(2R,3R)-2-[(E)-2-bromovinyl]-2,3,4,5-tetrahydro-5,5-dimethoxy-2-methylfuran-3-ol | 1301680-49-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-2-[(E)-2-bromovinyl]-2,3,4,5-tetrahydro-5,5-dimethoxy-2-methylfuran-3-ol
• 英文别名: (2R,3R)-2-[(E)-2-bromoethenyl]-5,5-dimethoxy-2-methyloxolan-3-ol
• CAS: 1301680-49-8
• 化学式: C₉H₁₅BrO₄
• 分子量: 267.12
• InChiKey: UIZLVBUNVIEBTR-IVZJMYDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-[(E)-2-bromovinyl]-2,3,4,5-tetrahydro-5,5-dimethoxy-2-methylfuran-3-ol 在 四(三苯基膦)钯 、 甲烷 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.08h， 生成 (R)-2-[(E,E)-hexa-1,3-dienyl]-5-methoxy-2-methylfuran-3(2H)-one
  参考文献：
  名称：

  A Serendipitous Synthesis of (+)-Gregatin B, Second Structure Revisions of the Aspertetronins, Gregatins, and Graminin A, Structure Revision of the Penicilliols

  摘要：

  A (DHQN)(2)AQN-promoted asymmetric dihydroxylation (92% ee) of the allyl chloride derived from enynol (E)-13 and an 8-step sequence provided access to the hydroxyethylated furanone (R)-21. Oxidation with MnO(2) furnished 50% furanone (+)-(R)-2a and 2.7% isomeric furanone (+)-(R)-3a. (R)-2a possesses the accepted constitution of (+)-gregatin B but its spectra are different. Surprisingly, (+)-(R)-3a equals the natural product. Analogous structure reassignments are due for the gregatins A and C-E, the aspertetronins A-B, graminin A, and the penicilliols A and B.

  DOI：

  10.1021/ol2008318
• 作为产物：
  描述：

  (2R,3R)-2,3,4,5-tetrahydro-5,5-dimethoxy-2-methyl-2-[(E)-2-(tributylstannyl)vinyl]furan-3-ol 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以84%的产率得到(2R,3R)-2-[(E)-2-bromovinyl]-2,3,4,5-tetrahydro-5,5-dimethoxy-2-methylfuran-3-ol
  参考文献：
  名称：

  A Serendipitous Synthesis of (+)-Gregatin B, Second Structure Revisions of the Aspertetronins, Gregatins, and Graminin A, Structure Revision of the Penicilliols

  摘要：

  A (DHQN)(2)AQN-promoted asymmetric dihydroxylation (92% ee) of the allyl chloride derived from enynol (E)-13 and an 8-step sequence provided access to the hydroxyethylated furanone (R)-21. Oxidation with MnO(2) furnished 50% furanone (+)-(R)-2a and 2.7% isomeric furanone (+)-(R)-3a. (R)-2a possesses the accepted constitution of (+)-gregatin B but its spectra are different. Surprisingly, (+)-(R)-3a equals the natural product. Analogous structure reassignments are due for the gregatins A and C-E, the aspertetronins A-B, graminin A, and the penicilliols A and B.

  DOI：

  10.1021/ol2008318

文献信息

• A Serendipitous Synthesis of (+)-Gregatin B, Second Structure Revisions of the Aspertetronins, Gregatins, and Graminin A, Structure Revision of the Penicilliols
  作者：Heike Burghart-Stoll、Reinhard Brückner

  DOI：10.1021/ol2008318

  日期：2011.5.20

  A (DHQN)(2)AQN-promoted asymmetric dihydroxylation (92% ee) of the allyl chloride derived from enynol (E)-13 and an 8-step sequence provided access to the hydroxyethylated furanone (R)-21. Oxidation with MnO(2) furnished 50% furanone (+)-(R)-2a and 2.7% isomeric furanone (+)-(R)-3a. (R)-2a possesses the accepted constitution of (+)-gregatin B but its spectra are different. Surprisingly, (+)-(R)-3a equals the natural product. Analogous structure reassignments are due for the gregatins A and C-E, the aspertetronins A-B, graminin A, and the penicilliols A and B.