D-allono-1,4-lactone | 29474-78-0

• 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: D-allono-1,4-lactone
• 英文别名: mannono-1,4-lactone；ascorbic acid；γ lactone of/the/ d-allonic acid；γ-Lacton der d-Allonsaeure；vitamin C；D-galactono-gamma-lactone；(3R,4S,5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one
• CAS: 29474-78-0
• 化学式: C₆H₁₀O₆
• 分子量: 178.142
• InChiKey: SXZYCXMUPBBULW-KKQCNMDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-allono-1,4-lactone 在 4-二甲氨基吡啶 、 对甲苯磺酸 吡啶 、 红铝 作用下， 以 四氢呋喃 、 邻苯二甲酸二甲酯 、 甲苯 为溶剂， 反应 2.0h， 生成 (1R)-(2,2-dimethyl-1,3-dioxolan-4-yl)-((4S,5S)-5-((methylsulfonyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate
  参考文献：
  名称：

  [EN] NOVEL DIHYDROXYPYRROLIDINE DERIVATIVES AS ANTI-CANCER AGENTS
  [FR] NOUVEAUX DÉRIVÉS DE DIHYDROXYPYRROLIDINE EN TANT QU'AGENTS ANTICANCÉREUX

  摘要：

  公开号：

  WO2009118712A3
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫化氢 作用下， 生成 D-allono-1,4-lactone
  参考文献：
  名称：

  Levene; Meyer, Journal of Biological Chemistry, 1916, vol. 26, p. 362

  摘要：

  DOI：
• 作为试剂：
  描述：

  、 paraquat dichloride 在 D-allono-1,4-lactone 作用下， 生成
  参考文献：
  名称：

  A new three-way supramolecular switch based on redox-controlled interconversion of hetero- and homo-guest-pair inclusion inside a host molecule

  摘要：

  A novel three-way supramolecular switch based on the interconversion of hetero-guest-pair (D–A) and homo-guest-pair (D2 or A2) inclusion inside cucurbit[8]uril is reported, which can be selectively controlled by chemical or electrochemical stimuli.

  DOI：

  10.1039/b818889k

文献信息

• De novo synthesis of 1-deoxythiosugars
  作者：Thanikachalam Gunasundari、Srinivasan Chandrasekaran

  DOI：10.1016/j.carres.2013.09.009

  日期：2013.12

  biologically potent and novel 1-deoxythiosugars is accomplished. Introduction of sulfur mediated by benzyltriethylammonium tetrathiomolybdate, as a sulfur transfer reagent through nucleophilic double displacement of tosylate in alpha,omega-di-O-tosyl aldonolactones in an intramolecular fashion is the key feature. The subsequent reduction of thiosugar lactones with borohydride exchange resin (BER) offers a

  完成了有效且新颖的具有生物活性的新型1-脱氧硫糖的化学合成。通过硫代甲酸酯以α，ω-二-O-甲苯磺酰基内酯内酯的亲核双取代以分子内方式引入作为硫转移剂的苄基三乙基铵四硫代钼酸铵是主要特征。随后用硼氢化物交换树脂（BER）还原硫糖内酯可提供许多脱氧硫糖，总收率良好。
• Regioselective Tosylation of Aldonolactones
  作者：Inge Lundt、Robert Madsen

  DOI：10.1055/s-1992-26320

  日期：——

  An investigation of the selective di-O-acylation with p-toluenesulfonyl (tosyl) chloride of the four D-pentono-, the eight D-hexono-and D-glycero-D-gulo-heptonolactone has been undertaken, and a number of 2,5-, 2,6- and 2,7-di-O-tosylated lactones have been prepared. Monotosylation of L-erythrono- and L-rhamnonolactone gave the corresponding 2-O-tosylates.

  对四种D-pentono、八种D-hexono和D-glycero-D-gulo-heptonolactone进行选择性二-O-酰化的研究已开展，并已制备出多种2,5-、2,6-和2,7-二-O-托烯基化的内酯。对L-红酮酸内酯和L-鼠李糖内酯的单托烯基化反应得到了相应的2-O-托烯基化产物。
• Effect of Cu addition to carbon-supported Ru catalysts on hydrogenation of alginic acid into sugar alcohols
  作者：Chunghyeon Ban、Seungdo Yang、Hyungjoo Kim、Do Heui Kim

  DOI：10.1016/j.apcata.2019.04.003

  日期：2019.5

  this study was to investigate the effect of Cu addition to carbon supported Ru catalysts on the hydrogenation of macroalgae-derived alginic acid into sugar alcohols, mainly sorbitol and mannitol. Both geometric and electronic effects were determined based on results of H2-TPR, H2- or CO-chemisorption, and XPS analyses after Cu was added to Ru. The addition of Cu to Ru caused blocking of active Ru surface

  这项研究的目的是研究将铜添加到碳载Ru催化剂中对大型藻类衍生的海藻酸氢化成糖醇（主要是山梨糖醇和甘露糖醇）的影响。根据H 2 -TPR，H 2的结果确定几何效应和电子效应-或CO化学吸附，以及将Cu添加到Ru中后进行XPS分析。在Ru中添加Cu会引起活性Ru表面的阻塞以及Ru与Cu之间的电子转移。Ru和Cu之间的紧密相互作用形成了RuCu双金属簇，加速了氢从Ru到Cu的溢出。当硝酸处理的活性炭上负载的5 wt％的Ru和1 wt％的Cu在180°C下反应2 h时，目标糖醇的最高收率为47.4％。由于铜沉积在催化剂上，RuCu双金属催化剂在重复反应后表现出失活。
• Levene; Jacobs, Chemische Berichte, 1910, vol. 43, p. 3147
  作者：Levene、Jacobs

  DOI：——

  日期：——
• Synthesis of 4,6-diamino-5-(polyhydroxyalkylamido)pyrimidines: conformation of the sugar chain
  作者：Derek Horton、Oscar Varela

  DOI：10.1016/s0008-6215(98)00078-0

  日期：1998.3

  Condensation of 4,5,6-triaminopyrimidine with ethyl glycolate, D-ribono-1,4-lactone, D-allono-1,4-lactone, D-glucono-1,5-lactone, and L-gulono-1,4-lactone led to the corresponding 4,6-diamino-5-(hydroxyalkylamido)pyrimidines (1a-e). The conformations in acidic aqueous solution of these acyclic carbohydrate derivatives were determined from the proton-proton NMR coupling constants at 300 MHz. The polyhydroxyalkyl chain of compounds 1b-e adopt sickle conformations in order to avoid the 1,3-parallel interactions between hydroxyl groups present in the planar zigzag conformer. Cyclization of 4,6-diamino-5-(hydroxyacetamido)pyrimidine (1a) afforded 8-(hydroxymethyl)adenine (2a), which was acetylated to give 2f. The C-13 NMR spectra of compounds 1a-e and 2a and f are also reported. (C) 1998 Elsevier Science Ltd. All rights reserved.