  申请人：NOVO NORDISK AS

  公开号：WO1999001423A1

  公开（公告）日：1999-01-14

  Non-peptide compounds comprising a central hydrazide motif and methods for the synthesis thereof. The compounds act to antagonize the action of the glucagon peptide hormone.

  非肽化合物包含一个中心肼基结构，并且其合成方法。这些化合物作用是拮抗胰高血糖素肽激素的作用。
• GLUCAGON ANTAGONISTS/INVERSE AGONISTS
  申请人：NOVO NORDISK A/S

  公开号：EP0994848A1

  公开（公告）日：2000-04-26
• US6613942B1
  申请人：——

  公开号：US6613942B1

  公开（公告）日：2003-09-02
• Dearomative Allylation of Naphthyl Cyanohydrins by Palladium Catalysis: Catalyst-Enhanced Site Selectivity
  作者：Aika Yanagimoto、Masaaki Komatsuda、Kei Muto、Junichiro Yamaguchi

  DOI：10.1021/acs.orglett.0c00897

  日期：2020.5.1

  A dearomative allylation of naphthyl cyanohydrins with allyl borates and allyl stannanes under palladium catalysis was developed. At the initial stage of this study, the dearomative reaction (C4 substitution of the aromatics) was competing with benzyl substitution. To circumvent this issue, the use of palladium and meta-disubstituted triarylphosphine as the catalyst in a 1:1 ratio was found to enhance the site selectivity, furnishing the desired dearomatized products. Further derivatizations of products were also successful.