(1R,3S)-4-cyclopentene-1,3-dimethanol monoacetate | 141352-50-3

• 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: (1R,3S)-4-cyclopentene-1,3-dimethanol monoacetate
• 英文别名: [(1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl]methyl acetate
• CAS: 141352-50-3
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: IAALUCYUZVBOAX-BDAKNGLRSA-N

物化性质

• 沸点：
  250.9±13.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (1R,3S)-4-cyclopentene-1,3-dimethanol monoacetate 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Enzymatic asymmetric synthesis of cis-4-cyclopentene-1,3-dimethanol monoacetate.

  摘要：

  Asymmetric synthesis of cis-4-cyclopentene-1,3-dimethanol monoacetate was performed via enzymatic hydrolysis of the diacetate or enzymatic acetylation of the diol precursor. Esterases and lipases were studied, and Candida cylindracea lipase was shown to afford the (-)-enantiomer with ee > 97%.

  DOI：

  10.1016/s0957-4166(00)80286-4
• 作为产物：
  描述：

  cis-3,5-bis(hydroxymethylene)cyclopent-4-ene 在 吡啶 、 水 作用下， 反应 36.0h， 生成 (1R,3S)-4-cyclopentene-1,3-dimethanol monoacetate
  参考文献：
  名称：

  Enzymatic asymmetric synthesis of cis-4-cyclopentene-1,3-dimethanol monoacetate.

  摘要：

  Asymmetric synthesis of cis-4-cyclopentene-1,3-dimethanol monoacetate was performed via enzymatic hydrolysis of the diacetate or enzymatic acetylation of the diol precursor. Esterases and lipases were studied, and Candida cylindracea lipase was shown to afford the (-)-enantiomer with ee > 97%.

  DOI：

  10.1016/s0957-4166(00)80286-4

文献信息

• Synthesis of Natural-Product-Like Molecules with Over Eighty Distinct Scaffolds
  作者：Daniel Morton、Stuart Leach、Christopher Cordier、Stuart Warriner、Adam Nelson

  DOI：10.1002/anie.200804486

  日期：2009.1

  Seeking scaffold diversity: A synthetic approach for the combinatorial variation of the scaffolds of small molecules is described. Using just six basic reaction types, compounds with 84 distinct scaffolds were prepared. The compounds had many natural‐product‐like structural features including rich stereochemistry, heterocyclic and unsaturated ring systems, and dense functionalization.

  寻求支架多样性：描述了小分子支架组合变异的合成方法。仅使用六种基本反应类型，就制备了具有 84 种不同支架的化合物。这些化合物具有许多类似于天然产物的结构特征，包括丰富的立体化学、杂环和不饱和环系统以及密集的官能化。
• Synthesis of Small Molecules with High Scaffold Diversity: Exploitation of Metathesis Cascades in Combination with Inter- and Intramolecular Diels-Alder Reactions
  作者：Catherine O'Leary-Steele、Palle J. Pedersen、Thomas James、Thomas Lanyon-Hogg、Stuart Leach、Jerome Hayes、Adam Nelson

  DOI：10.1002/chem.201000707

  日期：2010.8.16

  synthetic accessibility of small molecules. Historically, however, chemists have explored chemical space in an exceptionally uneven and unsystematic way. We have previously demonstrated that metathesis cascade chemistry may be harnessed to yield small molecule collections with high scaffold diversity. Here, we describe the extent to which inter‐ and intramolecular Diels–Alder reactions, when used in conjunction

  我们对化学空间区域生物学相关性的了解很大程度上取决于小分子的合成可及性。但是，从历史上看，化学家们以一种异常不平衡且不系统的方式来探索化学空间。我们以前已经证明，复分解级联化学可以被利用来产生具有高支架多样性的小分子集合。在这里，我们描述了分子间和分子内Diels-Alder反应与易位级联结合使用时，在多大程度上可以扩展分子支架的范围。由两个或三个构件的组合制备了一系列复分解底物。利用复分解级联来“重新编程”分子支架。在许多情况下，复分解产物为1,3-二烯，它们是分子间或分子内Diels-Alder反应的潜在底物。通常通过荧光标记来促进产品的合成和功能化，例如通过使用我们开发的“安全捕获”连接子。结果表明，在某些情况下，Diels–Alder反应可以扩展使用复分解级联反应制备的分子支架的范围。
• [EN] GABAPENTIN ANALOGUES FOR FIBROMYALGIA AND OTHER RELATED DISORDERS<br/>[FR] ANALOGUES DE GABAPENTINE POUR LE TRAITEMENT DE LA FIBROMYALGIE ET D'AUTRES TROUBLES CONNEXES
  申请人：WARNER LAMBERT CO

  公开号：WO2004054564A1

  公开（公告）日：2004-07-01

  This invention provides new uses for compounds of Formula (I) or Formula (II) or a pharmaceutically acceptable salt thereof for the treatment of fibromyalgia and other disorders.