(1S,2R,3R)-1-methyl-cyclopentane-1,2,3-triol | 918403-89-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3R)-1-methyl-cyclopentane-1,2,3-triol
• 英文别名: (1S,2R,3R)-1-Methylcyclopentane-1,2,3-triol；(1S,2R,3R)-1-methylcyclopentane-1,2,3-triol
• CAS: 918403-89-1
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: WRVWZOOJULPXAG-PBXRRBTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3aS,6aS)-3a-hydroxy-2,2,6a-trimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one 在 sodium tetrahydroborate 、 硫酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.5h， 生成 (1S,2R,3R)-1-methyl-cyclopentane-1,2,3-triol
  参考文献：
  名称：

  Synthesis of chiral hydroxylated cyclopentanones and cyclopentanes

  摘要：

  A method for the synthesis of enantiomeric 1,3-dihydroxy and 2,3-dihydroxy cyclopentanones, starting from a commercially available 3-methyl-cyclopentane-1,2-dione 1, is described. Dione 1 was subjected to asymmetric 3-hydroxylation to afford 3-methyl-3hydroxy-1,2-dione 2. The carbonyl groups in 2 were selectively differentiated by converting them either in dimethylacetal 5 or acetonide 6. Stereoselective reduction of those acetals by using NaBH4 afforded chiral methyl 1,2-dihydroxy cyclopentanone 9 and 1,3-dihydroxy cyclopentanone 10, respectively. The diols obtained were further converted to the corresponding diastereomeric triols 11-13 by hydride reduction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.015

文献信息

• Probing Autoinducer-2 Based Quorum Sensing: The Biological Consequences of Molecules Unable To Traverse Equilibrium States
  作者：Kyoji Tsuchikama、Colin A. Lowery、Kim D. Janda

  DOI：10.1021/jo200882k

  日期：2011.9.2

  in either V. harveyi or S. typhimurium assay, whereas weak to moderate antagonists were found against V. harveyi. On the basis of NMR analyses and DFT calculations, the heterocyclic oxygen atom within DPD appears necessary to promote hydration at the C3 position of cyclic DPD to afford the active tetrahydroxy species. These results also shed light on the interaction between the heterocyclic oxygen atom

  细菌已经开发出一种细胞间通讯系统，称为群体感应（QS），它可以通过交换化学信号来实现群体依赖性的行为协调。自诱导剂-2 (AI-2) 是一类源自 4,5-二羟基-2,3-戊二酮 (DPD) 的 QS 信号，已被证明是多种细菌物种中的通用信号分子。尽管人们对此很感兴趣，但基于 AI-2 的 QS 系统的研究仍然是一个具有挑战性的课题，部分原因是 DPD 的线性和循环形式之间的快速相互转换。在此，我们报告了 DPD 碳环类似物的有效合成的设计和开发，这些类似物被锁定在环状形式。评估了合成类似物对哈维弧菌和鼠伤寒沙门氏菌中基于 AI-2 的 QS 的调节作用。在哈维氏弧菌或鼠伤寒沙门氏菌测定中均未发现激动剂，而针对哈维氏弧菌发现了弱至中度的拮抗剂。根据 NMR 分析和 DFT 计算，DPD 中的杂环氧原子似乎对于促进环状 DPD C3 位置的水合以提供活性四羟基物质是必需的。这些结果还揭示了杂环氧原子和受体蛋白之间的相互作用，以及
• Synthesis of chiral hydroxylated cyclopentanones and cyclopentanes
  作者：Allan Niidu、Anne Paju、Margus Eek、Aleksander-Mati Müürisepp、Tõnis Pehk、Margus Lopp

  DOI：10.1016/j.tetasy.2006.09.015

  日期：2006.10

  A method for the synthesis of enantiomeric 1,3-dihydroxy and 2,3-dihydroxy cyclopentanones, starting from a commercially available 3-methyl-cyclopentane-1,2-dione 1, is described. Dione 1 was subjected to asymmetric 3-hydroxylation to afford 3-methyl-3hydroxy-1,2-dione 2. The carbonyl groups in 2 were selectively differentiated by converting them either in dimethylacetal 5 or acetonide 6. Stereoselective reduction of those acetals by using NaBH4 afforded chiral methyl 1,2-dihydroxy cyclopentanone 9 and 1,3-dihydroxy cyclopentanone 10, respectively. The diols obtained were further converted to the corresponding diastereomeric triols 11-13 by hydride reduction. (c) 2006 Elsevier Ltd. All rights reserved.