(S)-5-((S)-1-hydroxyethyl)dihydrofuran-2(3H)-one | 56452-73-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-5-((S)-1-hydroxyethyl)dihydrofuran-2(3H)-one
• 英文别名: (4S,5S)-5-hydroxy-4-hexanolide；(S)-5-((S)-1-Hydroxyethyl)dihydrofuran-2(3H)-one；(5S)-5-[(1S)-1-hydroxyethyl]oxolan-2-one
• CAS: 56452-73-4
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: KBLZKAKKJPDYKJ-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• 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)-5-((S)-1-hydroxyethyl)dihydrofuran-2(3H)-one 在 diisobutylaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以75%的产率得到2,3,6-tri-deoxy-L-threo-hexose
  参考文献：
  名称：

  由L-谷氨酸合成d-氨基糖和L-若丹糖

  摘要：

  摘要通过涉及转化为（S）-γ-羧基-γ-丁内酯（2），转化为2，通过重氮酮途径将2转化为相应的甲基酮，然后用硼氢化锌或硼烷-甲基硫醚选择性还原。用氢化二异丁基铝还原两个内酯得到相应的脱氧糖。尽管制备2的方法有所改进，但该步骤的光学收率仅为约80％，但从氯仿中结晶一次后，其光学纯度提高到96％。随后的步骤仅产生4％的光学纯度损失。

  DOI：

  10.1016/0008-6215(83)88353-0
• 作为产物：
  描述：

  L-古洛糖酸-gamma-内酯 在 palladium on activated charcoal 氢溴酸 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 71.0h， 生成 (S)-5-((S)-1-hydroxyethyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Pedersen, Christian; Schubert, Lene, Acta Chemica Scandinavica, 1993, vol. 47, # 9, p. 885 - 888

  摘要：

  DOI：

文献信息

• INACTIVATORS OF TOXOPLASMA GONDII ORNITHINE AMINOTRANSFERASE FOR TREATING TOXOPLASMOSIS AND MALARIA
  申请人：Northwestern University

  公开号：US20180098952A1

  公开（公告）日：2018-04-12

  Disclosed are methods, compounds, and compositions for treating infection by an Apicomplexan parasite that include administering a compound that selectively inactivates ornithine aminotransferase of the Apicomplexan parasite. Specifically, the methods, compounds, compounds may be utilized for treating infection by Toxoplasma gondii and toxoplasmosis and for treating infection by Plasmodium falciparum and malaria. The compounds disclosed herein are observed to selectively inactivate Toxoplasma gondii ornithine aminotransferase (TgOAT) relative to human OAT and relative to human γ-aminobutyric aminotransferase (GABA-AT).

  揭示了一种治疗具有选择性灭活裂殖孢子虫的鸟氨基转移酶的化合物、方法和组合物。具体来说，这些方法、化合物可用于治疗弓形虫和弓形虫病感染，以及治疗疟原虫和疟疾感染。本文披露的化合物被观察到相对于人类鸟氨基转移酶和人类γ-氨基丁酸氨基转移酶（GABA-AT）具有选择性地灭活弓形虫鸟氨基转移酶（TgOAT）。
• A simple, general distereoselective synthesis of 5-hydroxyalkylbutan-4-olides
  作者：Charles W. Jefford、Ying Wang

  DOI：10.1039/c39870001513

  日期：——

  cis- and trans-Hex-4-enoic acids and their 6-n-propyl and n-butyl derivatives, when treated with a 1.1 molar excess of m-chloroperbenzoic acid and Amberlyst-15 as catalyst in CH2Cl2 at 20 °C, gave the corresponding threo- and erythro-5-hydroxyalkylbutan-4-olides in quantitative yields.

  顺式-和反式-己-4-烯羧酸和它们的6-正丙基和正丁基的衍生物，当与1.1摩尔过量的处理米氯过苯甲酸和Amberlyst-15作为催化剂的在CH 2氯2在20℃ C，以定量收率得到相应的苏-和赤--5-羟基烷基丁烷-4-醇化物。
• Ru-Catalyzed Isomerization of Achmatowicz Derivatives: A Sustainable Route to Biorenewables and Bioactive Lactones
  作者：Miroslav Dangalov、Adolfo Fernández-Figueiras、Martin A. Ravutsov、Ekaterina Vakarelska、Maya K. Marinova、Nuno R. Candeias、Svilen P. Simeonov

  DOI：10.1021/acscatal.2c04867

  日期：2023.2.3

  A Ru-catalyzed isomerization of Achmatowicz derivatives that opens unexplored routes to diversify the biogenic furanic platform is reported. The mechanistic insights of this formally redox-neutral intramolecular process were studied computationally and by deuterium labeling. The transformation proved to be a robust synthetic tool to achieve the synthesis of bioderived-monomers and a series of 4-keto-δ-valerolactones

  报道了 Achmatowicz 衍生物的 Ru 催化异构化，该异构化开辟了使生物源呋喃平台多样化的未开发途径。通过计算和氘标记研究了这种正式的氧化还原中性分子内过程的机理见解。该转化被证明是一种强大的合成工具，可实现生物衍生单体和一系列 4-酮基-δ-戊内酯的合成，进一步促进了合成乙酰基合成的灵活策略的发展。还描述了两种天然产物（即 ( S , S )-muricatacin 和 ( S , S )-L-因子）的简洁且无保护基团的不对称全合成。
• Stereochemically controlled intramolecular Diels–Alder reactions: synthesis of substituted trans-fused octahydronaphthalenes possessing a bridgehead methyl group
  作者：Alan H. Davidson、Brian A. Moloney

  DOI：10.1039/c39890000445

  日期：——

  Cyclisation of triene (5) gives solely the octahydronaphthalene (9).

  三烯（5）的环化仅产生八氢萘（9）。
• Probing the steric requirements of the γ-aminobutyric acid aminotransferase active site with fluorinated analogues of vigabatrin
  作者：Jose I. Juncosa、Andrew P. Groves、Guoyao Xia、Richard B. Silverman

  DOI：10.1016/j.bmc.2012.12.009

  日期：2013.2

  We have synthesized three analogues of 4-amino-5-fluorohexanoic acids as potential inactivators of gamma-aminobutyric acid aminotransferase (GABA-AT), which were designed to combine the potency of their shorter chain analogue, 4-amino-5-fluoropentanoic acid (AFPA), with the greater enzyme selectivity of the antiepileptic vigabatrin (Sabril (R)). Unexpectedly, these compounds failed to inactivate or inhibit the enzyme, even at high concentrations. On the basis of molecular modeling studies, we propose that the GABA-AT active site has an accessory binding pocket that accommodates the vinyl group of vigabatrin and the fluoromethyl group of AFPA, but is too narrow to support the extra width of the distal methyl group in the synthesized analogues. (C) 2012 Elsevier Ltd. All rights reserved.