Endo-methyl 7-oxabicyclo[2.2.1]heptane-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: Endo-methyl 7-oxabicyclo[2.2.1]heptane-2-carboxylate
• 英文别名: methyl (1S,2S,4R)-7-oxabicyclo[2.2.1]heptane-2-carboxylate
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: UYMKMUZNHJKUQB-VQVTYTSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Endo-methyl 7-oxabicyclo[2.2.1]heptane-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以89%的产率得到(+)-endo-2-Hydroxymethyl-7-oxabicyclo<2.2.1>heptane
  参考文献：
  名称：

  第一个有效的不对称合成7-氧杂双环[2.2.1]庚-5-烯-2-羧酸酯衍生物

  摘要：

  通过（S）s-和（R）s -3-（2-吡啶基亚磺酰基）的高度非对映选择性Diels-Alder反应，完成7-氧杂双环[2.2.1]庚-5-烯-2-羧酸酯衍生物的非对称合成）与呋喃的丙烯酸酯。

  DOI：

  10.1039/c39860000771
• 作为产物：
  描述：

  7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 Endo-methyl 7-oxabicyclo[2.2.1]heptane-2-carboxylate
  参考文献：
  名称：

  高压有机化学。V. 呋喃与丙烯酸酯和马来酸酯的 Diels-Alder 反应

  摘要：

  已经在高压条件下研究了呋喃与丙烯酸酯和马来酸酯的一系列 Diels-Alder 反应。丙烯酸和聚合物的加合物的近似内/外比率...

  DOI：

  10.1246/bcsj.55.496

文献信息

• The Exocyclic Effect:  Protecting Group Strategy to Enhance Stereoselectivity in Hydrogen Transfer Reactions of Acyclic Free Radicals
  作者：Yvan Guindon、Anne-Marie Faucher、Élyse Bourque、Valérie Caron、Grace Jung、Serge R. Landry

  DOI：10.1021/jo971595s

  日期：1997.12.1

  To enhance the diastereoselectivity of the hydrogen transfer reaction of acyclic substrates bearing 1,2- or 1,3-diols, the feasibility of a strategy employing bifunctional protecting groups has been demonstrated. This strategy is based upon the "exocyclic effect" or the significant improvement of anti-selectivity exhibited by the reductions of substrates in which the two substituents (R-1 and Y) at the stereogenic center alpha to the radical center are linked together. A rationale for the excellent facial discrimination of these exocyclic radicals is offered based on an analysis of transition state models, which considers both steric and electronic factors.
• High Pressure Organic Chemistry. V. Diels-Alder Reactions of Furan with Acrylic and Maleic Esters
  作者：Hiyoshizo Kotsuki、Hitoshi Nishizawa、Masamitsu Ochi、Kiyoshi Matsuoka

  DOI：10.1246/bcsj.55.496

  日期：1982.2

  A series of Diels-Alder reactions of furan with acrylic and maleic esters has been investigated under conditions of high pressure. The approximate endo/exo ratios of the adducts with acrylic and ma...

  已经在高压条件下研究了呋喃与丙烯酸酯和马来酸酯的一系列 Diels-Alder 反应。丙烯酸和聚合物的加合物的近似内/外比率...
• The first efficient asymmetric synthesis of 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate derivatives
  作者：Hiromitsu Takayama、Akira Iyobe、Toru Koizumi

  DOI：10.1039/c39860000771

  日期：——

  The asymmetic synthesis of 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate derivatives was accomplished by the highly diastereoselective Diels–Alder reaction of (S)s- and (R)s-3-(2-pyridylsulphinyl)acrylates with furan.

  通过（S）s-和（R）s -3-（2-吡啶基亚磺酰基）的高度非对映选择性Diels-Alder反应，完成7-氧杂双环[2.2.1]庚-5-烯-2-羧酸酯衍生物的非对称合成）与呋喃的丙烯酸酯。