(3-hydroxy-2-naphthalenyl)methyl benzoate | 383150-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3-hydroxy-2-naphthalenyl)methyl benzoate
• 英文别名: (3-hydroxy-[2]naphthyl)-methyl benzoate；(3-hydroxy-2-naphthyl)-methyl benzoate；(3-hydroxy-2-naphthyl)methyl benzoate；(3-Hydroxynaphthalen-2-yl)methyl benzoate
• CAS: 383150-18-3
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: NHVRRSUTBCSFRT-UHFFFAOYSA-N

物化性质

• 沸点：
  466.9±20.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (3-hydroxy-2-naphthalenyl)methyl benzoate 以 水 、 乙腈 为溶剂， 生成 3-(羟基甲基)萘-2-醇
  参考文献：
  名称：

  用3-羟基-2-萘甲醇对醇，酚和羧酸进行光不稳定的保护。

  摘要：

  用（3-羟基-2-萘基）甲基辐照“笼中”的醇，酚和羧酸可导致底物快速（k（释放）大约= 10（5）s（-1））释放，良好的量子（Phi = 0.17-0.26）和化学（> 90％）产率。光反应的初始副产物2-萘醌-3-甲基化物与水快速反应（k（H2O）= 144 +/- 11 s（-1）），生成母体3-羟基-2-萘甲醇。邻醌甲基化物中间体也可被其他亲核试剂捕获或与乙基乙烯基醚转化为光稳定的Diels-Alder加合物。

  DOI：

  10.1021/jo801302m
• 作为产物：
  描述：

  [3-(tert-butyldimethylsilyloxy)-2-naphthalenyl]methyl benzoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以87%的产率得到(3-hydroxy-2-naphthalenyl)methyl benzoate
  参考文献：
  名称：

  用3-羟基-2-萘甲醇对醇，酚和羧酸进行光不稳定的保护。

  摘要：

  用（3-羟基-2-萘基）甲基辐照“笼中”的醇，酚和羧酸可导致底物快速（k（释放）大约= 10（5）s（-1））释放，良好的量子（Phi = 0.17-0.26）和化学（> 90％）产率。光反应的初始副产物2-萘醌-3-甲基化物与水快速反应（k（H2O）= 144 +/- 11 s（-1）），生成母体3-羟基-2-萘甲醇。邻醌甲基化物中间体也可被其他亲核试剂捕获或与乙基乙烯基醚转化为光稳定的Diels-Alder加合物。

  DOI：

  10.1021/jo801302m

文献信息

• Nucleophilic Acyl Substitutions of Anhydrides with Protic Nucleophiles Catalyzed by Amphoteric, Oxomolybdenum Species
  作者：Chien-Tien Chen、Jen-Huang Kuo、Vijay D. Pawar、Yogesh S. Munot、Shieu-Shien Weng、Cheng-Hsiu Ku、Cheng-Yuan Liu

  DOI：10.1021/jo048363v

  日期：2005.2.1

  [GRAPHICS]Among six different group VIb oxometallic species examined, dioxomolybdenum dichloride and oxomolybdenum tetrachloride were the most efficient catalysts to facilitate nucleophilic acyl substitution (NAS) of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. In contrast to the well-recognized redox chemical behaviors associated with oxomolybdenum(VI) species, the catalytic NAS was unprecedented and tolerates virtually all kinds of functional groups. By using benzoic anhydride as a mediator for in situ generation of an incipient mixed anhydride -MoO2Cl2 adduct with a given functional alkanoic acid, one can achieve oleate, dipeptide, diphenylmethyl, N-Fmoc-alpha-amino, pyruvic, and tert-butylthio ester, N-tert-butylamide, and trityl methacrylate syntheses with appropriate protic nucleophiles. The amphoteric character of the Mo=O unit in oxomolybdenum chlorides was found to be responsible for the catalytic NAS profile as supported by a control NAS reaction of using an authentic adduct-MoOCl2(O-2-CBut)(2) between pivalic anhydride and MoO2Cl2 as the catalyst.
• Transesterification catalyzed by iron(III) β-diketonate species
  作者：Shiue-Shien Weng、Chih-Shueh Ke、Fong-Kuang Chen、You-Fu Lyu、Guan-Ying Lin

  DOI：10.1016/j.tet.2011.01.009

  日期：2011.3

  A practical and clean protocol for transesterification catalyzed by a 5 mol % cheap, non-toxic and moisture stable Fe(acac)(3) or other iron(III) beta-diketonate species in solvent, such as heptane under azeotropic condition is developed. A remarkable rate enhancement was observed upon the addition of 5 mol % of an inorganic base, such as Na2CO3, which suggests that faster formation of a dimeric mu-alkoxy-bridged iron (III) species under alkaline conditions facilitates catalytic turnover. This system provides smooth transesterification over a wide range of structurally diverse esters and alcohols without disturbing functional groups. In addition, the use of iron beta-diketonate complexes as catalysts is more environmentally friendly, safer, and economical than other transition-metal catalysts. Preliminary mechanistic studies indicate that the active catalyst is likely a dimeric mu-alkoxy-bridged iron(III) species, as determined by X-ray crystallography of [Fe(dbm)(2)(O-n-Bu)](2) derived from the alcoholysis of Fe(dbm)(3) under alkaline conditions. (C) 2011 Elsevier Ltd. All rights reserved.
• Photolabile Protection of Alcohols, Phenols, and Carboxylic Acids with 3-Hydroxy-2-Naphthalenemethanol
  作者：Anton Kulikov、Selvanathan Arumugam、Vladimir V. Popik

  DOI：10.1021/jo801302m

  日期：2008.10.3

  = 0.17-0.26) and chemical (>90%) yields. The initial byproduct of the photoreaction, 2-naphthoquinone-3-methide, reacts rapidly with water (k(H2O) = 144 +/- 11 s(-1)) to produce parent 3-hydroxy-2-naphthalenemethanol. The o-quinone methide intermediate can be also trapped by other nucleophiles or converted into a photostable Diels-Alder adduct with ethyl vinyl ether.

  用（3-羟基-2-萘基）甲基辐照“笼中”的醇，酚和羧酸可导致底物快速（k（释放）大约= 10（5）s（-1））释放，良好的量子（Phi = 0.17-0.26）和化学（> 90％）产率。光反应的初始副产物2-萘醌-3-甲基化物与水快速反应（k（H2O）= 144 +/- 11 s（-1）），生成母体3-羟基-2-萘甲醇。邻醌甲基化物中间体也可被其他亲核试剂捕获或与乙基乙烯基醚转化为光稳定的Diels-Alder加合物。