7-methoxy-2,8-dioxabicyclo[5.3.0]decan-9-one | 253670-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 7-methoxy-2,8-dioxabicyclo[5.3.0]decan-9-one
• 英文别名: 8a-Methoxy-3,3a,5,6,7,8-hexahydrofuro[3,2-b]oxepin-2-one
• CAS: 253670-58-5
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: DVTYSUBLCKAVKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methoxy-2,8-dioxabicyclo[5.3.0]decan-9-one 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 以74%的产率得到2-(2-羟基乙基)-3-氧杂环庚烷醇
  参考文献：
  名称：

  The furan approach to oxacycles: synthesis of medium-size 2,3-disubstituted oxacycles

  摘要：

  We describe an efficient new approach for the synthesis of medium-size oxacycles that is based on the oxidation of a furan ring with singlet oxygen followed by an intramolecular Michael addition. This present study enlarges the scope of the furan approach strategy for the synthesis of oxepanes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.035
• 作为产物：
  描述：

  tert-butyl(4-(furan-2-yl)butoxy)diphenylsilane 在 oxygen 、 四丁基氟化铵 、 rose bengal 作用下， 以 四氢呋喃 为溶剂， 生成 7-methoxy-2,8-dioxabicyclo[5.3.0]decan-9-one
  参考文献：
  名称：

  The furan approach to oxacycles: synthesis of medium-size 2,3-disubstituted oxacycles

  摘要：

  We describe an efficient new approach for the synthesis of medium-size oxacycles that is based on the oxidation of a furan ring with singlet oxygen followed by an intramolecular Michael addition. This present study enlarges the scope of the furan approach strategy for the synthesis of oxepanes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.035

文献信息

• The Methoxyallene Approach to Oxacycles, Part 2: Stereoselective Synthesis of 2,3-Disubstituted Oxepanes
  作者：Yagamare Fall、Manuel Pérez、Pilar Canoa、Generosa Gómez、Marta Teijeira

  DOI：10.1055/s-2004-834946

  日期：——

  2,3-Disubstituted oxepanes 3 and 4 were stereoselectively synthesized from methoxyallene (1) and iodide 2. The trans stereochemistry of diol 3 was established by NMR studies of the bicyclic precursor 10, while the cis stereochemistry of 4 was secured by using the highly diastereoselective reducing agent L-Selectride.

  2,3-二取代的氧杂环丁烷 3 和 4 由甲氧基丙二烯 (1) 和碘化物 2 立体选择性合成。二醇 3 的反式立体化学是通过双环前体 10 的 NMR 研究确定的，而 4 的顺式立体化学是通过使用高度非对映选择性还原剂 L-Selectride。
• Synthesis of seven-membered oxacycles. Part 2: The furan approach
  作者：Yagamare Fall、Beatriz Vidal、David Alonso、Generosa Gómez

  DOI：10.1016/s0040-4039(03)01027-x

  日期：2003.6

  We describe an efficient new approach for the synthesis of seven-membered oxacycles that is based on the oxidation of a furan ring with singlet oxygen followed by an intramolecular Michael addition.

  我们描述了一种有效的新方法，用于合成七元氧杂环，它是基于呋喃环与单线态氧的氧化，然后是分子内迈克尔加成。
• Methoxyallene, a building block for the synthesis of seven-membered oxacycles
  作者：Yagamare Fall、Generosa Gomez、Carlos Fernandez

  DOI：10.1016/s0040-4039(99)01778-5

  日期：1999.11

  An efficient new approach for the synthesis of seven-membered oxacycles is described. (C) 1999 Elsevier Science Ltd. All rights reserved.
• The furan approach to oxacycles: synthesis of medium-size 2,3-disubstituted oxacycles
  作者：Manuel Pérez、Pilar Canoa、Generosa Gómez、Carmen Terán、Yagamare Fall

  DOI：10.1016/j.tetlet.2004.05.035

  日期：2004.6

  We describe an efficient new approach for the synthesis of medium-size oxacycles that is based on the oxidation of a furan ring with singlet oxygen followed by an intramolecular Michael addition. This present study enlarges the scope of the furan approach strategy for the synthesis of oxepanes. (C) 2004 Elsevier Ltd. All rights reserved.