(R)-1,2-二乙酰氧基丁烷 | 130384-43-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (R)-1,2-二乙酰氧基丁烷
• 英文名称: (R)-1,2-Diacetoxybutane
• 英文别名: [(2R)-2-acetyloxybutyl] acetate
• CAS: 130384-43-9
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: KPTMSNPLDZKSST-MRVPVSSYSA-N

物化性质

• 沸点：
  210.1±13.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-1,2-二乙酰氧基丁烷 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (R)-1,2-丁二醇
  参考文献：
  名称：

  Lipase-catalyzed enantiomer selective hydrolysis of 1,2-diol diacetates

  摘要：

  Enantiomer selective hydrolysis of racemic 1,2-diol diacetates (rac-2a-h) was investigated by using the inexpensive commercial porcine pancreatic lipase. The hydrolysis proceeds with variable regioselectivity but with moderate to good enantioselectively yielding a mixture of isomeric monoacetates (3a-h and 4a-h) and unchanged diacetate enantiomers (2a-h). Evidence was found that both monoacetates (3a-h and 4a-h) are formed with the same sense of enantiomer selectivity.

  DOI：

  10.1016/s0957-4166(00)80071-3
• 作为产物：
  描述：

  1,2-butanediol diacetate 生成 (R)-1,2-二乙酰氧基丁烷
  参考文献：
  名称：

  Lipase-catalyzed enantiomer selective hydrolysis of 1,2-diol diacetates

  摘要：

  Enantiomer selective hydrolysis of racemic 1,2-diol diacetates (rac-2a-h) was investigated by using the inexpensive commercial porcine pancreatic lipase. The hydrolysis proceeds with variable regioselectivity but with moderate to good enantioselectively yielding a mixture of isomeric monoacetates (3a-h and 4a-h) and unchanged diacetate enantiomers (2a-h). Evidence was found that both monoacetates (3a-h and 4a-h) are formed with the same sense of enantiomer selectivity.

  DOI：

  10.1016/s0957-4166(00)80071-3

文献信息

• Enantioselective Resolution Copolymerization of <i>Racemic</i> Epoxides and Anhydrides: Efficient Approach for Stereoregular Polyesters and Chiral Epoxides
  作者：Jie Li、Bai-Hao Ren、Zhao-Qian Wan、Shi-Yu Chen、Ye Liu、Wei-Min Ren、Xiao-Bing Lu

  DOI：10.1021/jacs.9b02722

  日期：2019.6.5

  strategy for preparing isotactic polyesters and chiral epoxides via enantioselective resolution copolymerization of racemic terminal epoxides with anhydrides, mediated by enantiopure bimetallic complexes in conjunction with a nucleophilic cocatalyst. The chirality of both the axial linker and the diamine backbones of the ligand are responsible for the chiral induction of this kinetic resolution copolymerization

  在此，我们报告了一种通过外消旋末端环氧化物与酸酐的对映选择性拆分共聚制备全同立构聚酯和手性环氧化物的有效策略，由对映纯双金属配合物与亲核助催化剂共同介导。轴向接头和配体的二胺主链的手性是造成该动力学拆分共聚过程的手性诱导的原因。该催化剂体系表现出非凡的对映选择性水平，对于各种外消旋环氧化物的动力学分辨率超过 300，提供具有完全交替结构和低多分散指数的高度全同立构共聚物（选择性因子超过 300）。
• Ruthenium complexes of phosphine-aminophosphine ligands
  申请人：Boaz Neil Warren

  公开号：US06939981B1

  公开（公告）日：2005-09-06

  Disclosed are ruthenium complexes of phosphine-aminophosphine ligands that may be used to catalyze large number of reactions of a wide variety of substrates such as asymmetric hydrogenations, asymmetric reductions, asymmetric hydroborations, asymmetric olefin isomerizations, asymmetric hydrosilations, asymmetric allylations, and asymmetric organometallic additions. Also disclosed is a process for the preparation of the ruthenium complexes and processes for the enantioselective asymmetric hydrogenations of 1,3-dicarbonyl, α-hydroxycarbonyl, and β-hydroxycarbonyl compounds to produce the corresponding hydroxycarbonyl, 1,2-diol, and 1,3-diol compounds, respectively, using the ruthenium complexes to catalyze the hydrogenation.

  揭示了磷胺磷配体的钌配合物，可用于催化各种底物的大量反应，如不对称氢化、不对称还原、不对称氢硼化、不对称烯烃异构化、不对称硅氢化、不对称烯丙基化和不对称有机金属加成等。还揭示了一种制备钌配合物的方法，以及用于催化1,3-二羰基、α-羟基羰基和β-羟基羰基化合物的对映选择性不对称氢化的方法，分别产生相应的羟基羰基、1,2-二醇和1,3-二醇化合物，使用钌配合物催化氢化。
• Homochiral Metallacycle Used as a Stationary Phase for Capillary Gas Chromatographic Separation of Chiral and Achiral Compounds
  作者：Bin Huang、Kuan Li、Qi-Yu Ma、Tuan-Xiu Xiang、Rui-Xue Liang、Ya-Nan Gong、Bang-Jin Wang、Jun-Hui Zhang、Sheng-Ming Xie、Li-Ming Yuan

  DOI：10.1021/acs.analchem.3c02438

  日期：2023.9.5

  many fields. However, to the best of our knowledge, no research on the use of metallacycles as stationary phases for gas chromatographic (GC) separations has been published yet. In this work, we report for the first time the use of a homochiral metallacycle, [ZnCl2L]2, as a stationary phase for GC separations. [ZnCl2L]2 was synthesized by reaction of (S)-(1-isonicotinoylpyrrolidin-2-yl)methyl-isonicotinate

  金属环是一类新型超分子材料，具有圆形结构、内腔和丰富的主客体化学性质，在许多领域表现出良好的应用前景。然而，据我们所知，尚未发表关于使用金属环作为气相色谱（GC）分离固定相的研究。在这项工作中，我们首次报道了使用纯手性金属环[ZnCl 2 L] 2作为气相色谱分离的固定相。[ZnCl 2 L] 2通过( S )-(1-异烟酰吡咯烷-2-基)甲基异烟酸酯(L)与ZnCl 2 的配位驱动自组装反应合成。[ZnCl 2 L] 2涂层柱不仅对有机异构体而且对外消旋化合物都显示出优异的分离性能。16种外消旋体（包括醇、酯、氨基酸衍生物、醚、有机酸和环氧化物）和21种异构体化合物（包括位置异构体、结构异构体和顺/反异构体）在[ZnCl 2 L] 2涂层上得到很好的分离柱子。令人印象深刻的是，一些外消旋体以高分辨率 ( Rs ) 得到分离，包括 1,2-丁二醇二乙酸酯 ( Rs = 25.86)、3-羟基丁酸乙酯
• Kinetic resolution of aliphatic 1,2-diols by a lipase-catalyzed sequential acetylation
  作者：Fritz Theil、Judith Weidner、Sibylle Ballschuh、Annamarie Kunath、Hans Schick

  DOI：10.1016/s0040-4039(00)60573-7

  日期：1993.1

  The kinetic resolution of 13 racemic aliphatic 1,2-diols (rac-1a-m) by means of a lipase-catalyzed sequential acetylation was investigated. The enantioselectivity of the 3-aryloxy-propane-1,2-diols rac-1a-k depends on the substitution pattern at the aryl ring.
• Kinetic resolution of acyclic 1,2-diols using a sequential lipase-catalyzed transesterification in organic solvents
  作者：Fritz Theil、Judith Weidner、Sibylle Ballschuh、Annamarie Kunath、Hans Schick

  DOI：10.1021/jo00081a018

  日期：1994.1

  A method for the kinetic resolution of 3-(aryloxy)-1,2-propanediols rac-1a-n without additional protection-deprotection steps using a lipase-catalyzed sequential transesterification with lipase amnno PS has been developed. In the first step of this one-pot procedure the racemic 1,2-diols are acylated regioselectively at the primary hydroxy group without enantioselection. The subsequent acylation at the secondary hydroxy group of the formed primary monoacetate is responsible for high enantioselection. The enantioselectivity of this transformation depends significantly on the substitution pattern of the aryl ring and the organic solvent used. 3-(Aryloxy)-1,2-propanediols with substituents in the para-position show a much higher enantioselectivity than the corresponding derivatives with ortho-substituents. Among other substrates, the pharmaceuticals Mephenesin, Guaifenesin, and Chlorphenesin have been resolved. The replacement of the aryloxy by alkyl substituent causes a dramatic decrease of enantioselectivity.