4-hydroxybutyl 2-benzoate | 80403-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-hydroxybutyl 2-benzoate
• 英文别名: 4-hydroxybut-2-yl benzoate；4-Hydroxybutan-2-yl benzoate
• CAS: 80403-62-9
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: FWFFWFOJXLWTKP-UHFFFAOYSA-N

物化性质

• 沸点：
  318.6±25.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-丁二醇 、 苯甲酰氯 在 吡啶 、 resin-(C₁₀H₁₂)0.45(C₁₀H₁₀)0.40(C₁₂H₁₇SiCl)015 、 氢氟酸 作用下， 生成 4-hydroxybutyl 2-benzoate
  参考文献：
  名称：

  Functional Polymers from (Vinyl)polystyrene. Recyclable Polymer-Supported Organosilicon Protecting Groups for Solid-Phase Synthesis

  摘要：

  Dicobalt octacarbonyl catalyzed the hydrosilylation of residual vinyl groups on insoluble porous beads of divinylbenzene-rich copolymer, exclusively with beta orientation, by either dialkylhalosilanes or alkyldihalosilanes. The resulting silyl halide functionalities, now bound to a cross-linked polystyrene matrix through stable dimethylene spacers, could then be used to protect and immobilize hydroxyl-containing free molecules for their further modification in the course of solid-phase synthesis. The reaction proved selective for primary hydroxyls in the presence of secondary, and secondary over tertiary. Together with product free alcohols, later cleavage of these silyl ethers with aqueous acid or base also released the corresponding silanol groups, while HF, under particularly mild and selective conditions, left silyl fluorides that themselves could then be very conveniently regenerated by BCl3/CH2Cl2 back to the polymer-supported silyl chlorides. For a variety of possible applications, these solid-phase protecting groups offer control, yield, recovery, and reusability, as well as other possible advantages involving site-site isolation of functional groups within the cross-linked polystyrene matrix.

  DOI：

  10.1021/jo960603m

文献信息

• Dialkyl acylphosphonates: a new acylating agent of alcohols
  作者：Mitsuo Sekine、Akiko Kume、Tsujiaki Hata

  DOI：10.1016/s0040-4039(01)81975-4

  日期：1981.1

  Diethyl benzoylphosphonate (1) underwent facile benzoylation of alcohols in the presence of DBU. Reactions of diols containing primary and secondary hydroxyl groups with 1 gave predominantly monobenzoates in which primary hydroxyl groups were highly selectively benzoylated. Related acylations were also described.

  在DBU存在下，苯甲酸二乙酯二乙酯（1）进行了醇的轻松苯甲酰化。含有伯羟基和仲羟基的二醇与1的反应主要产生一苯甲酸酯，其中伯羟基被高度选择性地苯甲酰化。还描述了相关的酰化作用。
• Benzoxaborole Catalyst for Site-Selective Modification of Polyols
  作者：Shuhei Kusano、Shoto Miyamoto、Aki Matsuoka、Yuji Yamada、Ryuta Ishikawa、Osamu Hayashida

  DOI：10.1002/ejoc.201901749

  日期：2020.3.22

  Novel benzoxaborole derivatives were designed as efficient catalysts for the highly site‐selective and protecting‐group‐free modification of polyols, such as carbohydrate. Additionally, the benzoxaborole catalyst could tolerate diverse modifications of polyols, including acylation, sulfonylation, alkylation, and glycosylation.

  新型苯并氧杂硼杂环戊烷衍生物被设计为多元醇（例如碳水化合物）的高度位点选择性和无保护基团修饰的有效催化剂。另外，苯并氧杂硼烷催化剂可耐受多元醇的多种改性，包括酰化，磺酰化，烷基化和糖基化。
• Chemo- and Stereoselective Monobenzoylation of 1,2-Diols Catalyzed by Organotin Compounds
  作者：Fumiaki Iwasaki、Toshihide Maki、Osamu Onomura、Waka Nakashima、Yoshihiro Matsumura

  DOI：10.1021/jo991394j

  日期：2000.2.1

  acyclic diols, in particular 1,2-diols, were selectively monobenzoylated in good yields by the reaction with benzoyl chloride in the presence of a catalytic amount of dimethyltin dichloride and inorganic bases such as potassium carbonate. Furthermore, the method was successfully applied to a kinetic resolution of racemic 1-phenyl-1,2-ethanediol using a chiral organotin catalyst. The ee was dependent

  已经开发了一种新的简便的二醇单酰化方法。通过在催化量的二氯化二甲基锡和无机碱例如碳酸钾的存在下，通过与苯甲酰氯反应，以高收率选择性地将多种环状和无环二醇，特别是1,2-二醇选择性地单苯甲酰化。此外，该方法已成功地用于使用手性有机锡催化剂的外消旋1-苯基-1,2-乙二醇的动力学拆分。ee取决于碱的种类，作为添加剂的水和反应温度。
• Selective mono-acylation of 1,2- and 1,3-diols using (α,α-difluoroalkyl)amines
  作者：Natsumi Wakita、Shoji Hara

  DOI：10.1016/j.tet.2010.08.029

  日期：2010.10

  3-diols, selective mono-benzoylation occurs to afford mono-esters of the diols in good yield. The reaction is completed under mild conditions in a short reaction time. Further, prim-, sec-, and tert-diols and catechol can be converted to the corresponding mono-benzoates. DFBA is used for the protection of the hydroxy group in sugars. The selective mono-nicotinylation, formylation and pivaloylation of diols

  在N，N-二乙基-α，α-二氟苄胺（DFBA）与1,2-或1,3-二醇的反应中，发生选择性的单苯甲酰化以良好的产率提供二醇的单酯。反应在温和的条件下在短时间内完成。此外，整洁- ，仲- ，和叔-diols和儿茶酚可以转化为相应的单苯甲酸酯。DFBA用于保护糖中的羟基。还通过使用相应的二氟烷基胺来进行二醇的选择性单-烟酰胺基化，甲酰化和聚乙烯醇缩合。
• Palladium(II)-catalysed oxidative ring cleavage of cyclic acetals with t-butyl hydroperoxide: preparation of monoesters of diols
  作者：Takahiro Hosokawa、Yasushi Imada、Shun-Ichi Murahashi

  DOI：10.1039/c39830001245

  日期：——

  Reaction of five- and six-membered cyclic acetals with ButOOH in the presence of palladium(II) catalyst gives monoesters of diols in good yields.

  的五元环和反应六元与卜环状缩醛吨OOH在钯的存在下（II）的催化剂，得到高收率的二醇的单酯。