cesium hydroxyacetate | 91364-47-5

• 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: cesium hydroxyacetate
• 英文别名: cesium glycolate；2-hydroxyacetic acid cesium salt；cesium;2-hydroxyacetate
• CAS: 91364-47-5
• 化学式: C₂H₃O₃*Cs
• 分子量: 207.949
• InChiKey: QDYKYXCGXHGJGO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -5.27
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cesium hydroxyacetate 、 在 18-冠醚-6 作用下， 以 甲苯 为溶剂， 反应 43.0h， 以57%的产率得到
  参考文献：
  名称：

  Bridgehead Modifications of Englerin A Reduce TRPC4 Activity and Intravenous Toxicity but not Cell Growth Inhibition

  摘要：

  Modifications at the bridgehead position of englerin A were made to explore the effects of variation at this site on the molecule for biological activity, as judged by the NCI 60 screen, in which englerin A is highly potent and selective for renal cancer cells. Replacement of the isopropyl group by other, larger substituents yielded compounds which displayed excellent selectivity and potency comparable to the natural product. Selected compounds were also evaluated for their effect on the ion channel TRPC4 as well as for intravenous toxicity in mice, and these had lower potency in both assays compared to englerin A.

  DOI：

  10.1021/acsmedchemlett.0c00186
• 作为产物：
  描述：

  羟基乙酸 在 caesium carbonate 作用下， 反应 0.5h， 以63%的产率得到cesium hydroxyacetate
  参考文献：
  名称：

  （±）-Englerin A及其截断类似物的全合成

  摘要：

  基于取代的吡啶鎓叶立德的1,3-偶极环加成反应，开发了（±）-Englerin A和许多截短的类似物的全合成。将双环烯酮支架进一步转化为截短的类似物和天然产物。桥头取代基对8-氧杂双环[3.2.1]辛烷的反应性的有趣的立体化学作用被发现。

  DOI：

  10.1002/ejoc.201801544

文献信息

• Asymmetric, Protecting-Group-Free Total Synthesis of (−)-Englerin A
  作者：Qianghui Zhou、Xiaofei Chen、Dawei Ma

  DOI：10.1002/anie.201000888

  日期：2010.5.3

  The golden touch: Total synthesis of natural (−)‐englerin A from (R)‐citronellal has been achieved using a gold‐catalyzed cyclization as the key step (see scheme). No protecting‐group manipulations were required in the synthetic sequence.

  黄金点：使用金催化环化作为关键步骤，可以从（R）-香茅醛中合成天然（-）-恩格尔林A。在合成序列中不需要保护基操作。
• Synthesis of α-Hydroxy Acids via Dehydrogenative Cross-Coupling of a Sustainable C₂ Chemical (Ethylene Glycol) with Alcohols
  作者：Mi-hyun Lee、Heemin Byeon、Hye-Young Jang

  DOI：10.1021/acs.joc.1c02981

  日期：2022.4.1

  (NHC, N-heterocyclic carbene)-catalyzed dehydrogenative coupling of sustainable ethylene glycol and various bioalcohols can produce industrially valuable α-hydroxy acids (AHAs). This study is the first to report the sustainable synthesis of higher Cn AHAs, in addition to glycolic acid (C2 AHA) and lactic acid (C3 AHA). This catalytic system can be recycled to the seventh cycle while maintaining good

  Ir(NHC)（NHC，N-杂环卡宾）催化的可持续乙二醇和各种生物醇的脱氢偶联可以产生具有工业价值的α-羟基酸（AHA）。本研究首次报道了除乙醇酸 (C 2 AHA) 和乳酸 (C 3 AHA) 之外更高 C n AHA 的可持续合成。该催化系统可以循环到第七个循环，同时保持良好的收率。基于18 O- 和2H-标记实验和电子喷雾电离质谱 (ESI-MS) 和 NMR 光谱分析。
• A Brief Synthesis of (−)-Englerin A
  作者：Zhenwu Li、Mika Nakashige、William J. Chain

  DOI：10.1021/ja201921j

  日期：2011.5.4

  Englerins A and B are guaiane sesquiterpenes that were isolated from the bark of Phyllanthus engleri, a plant indigenous to east Africa. The englerins consist of a 5-6-5 fused tricyclic structure with an ether bridge and two ester-bearing stereogenic centers, including a highly unusual glycolate residue. Englerin A is a potent and selective inhibitor of the growth of six human renal cancer cell lines. We report herein an efficient, eight-step synthesis of englerin A that leverages simple carbonyl-enabled carbon carbon bond formations. Our route is amenable to the production of a diverse series of analogues for structure function studies and determination of the mode of action of these natural products.
• Total Synthesis of (±)-Englerin A and Its Tuncated Analogues
  作者：Colleen Reagan、Graham Trevitt、Kirill Tchabanenko

  DOI：10.1002/ejoc.201801544

  日期：2019.2.7

  Total synthesis of (±)‐Englerin A and a number of truncated analogues was developed based on a 1,3‐dipolar cycloaddition of a substituted pyrylium ylide. The bicyclic enone scaffold was further converted into a truncated analogue and the natural product. Interesting stereochemical effects of the bridgehead substituents on the reactivity of the 8‐oxabicyclo[3.2.1]octanes were uncovered.

  基于取代的吡啶鎓叶立德的1,3-偶极环加成反应，开发了（±）-Englerin A和许多截短的类似物的全合成。将双环烯酮支架进一步转化为截短的类似物和天然产物。桥头取代基对8-氧杂双环[3.2.1]辛烷的反应性的有趣的立体化学作用被发现。
• Bridgehead Modifications of Englerin A Reduce TRPC4 Activity and Intravenous Toxicity but not Cell Growth Inhibition
  作者：Zhenhua Wu、Jean-Simon Suppo、Sarka Tumova、Jonathan Strope、Fernando Bravo、Melody Moy、Ethan S. Weinstein、Cody J. Peer、William D. Figg、William J. Chain、Antonio M. Echavarren、David J. Beech、John A. Beutler

  DOI：10.1021/acsmedchemlett.0c00186

  日期：2020.9.10

  Modifications at the bridgehead position of englerin A were made to explore the effects of variation at this site on the molecule for biological activity, as judged by the NCI 60 screen, in which englerin A is highly potent and selective for renal cancer cells. Replacement of the isopropyl group by other, larger substituents yielded compounds which displayed excellent selectivity and potency comparable to the natural product. Selected compounds were also evaluated for their effect on the ion channel TRPC4 as well as for intravenous toxicity in mice, and these had lower potency in both assays compared to englerin A.