2-hydroxy-3-phenoxypropyl benzoate | 119740-88-4

• 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: 2-hydroxy-3-phenoxypropyl benzoate
• 英文别名: Benzoic acid-2-hydroxy-3-phenoxypropylester；(2-hydroxy-3-phenoxypropyl) benzoate
• CAS: 119740-88-4
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: ZZPYJQYIRJCUOP-UHFFFAOYSA-N

物化性质

• 沸点：
  448.1±35.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 2-hydroxy-3-phenoxypropyl benzoate 以 四氢呋喃 为溶剂， 反应 162.0h， 以17%的产率得到(S)-2-acetoxy-1-benzoyloxy-3-phenoxypropane
  参考文献：
  名称：

  Lipase-catalysed resolution of 3-(aryloxy)-1,2-propanediol derivatives — Towards an improved active site model of Pseudomonas cepacia lipase (amano PS)

  摘要：

  A variety of 3-(aryloxy)-1,2-propanediol derivatives with different substituents on the aromatic ring or at the primary hydroxy group were used as substrates in a kinetic resolution by transesterification with vinyl acetate catalysed by lipase from Pseudomonas cepacia (Amano PS). Derivatives with substituents in the para-position of the aromatic ring were accepted as substrates and resolved with high enantioselectivity. The corresponding derivatives with substituents in the ortho-position were much worse substrates for lipase PS or even non-substrates if the substituent was sufficiently space-filling as found for the tert-butyl, phenyl, benzyl or benzoyl residue. Otherwise, if the primary hydroxy group was substituted by unbranched long-chain acyl residues very good substrates were resulting. In contrast, derivatives with sterically crowded residues at the primary hydroxy group such as the pivaloyl, tert-butyldimethylsilyl, methanesulfonyl, para-toluenesulfonyl or trityl groups were nonsubstrates for lipase PS.

  DOI：

  10.1016/0957-4166(95)00166-m
• 作为产物：
  描述：

  Benzoic acid 1-hydroxymethyl-2-phenoxy-ethyl ester 在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.25h， 以85.1%的产率得到2-hydroxy-3-phenoxypropyl benzoate
  参考文献：
  名称：

  一种基于磺酸催化的羟基间苯甲酰基定向迁移的方法

  摘要：

  本发明公开了一种基于磺酸催化的羟基间苯甲酰基定向迁移的方法，涉及化学合成技术领域，具体为苯甲酰基在磺酸的催化条件，经原酸酯中间体的途经高区域选择性的完成酰基的迁移，迁移的特征表现为：在空间上能形成5元原酸酯环或6元原酸酯环的两个羟基，苯甲酰基可从仲羟基或叔羟基迁移至伯羟基，从直立位仲羟基上迁移至平复位仲羟基。本发明利用磺酸促进底物中的酰基官能团发生了1,2‑或1,3‑迁移反应，整个合成反应条件温和，操作简单，原子经济。

  公开号：

  CN110724173B

文献信息

• Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase
  作者：Yuchao Lu、Chenxi Hou、Jingli Ren、Xiaoting Xin、Hengfu Xu、Yuxin Pei、Hai Dong、Zhichao Pei

  DOI：10.3390/molecules21050641

  日期：——

  A novel metal-free organobase-catalyzed regioselective benzoylation of diols and carbohydrates has been developed. Treatment of diol and carbohydrate substrates with 1.1 equiv. of 1-benzoylimidazole and 0.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in MeCN under mild conditions resulted in highly regioselective benzoylation for the primary hydroxyl group. Importantly, compared to most commonly

  已经开发出一种新型的无金属有机碱催化的二醇和碳水化合物的区域选择性苯甲酰化。用 1.1 当量处理二醇和碳水化合物底物。1-苯甲酰咪唑和 0.2 当量。1,8-二氮杂双环[5.4.0] undec-7-ene (DBU) 在温和条件下在 MeCN 中的反应导致伯羟基的高度区域选择性苯甲酰化。重要的是，与最常用的伯羟基保护基团相比，苯甲酰基保护基团提供了一种新的保护策略。
• Regioselective Sulfonylation/Acylation of Carbohydrates Catalyzed by FeCl₃ Combined with Benzoyltrifluoroacetone and Its Mechanism Study
  作者：Jian Lv、Jia-Jia Zhu、Yu Liu、Hai Dong

  DOI：10.1021/acs.joc.9b03128

  日期：2020.3.6

  A catalytic amount of FeCl3 combined with benzoyl trifluoroacetone (Hbtfa) (FeCl3/Hbtfa = 1/2) was used to catalyze sulfonylation/acylation of diols and polyols using diisopropylethylamine (DIPEA) or potassium carbonate (K2CO3) as a base. The catalytic system exhibited high catalytic activity, leading to excellent isolated yields of sulfonylation/acylation products with high regioselectivities. Mechanism

  使用二异丙基乙胺（DIPEA）或碳酸钾（K2CO3）作为碱，将催化量的FeCl3与苯甲酰基三氟丙酮（Hbtfa）（FeCl3 / Hbtfa = 1/2）结合用于催化二醇和多元醇的磺酰化/酰化。该催化体系表现出高催化活性，导致具有高区域选择性的磺酰化/酰化产物的优异分离产率。机理研究表明，FeCl3最初在碱性条件下于室温下于溶剂乙腈中以两倍的Hbtfa量形成[Fe（btfa）3]（btfa =苯甲酰基三氟丙酮酸酯）。然后，在碱的存在下，Fe（btfa）3和底物的两个羟基形成五元或六元环中间体。环状中间体和磺酰化试剂之间的随后反应导致底物的选择性磺酰化。所有关键中间体均在高分辨率质谱分析中捕获，因此首次证明了这种机理。
• An inexpensive catalyst, Fe(acac)₃, for regio/site-selective acylation of diols and carbohydrates containing a 1,2-<i>cis</i>-diol
  作者：Jian Lv、Jian-Tao Ge、Tao Luo、Hai Dong

  DOI：10.1039/c8gc00428e

  日期：——

  This work describes the [Fe(acac)3] (acac = acetylacetonate)-catalyzed, regio/site-selective acylation of 1,2- and 1,3-diols and glycosides containing a cis-vicinal diol. The iron(III) catalysts initially formed cyclic dioxolane-type intermediates with substrates between the iron(III) species and vicinal diols, and the efficient and selective acylation of one hydroxyl group was subsequently achieved

  这项工作描述了[Fe（acac）3 ]（acac =乙酰丙酮酸酯）催化的1,2-和1,3-二醇和含有顺式邻位二醇的糖苷的区域/位点选择性酰化。铁（III）催化剂最初形成环状二氧戊环型中间体，底物在铁（III）物种与邻位二醇之间，随后通过在二异丙基乙胺（DIPEA）存在下添加酰化试剂，实现一个羟基的有效和选择性酰化）在温和的条件下。该反应通常产生高选择性和高分离产率，并具有与二丁基氧化锡介导的方案相同的保护模式。
• Stannous chloride as a low toxicity and extremely cheap catalyst for regio-/site-selective acylation with unusually broad substrate scope
  作者：Jian Lv、Jian-Cheng Yu、Guang-Jing Feng、Tao Luo、Hai Dong

  DOI：10.1039/d0gc02739a

  日期：——

  containing cis-vicinal diol, the substrate scope also includes glycosides without cis-vicinal diol. For such a substrate scope, usually, only methods using stoichiometric amounts of organotin reagents can lead to the same protection pattern with high selectivities and highly isolated yields (84–97% in most cases). Therefore, SnCl2, as a low toxicity and extremely cheap reagent, should be the best catalyst

  这项工作报告了氯化亚锡（SnCl 2）催化的区域/位点选择性酰化反应，其底物范围异常广泛。除了含有顺式-邻位二醇的1,2-和1,3-二醇和糖苷外，底物范围还包括不含顺式-邻位二醇的糖苷。对于这种底物范围，通常，只有使用化学计量的有机锡试剂的方法才能以高选择性和高分离产率（大多数情况下为84–97％）产生相同的保护模式。因此，与以前报道的任何试剂相比，SnCl 2作为一种低毒且极其便宜的试剂，应该是区域/位点选择性酰化反应的最佳催化剂。
• An Efficient Method for the Chemoselective Preparation of Benzoylated 1,2-Diols from Epoxides
  作者：A. Khalafi-Nezhad、M. N. Soltani Rad、A. Khoshnood

  DOI：10.1055/s-2003-42416

  日期：——

  A very efficient and highly regioselective ring-opening reaction of epoxides with benzoic acid and its derivatives in the presence of cat. amount of tetrabutylammonium bromide (TBAB) in anhydrous acetonitrile has been developed. This effective method is useful for the preparation of selectively protected diols as precursor for many organic syntheses such as those of acyclic nucleosides and other synthetic

  在 cat 存在下，环氧化物与苯甲酸及其衍生物的一种非常有效和高度区域选择性的开环反应。已开发出溶于无水乙腈中的四丁基溴化铵 (TBAB)。这种有效的方法可用于制备选择性保护的二醇作为许多有机合成的前体，例如无环核苷和其他合成目的。该方法的优点是高效、选择性、成本低，适用于大规模合成β-苯甲酰氧基链烷醇。