(S)-1-O-acetyl-1,3-butanediol | 128402-22-2

• 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: (S)-1-O-acetyl-1,3-butanediol
• 英文别名: (S)-3-hydroxybutyl acetate；(S)-acetic acid 3-hydroxy-butyl ester；[(3S)-3-hydroxybutyl] acetate
• CAS: 128402-22-2
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: KLUHZXMBIDAHSJ-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-O-acetyl-1,3-butanediol 在 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Design and Synthesis of Dual Peroxisome Proliferator-Activated Receptors γ and δ Agonists as Novel Euglycemic Agents with a Reduced Weight Gain Profile

  摘要：

  The design and synthesis of the dual peroxisome proliferator-activated receptor ( PPAR) gamma/delta agonist (R)-3-{4-[3-(4-chloro-2-phenoxyphenoxy)-butoxy]-2-ethyl-phenyl}-propionic acid (20) for the treatment of type 2 diabetes and associated dyslipidemia is described. The compound possesses a potent dual hPPAR gamma/delta agonist profile (IC50 = 19 nM/4 nM; EC50 = 102 nM/6 nM for hPPAR gamma and hPPAR delta, respectively). In preclinical models, the compound improves insulin sensitivity and reverses diabetic hyperglycemia with less weight gain at a given level of glucose control relative to rosiglitazone.

  DOI：

  10.1021/jm060617c
• 作为产物：
  描述：

  (S)-(+)-1,3-丁二醇 、 乙酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以82 %的产率得到(S)-1-O-acetyl-1,3-butanediol
  参考文献：
  名称：

  铱(III) 催化分子间 C(sp3)-H 酰胺化合成手性 1,2-二胺

  摘要：

  设计了基于樟脑磺酸的导向基团，用于 Ir 催化的 α-仲胺和 α-叔胺的 C−H 酰胺化，从而合成手性 1,2-二胺。机理研究为 α-仲胺的 C−H 酰胺化中观察到的匹配/不匹配效应提供了见解。

  DOI：

  10.1002/anie.202309263

文献信息

• [EN] PPAR MODULATORS<br/>[FR] MODULATEURS DU RECEPTEUR ACTIVE DE LA PROLIFERATION DES PEROXYSOMES (PPAR)
  申请人：LILLY CO ELI

  公开号：WO2005019151A1

  公开（公告）日：2005-03-03

  The present invention is directed to a compound of formula I, or a pharmaceutically acceptable salt, solvate, hydrate or stereoisomer thereof, which is useful in treating or preventing disorders mediated by a peroxisome proliferator activated receptor (PPAR) such as syndrome X, type II diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, arteriosclerosis, and other disorders related to syndrome X and cardiovascular diseases.

  本发明涉及一种具有式I的化合物，或其药学上可接受的盐、溶剂合物、水合物或立体异构体，该化合物在治疗或预防由过氧化物酶体增殖物激活受体（PPAR）介导的疾病中具有用途，如X综合征、2型糖尿病、高血糖、高脂血症、肥胖、凝血障碍、高血压、动脉硬化以及与X综合征和心血管疾病相关的其他疾病。
• Manganese/Enzyme Sequential Catalytic Pathway for the Production of Optically Active γ-Functionalized Alcohols
  作者：Meng Deng、Jiaqi Yang、Zhiyi Kong、Yaning Li、Quanpeng Wang、Huan Liu、Shu-Zhen Deng、Nan Li

  DOI：10.1021/acs.joc.4c00776

  日期：2024.6.21

  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.