(S)-1-hydroxypropan-2-yl benzoate | 113566-73-7

• 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: (S)-1-hydroxypropan-2-yl benzoate
• 英文别名: (S)-2-O-benzoylpropane-1,2-diol；(S)-2-(benzoyloxy)-1-propanol；[(2S)-1-hydroxypropan-2-yl] benzoate
• CAS: 113566-73-7
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: LBPLLQWWWCNJBE-QMMMGPOBSA-N

物化性质

• 沸点：
  295.2±23.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (S)-1-methyl-2-oxoethyl benzoate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 (S)-1-hydroxypropan-2-yl benzoate
  参考文献：
  名称：

  Kano, Taichi; Mii, Haruka; Maruoka, Keiji, Journal of the American Chemical Society, 2009, vol. 131, p. 3450 - 3451

  摘要：

  DOI：

文献信息

• Diphenylprolinol silyl ether as a catalyst in an asymmetric, catalytic and direct α-benzoyloxylation of aldehydes
  作者：Hiroaki Gotoh、Yujiro Hayashi

  DOI：10.1039/b902287b

  日期：——

  Diphenylprolinol silyl ether was found to promote asymmetric, catalytic and direct α-benzoyloxylation of aldehydes with benzoyl peroxide to afford oxidized products in good yields with excellent enantioselectivity.

  研究发现，二苯基脯氨醇硅基醚可促进醛与过氧化苯甲酰的不对称、催化和直接δ-苯甲酰氧基化反应，从而以良好的收率和优异的对映选择性得到氧化产物。
• Lipase-catalyzed alcoholysis of diol dibenzoates: selective enzymatic access to the 2-benzoyl ester of 1,2-propanediol and preparation of the enantiomerically pure (R)-1-O-benzoyl-2-methylpropane-1,3-diol
  作者：Enzo Santaniello、Silvana Casati、Pierangela Ciuffreda、Luca Gamberoni

  DOI：10.1016/j.tetasy.2005.03.019

  日期：2005.5

  Enzymatic debenzoylation of 1,2-propanediol dibenzoate with 1-octanol has been studied in organic solvent using lipases from different sources. In general a slow, highly regioselective alcoholysis in diisopropyl ether affords exclusively a monoester benzoylated at the secondary hydroxy group although the reaction proceeds with low enantioselectivity. In the presence of Pseudomonas cepacia lipase absorbed

  已经在有机溶剂中使用不同来源的脂肪酶研究了1-2-丙二醇与1,2-丙二醇二苯甲酸酯的酶脱苯甲酰化反应。通常，尽管该反应以低对映选择性进行，但是在二异丙醚中缓慢，高度区域选择性的醇解仅提供在仲羟基上被苯甲酰化的单酯。在存在洋葱假单胞菌的脂肪酶吸附到硅藻土上，更快的反应允许（的2-苯甲酰基酯的制备- [R）-1,2-丙二醇（82％ee）和对映体纯（- [R）-1- ø -苯甲酰基-2-甲基丙烷-1,3-二醇（> 98％ee）。
• Kinetic Resolution of 1,2-Diols Using Nitrogen-Tethered Bisimidazoline-Copper(I) Catalyzed Benzoylation
  作者：Takayoshi Arai、Tomoe Mizukami、Asami Mishiro、Akira Yanagisawa

  DOI：10.3987/com-08-s(n)59

  日期：——

  Nitrogen-tethered bisimidazoline (Nb-imidazoline) ligand was utilized in the Cu(I)-catalyzed benzoylation of 1,2-diols. With the assistance of i-Pr(2)NEt, the reaction of rac-1,2-diols with o-methylbenzoyl chloride was smoothly catalyzed by Nb-imidazoline-CuCl in CH(2)Cl(2) to give the corresponding o-methylbenzoylated secondary alcohols in tip to 79% ee.
• Organocatalytic α-oxybenzoylation of aldehydes
  作者：Matti J.P. Vaismaa、Sze Chak Yau、Nicholas C.O. Tomkinson

  DOI：10.1016/j.tetlet.2009.03.082

  日期：2009.7

  A simple method for the asymmetric alpha-oxybenzoylation of aldehydes is presented. Treatment of a series of aldehydes with benzoyl peroxide in the presence of a MacMillan imidazolidinone leads directly to the alpha-oxybenzoylated product with excellent levels of asymmetric induction. (C) 2009 Elsevier Ltd. All rights reserved.
• Chemoselective benzoylations of 1,2-diols. Reactivity comparisons of reagents. Triphenylphosphine-benzoyl peroxide and triphenylphosphine-diethyl azodicarboxylate-benzoic acid
  作者：Anne M. Pautard、Slayton A. Evans

  DOI：10.1021/jo00245a031

  日期：1988.5