(-)-(R)-1,3-diacetoxybutane | 128443-70-9

• 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
• 英文名称: (-)-(R)-1,3-diacetoxybutane
• 英文别名: (R)-1,3-di-O-acetyl-1,3-butanediol；(3R)-1.3-Diacetoxy-butan；1,3-Butanediol diacetate, (R)-；[(3R)-3-acetyloxybutyl] acetate
• CAS: 128443-70-9
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: MPAGVACEWQNVQO-ZCFIWIBFSA-N

物化性质

• 沸点：
  228.8±0.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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

• 作为产物：
  描述：

  1,3-丁二醇 、 乙酸酐 在 4-二甲氨基吡啶 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以81.8%的产率得到
  参考文献：
  名称：

  Ruthenium complexes of phosphine-aminophosphine ligands

  摘要：

  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。

  公开号：

  US06939981B1

文献信息

• 1,4 Asymmetric induction in the carbonyl reduction of a γ-ketosulfoxide
  作者：Guy Solladie、Françoise Colobert、Frédéric Somny

  DOI：10.1016/s0040-4039(98)02572-6

  日期：1999.2

  a chiral sulfoxide induced high stereoselectivity in the DIBAL-H reduction of a methyl ketone located in the γ position as a result of a 1,4-asymmetric induction. Addition of a lanthanide triflate or cerium chloride completely reversed the stereoselectivity.

  1，4-不对称诱导的结果是，手性亚砜在位于γ位的甲基酮的DIBAL-H还原中诱导了高立体选择性。加入三氟化镧或氯化铈可完全逆转立体选择性。
• 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
• 10.1021/acs.joc.4c00776
  作者：Deng, Meng、Yang, Jiaqi、Kong, Zhiyi、Li, Yaning、Wang, Quanpeng、Liu, Huan、Deng, Shu-Zhen、Li, Nan

  DOI：10.1021/acs.joc.4c00776

  日期：——

  the production of optically active γ-functionalized alcohols from relevant alkenes has been developed by using a robust Mn(III)/air/(Me2SiH)2O catalytic system combined with lipase-catalyzed kinetic resolution. This approach demonstrates exceptional tolerance toward proximal functional groups present on alkenes, enabling the achievement of high yields and exclusive enantioselectivity. Under this sequential

  通过使用稳健的 Mn(III)/空气/(Me 2 SiH) 2 O 催化系统与脂肪酶催化动力学拆分相结合，开发了一种简单实用的催化工艺，用于从相关烯烃生产光学活性 γ-官能化醇。该方法表现出对烯烃上存在的近端官能团的优异耐受性，从而实现高产率和独特的对映选择性。在这种顺序催化系统下，手性烯烃前体也可以转化为γ-官能化醇和相关的乙酸酯作为可分离的单一对映体。
• Lipase mediated resolution of 1,3-butanediol derivatives: chiral building blocks for pheromone enantiosynthesis. Part 3
  作者：Isidoro Izquierdo、Marı́a T. Plaza、Miguel Rodrı́guez、Juan A. Tamayo、Alicia Martos

  DOI：10.1016/s0957-4166(01)00038-6

  日期：2001.2

  (R,S)-1,3-butanediol 5 was kinetically resolved by enzymatic acetylation with vinyl acetate under the presence of Chirazyme (TM) L-2, c-f, yielding (S)-1-O-acetyl-1,3-hydroxybutane 6 and (R)-1,3-di-O-acetyl-1,3-butanediol 7 with enantiomeric excesses of 91%, (E=67.3). Compounds 6 and 7 were easily transformed into the corresponding (S)-3-O-(2-methoxyethoxymethyl)-3-hydroxybutanal 10 and (R)-3-benzyloxybutanal 19, through a protection-deprotection and functional group interchange methodology. Subsequent reaction of 10 and 19 with 3-(methoxycarbonlypropionyl-methylene)triphenylphosphorane afforded methyl (E,S)-8-O-(2-methoxyethoxymethyl)-4-oxo-5-nonenoate 12 and (E,R)-8-benzyl-oxy-4-oxo-5-nonenoate 20. The alkenes 19 and 20 were then catalytically hydrogenated to the corresponding saturated eaters 13 and 21. Treatment of 13 and 21 with 1,2-ethanedithiol/F3B . OEt2 afforded dithioketals 14 and 22, which were respectively reduced to (S)-1,8-dihydroxy-4-nonanone ethylidenedithioketal 15 and (R)-8-O-benzyl-1,8-dihydroxy-4-nonanone ethylidenedithioketal 23. Finally, deprotection of 15 by catalytic hydrogenation under acidic conditions gave the expected (5S,7S)-(-)-7-methy1-1,6-dioxaspiro[4.5]decane 1. The (5R,7R)-(+)-1 enantiomer was analogously prepared fi om 23. Both compounds were formed by this procedure with an e.e. of 91%. (C) 2001 Elsevier Science Ltd. All rights reserved.
• RUTHENIUM COMPLEXES OF PHOSPHINE-AMINOPHOSPHINE LIGANDS
  申请人：EASTMAN CHEMICAL COMPANY

  公开号：EP1758913B1

  公开（公告）日：2007-11-14