2-furyl (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate | 446035-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2-furyl (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
• 英文别名: furan-2-yl (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
• CAS: 446035-38-7
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: MTJUTGCENPLQQT-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-二溴-3-戊酮 、 2-furyl (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate 在 铜 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以12%的产率得到2,4-dimethyl-3-oxo-8-oxabicyclo[3.2.1]oct-6-en-1-yl (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
  参考文献：
  名称：

  Asymmetry induction on the [4C(4π)+3C(2π)] cycloaddition reaction of C2-functionalized furans: influence of the chiral auxiliary nature

  摘要：

  The study of the pi-facial diastereoselectivity in the [4+3] cycloaddition reaction of thirteen different chiral 2-substituted furans with oxyallyl cations, under sonochemical and/or thermal conditions, is presented. In almost all studied furans, a cis diastereoselectivity and a high endo diastereoselectivity is observed. Decreasing the distance between the closest stereocenter of the chiral auxiliary and the reactive C2-carbon of the furan ring, increases the pi-facial diastereoselectivity, especially by using chiral furyl-sulfoxides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00452-0
• 作为产物：
  描述：

  (1S)-(-)-莰烷酰氯 、 2(5H)-呋喃酮 在 三乙胺 作用下， 以 乙腈 为溶剂， 以52%的产率得到2-furyl (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
  参考文献：
  名称：

  Asymmetry induction on the [4C(4π)+3C(2π)] cycloaddition reaction of C2-functionalized furans: influence of the chiral auxiliary nature

  摘要：

  The study of the pi-facial diastereoselectivity in the [4+3] cycloaddition reaction of thirteen different chiral 2-substituted furans with oxyallyl cations, under sonochemical and/or thermal conditions, is presented. In almost all studied furans, a cis diastereoselectivity and a high endo diastereoselectivity is observed. Decreasing the distance between the closest stereocenter of the chiral auxiliary and the reactive C2-carbon of the furan ring, increases the pi-facial diastereoselectivity, especially by using chiral furyl-sulfoxides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00452-0

文献信息

• Induction of asymmetry on the [4+3] cycloaddition reaction of C2-functionalized furans
  作者：Angel M Montaña、Pedro M Grima

  DOI：10.1016/s0040-4039(02)00199-5

  日期：2002.3

  A study of the induction of asymmetry on the [4+3] cycloaddition reaction of some 13 C2-substituted furan derivatives with 2-oxyallyl cation is presented. The asymmetry was induced by a chiral auxiliary on C2 of furan. A vis diastereospecificity and a high endo diastereoselectivity are observed in almost all studied cases. On decreasing the distance between the stereocenter of the chiral auxiliary and the reactive C2-carbon of the furan ring, the pi-facial diastereoselectivity is increased. especially by using chiral furyl-sulfoxides. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Asymmetry induction on the [4C(4π)+3C(2π)] cycloaddition reaction of C2-functionalized furans: influence of the chiral auxiliary nature
  作者：Angel M Montaña、Pedro M Grima

  DOI：10.1016/s0040-4020(02)00452-0

  日期：2002.6

  The study of the pi-facial diastereoselectivity in the [4+3] cycloaddition reaction of thirteen different chiral 2-substituted furans with oxyallyl cations, under sonochemical and/or thermal conditions, is presented. In almost all studied furans, a cis diastereoselectivity and a high endo diastereoselectivity is observed. Decreasing the distance between the closest stereocenter of the chiral auxiliary and the reactive C2-carbon of the furan ring, increases the pi-facial diastereoselectivity, especially by using chiral furyl-sulfoxides. (C) 2002 Elsevier Science Ltd. All rights reserved.