(Z)-(4aS,9aR)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxabenzocycloheptene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (Z)-(4aS,9aR)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxabenzocycloheptene
• 英文别名: (4aS,9aR)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepine
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: LLVHRJJNGOFRST-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2'R,3'S)-(3'-allyloxytetrahydropyran-2'-yl)acetonitrile 在 bis(tricyclohexylphosphine)benzylidine ruthenium(IV) di 、 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (Z)-(4aS,9aR)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxabenzocycloheptene
  参考文献：
  名称：

  Ring-Closing Metathesis in the Synthesis of Large and Medium-Sized Oxacycles. Application to the Synthesis of Polyoxygenated Macrocycles

  摘要：

  Ring-closing olefin metathesis (RCM) catalyzed by Grubbs's ruthenium benzylidene complex 1 is applied to the synthesis of unsaturated rings ranging in size from seven to thirteen members in trans-fused polyether systems. Reaction occurs with great efficiency in the cyclization of oxepene and oxocene rings, but as ring size increases, yields drop. The influence of the final double bond position is also studied. Better yields and milder reaction conditions are observed when an additional oxygen atom is introduced on the diene. This feature has promoted the application of this reaction to the synthesis of polyoxygenated macrocycles (with sizes ranging from 15 to 21 members), with excellent results.

  DOI：

  10.1021/jo9901438

文献信息

• A concise synthesis of ortho-condensed oxane-oxene, oxepene, oxocene and oxonene ring systems
  作者：Eleuterio Alvarez、Mercedes Delgado、María Teresa Díaz、Liu Hanxing、Ricardo Pérez、Julio D. Martín

  DOI：10.1016/0040-4039(96)00408-x

  日期：1996.4

  An efficient strategy for the synthesis of trans-fused oxabicyclic systems involving thioannulation followed by a Ramberg-Bäcklund olefination as the key step is described.

  描述了一种有效的合成策略，该方法涉及包括硫代环化，随后的Ramberg-Bäcklund烯化为关键步骤的反式氧杂双环系统的合成。
• Ring-Closing Metathesis in the Synthesis of Large and Medium-Sized Oxacycles. Application to the Synthesis of Polyoxygenated Macrocycles
  作者：Mercedes Delgado、Julio D. Martín

  DOI：10.1021/jo9901438

  日期：1999.6.1

  Ring-closing olefin metathesis (RCM) catalyzed by Grubbs's ruthenium benzylidene complex 1 is applied to the synthesis of unsaturated rings ranging in size from seven to thirteen members in trans-fused polyether systems. Reaction occurs with great efficiency in the cyclization of oxepene and oxocene rings, but as ring size increases, yields drop. The influence of the final double bond position is also studied. Better yields and milder reaction conditions are observed when an additional oxygen atom is introduced on the diene. This feature has promoted the application of this reaction to the synthesis of polyoxygenated macrocycles (with sizes ranging from 15 to 21 members), with excellent results.