B-萘基丙酸酯 | 13080-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: B-萘基丙酸酯
• 英文名称: 2-naphthyl propionate
• 英文别名: β-Naphthylpropionat；naphthalen-2-yl propanoate
• CAS: 13080-43-8
• 化学式: C₁₃H₁₂O₂
• mdl: MFCD00051170
• 分子量: 200.237
• InChiKey: KVMXEPJRCAPKJL-UHFFFAOYSA-N

物化性质

• 熔点：
  48-51 °C
• 沸点：
  324.0±11.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2915509000

反应信息

• 作为反应物：
  描述：

  B-萘基丙酸酯 在 Rsp₃₆₉₀ from Rhodobacter sphaeroides 作用下， 以 二甲基亚砜 为溶剂， 生成 2-萘酚
  参考文献：
  名称：

  Structural Characterization and Function Determination of a Nonspecific Carboxylate Esterase from the Amidohydrolase Superfamily with a Promiscuous Ability To Hydrolyze Methylphosphonate Esters

  摘要：

  The uncharacterized protein Rsp3690 from Rhodobacter sphaeroides is a member of the amidohydrolase superfamily of enzymes. In this investigation the gene for Rsp3690 was expressed in Escherichia coli and purified to homogeneity, and the three-dimensional structure was determined to a resolution of 1.8 angstrom. The protein folds as a distorted (beta/alpha)(8)-barrel, and the subunits associate as a homotetramer. The active site is localized to the C-terminal end of the beta-barrel and is highlighted by the formation of a binuclear metal center with two manganese ions that are bridged by Glu-175 and hydroxide. The remaining ligands to the metal center include His-32, His-34, His-207, His-236, and Asp-302. Rsp3690 was shown to catalyze the hydrolysis of a wide variety of carboxylate esters, in addition to organophosphate and organophosphonate esters. The best carboxylate ester substrates identified for Rsp3690 included 2-naphthyl acetate (k(cat)/K-m = 1.0 x 10(5) M-1 s(-1)), 2-naphthyl propionate (k(cat)/K-m = 1.5 x 10(5) M-1 s(-1)), 1-naphthyl acetate (k(cat)/K-m = 7.5 x 10(3) M-1 s(-1)), 4-methylumbelliferyl acetate (k(cat)/K-m = 2.7 x 10(3) M-1 s(-1)), 4-nitrophenyl acetate (k(cat)/K-m = 2.3 x 10(5) M-1 s(-1)), and 4-nitrophenyl butyrate (k(cat)/K-m = 8.8 x 10(5) M-1 s(-1)). The best organophosphonate ester substrates included ethyl 4-nitrophenyl methylphosphonate (k(cat)/K-m = 3.8 x 10(5) M-1 s(-1)) and isobutyl 4-nitrophenyl methylphosphonate (k(cat)/K-m = 1.1 x 10(4) M-1 s(-1)). The (S-p)-enantiomer of isobutyl 4-nitrophenyl methylphosphonate was hydrolyzed 10 times faster than the less toxic (R-p)-enantiomer. The high inherent catalytic activity of Rsp3690 for the hydrolysis of the toxic enantiomer of methylphosphonate esters make this enzyme an attractive target for directed evolution investigations.

  DOI：

  10.1021/bi5004266
• 作为产物：
  描述：

  三甲基(2-萘基)硅烷 、 异丁酸 在 palladium diacetate 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 溶剂黄146 为溶剂， 反应 17.0h， 以73%的产率得到B-萘基丙酸酯
  参考文献：
  名称：

  Palladium-Catalyzed Desilylative Acyloxylation of Silicon–Carbon Bonds on (Trimethylsilyl)arenes: Synthesis of Phenol Derivatives from Trimethylsilylarenes

  摘要：

  A strategy for desilylative acetoxylation of (trimethylsilyl)-arenes has been developed in which (trimethylsilyl)arenes are converted into acetoxyarenes. The direct acetoxylation is performed in the presence of 5 mol % of Pd(OAc)(2) and PhI(OCOCF3)(2) (1.5 equiv) in AcOH at 80 degrees C for 17 h. The acetoxyarenes are obtained in good to high yields (67-98%). The synthetic utility is demonstrated with a one-pot transformation of (trimethylsilyearenes to phenols by successive acetoxylation and hydrolysis. Furthermore, desilylative acyloxylation of 2-(trimethylsilyl)-naphthalene using several carboxylic acids has been conducted.

  DOI：

  10.1021/acs.orglett.5b02336

文献信息

• Electrostatic catalysis by ionic aggregates: scope and limitations of Mg(ClO4)2 as acylation catalyst
  作者：Asit K Chakraborti、Lalima Sharma、Rajesh Gulhane、Shivani

  DOI：10.1016/j.tet.2003.08.007

  日期：2003.9

  Alkali and alkaline earth metal perchlorates exhibit electrostatic catalysis in the activation of anhydrides for the acylation reaction. Perchlorates with higher values of the charge-size function of the metal ion exhibit better catalytic activity following the order Mg(ClO4)2>Ba(ClO4)2>LiClO4. Acylation of structurally diverse phenols, thiols, alcohols, and amines have been carried out with stoichiometric

  碱和碱土金属高氯酸盐在酸酐活化过程中表现出静电催化作用，可进行酰化反应。金属离子的电荷大小函数的值较高的高氯酸盐表现出更好的催化活性，遵循Mg（ClO 4）2 > Ba（ClO 4）2 > LiClO 4的顺序。在室温下，在无溶剂条件下，在催化量的Mg（ClO 4）2存在下，用化学计量的酸酐对结构多样的酚，硫醇，醇和胺进行酰化反应。受阻和电子不足的酚可被有效地酰化。与空间受阻的酸酐（如异丁酸，新戊酸和苯甲酸酐）的酰化反应可与苯酚和醇类以极高的收率进行。酸敏感的醇以极好的收率被酰化，而没有任何竞争性副反应。
• Magnesium Bistrifluoromethanesulfonimide as a New and Efficient Acylation Catalyst
  作者：Asit K. Chakraborti、Shivani

  DOI：10.1021/jo0605142

  日期：2006.7.1

  room temperature and in short times. Electron-deficient and sterically hindered phenols provided excellent yields. The catalyst was found to be general for acylation with other anhydrides, such as propionic, isobutyric, pivalic, chloroacetic, and benzoic anhydrides. The rate of acylation was influenced by the electronic and steric factors associated with the anhydride. The reaction with less electrophilic

  双三氟甲烷磺酰亚胺镁在无溶剂条件下于室温和短时间内催化酚，醇和硫醇的乙酰化。电子不足和空间受阻的苯酚可提供出色的收率。已发现该催化剂通常可与其他酸酐，如丙酸酐，异丁酸，新戊酸，氯乙酸酐和苯甲酸酐进行酰化反应。酰化的速率受与酸酐相关的电子和空间因素的影响。用较少的亲电子酸酐（例如氯乙酸酐和苯甲酸酐）进行反应需要较高的温度（约80°C）。化学选择性的乙酰化，新戊酸化和苯甲酰化是用酸敏感的醇进行的，没有任何竞争性的脱水/重排。
• Indium(III) chloride as a new, highly efficient, and versatile catalyst for acylation of phenols, thiols, alcohols, and amines
  作者：Asit K. Chakraborti、Rajesh Gulhane

  DOI：10.1016/s0040-4039(03)01641-1

  日期：2003.8

  Indium(III) chloride efficiently catalyses the acylation of structurally diverse phenols, alcohols, thiols, and amines under solvent free conditions. Acid sensitive alcohols are smoothly acylated without competitive side reactions. Acylation of 2-hydroxynaphthalene is carried out with carboxylic acids adopting the mixed anhydride protocol using trifluoroacetic anhydride.

  氯化铟（III）在无溶剂条件下有效催化结构多样的酚，醇，硫醇和胺的酰化。对酸敏感的醇被平滑酰化而没有竞争性副反应。通过使用三氟乙酸酐的混合酸酐方案，将羧酸与2-羟基萘酰化。
• Na2CO3-Catalyzed O-Acylation of Phenols for the Synthesis of Aryl Carboxylates with Use of Alkenyl Carboxylates
  作者：Xiao-Yu Zhou、Xia Chen

  DOI：10.1055/s-0037-1610265

  日期：2018.10

  phenol and its derivatives has been developed. The procedure provides an efficient catalysis system for the preparation of aryl carboxylates with alkenyl carboxylates as acyl reagents. The reaction proceeded smoothly by using ­Na2CO3 as the catalyst in MeCN to produce the corresponding aryl carboxylates in good to excellent yields.

  已开发出无机碱催化苯酚及其衍生物的 O-酰化。该方法为以烯基羧酸盐作为酰基试剂制备芳基羧酸盐提供了有效的催化体系。在 MeCN 中使用 Na2CO3 作为催化剂, 反应顺利进行, 以良好到极好的收率生产相应的芳基羧酸酯。
• METHOD FOR PRODUCING CARBOXYLIC ACID AMIDE
  申请人：Tomokawa Junichi

  公开号：US20130123505A1

  公开（公告）日：2013-05-16

  A carboxamide can be produced in a high yield by a method for producing a carboxamide, for example, represented by formula (4): (wherein R 1 and R 3 are as defined below), the method comprising a step of allowing a carboxylic acid ester represented by formula (1): (wherein R 1 represents an optionally substituented C 1 -C 20 hydrocarbon group or an optionally substituented C 3 -C 20 heterocyclic group, and R 2 represents an optionally substituented C 1 -C 20 hydrocarbon group), an amine represented by formula (2): R 3 —NH 2 (2) (wherein R 3 represents a hydrogen atom or an optionally substituented C 1 -C 20 hydrocarbon group), and a formamide compound represented by formula (3): (wherein R 3 is as defined above) to react in the presence of a metal alkoxide.

  通过一种生产羧酰胺的方法可以高产率生产羧酰胺，例如，如公式（4）所示的方法：（其中R1和R3如下定义），该方法包括允许由公式（1）表示的羧酸酯（其中R1表示可选取代的C1-C20烃基或可选取代的C3-C20杂环基，R2表示可选取代的C1-C20烃基），由公式（2）表示的胺：R3—NH2（2）（其中R3表示氢原子或可选取代的C1-C20烃基），以及由公式（3）表示的甲酰胺化合物（其中R3如上所定义）在金属烷氧化物存在下反应的步骤。

表征谱图