5-Bromo-2-methyl-2,3-dihydropyran-6-one | 1266674-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 5-Bromo-2-methyl-2,3-dihydropyran-6-one
• 英文别名: 5-bromo-2-methyl-2,3-dihydropyran-6-one
• CAS: 1266674-99-0
• 化学式: C₆H₇BrO₂
• 分子量: 191.024
• InChiKey: GWAXGOJVEZXQDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-呋甲醚 、 5-Bromo-2-methyl-2,3-dihydropyran-6-one 在 氯化铪 作用下， 以 1,2-二氯乙烷 为溶剂， 以32%的产率得到
  参考文献：
  名称：

  The second generation synthesis of (+)-pseudodeflectusin

  摘要：

  The second generation synthesis of (+)-pseudodeflectusin (1), a potential antitumor agent, has been achieved. The key synthetic step is the cascade reaction involving Diels-Alder reaction, lactonization, and decarboxylation to give cycloadduct 6 with complete regioselectivity in good yield. We found that NaH is the best base to facilitate the Diels-Alder reaction of hydroxypyrone 7 with alkyne 8. The present synthetic route enables the total synthesis of (+)-1 in only five-steps from the known compounds 7 and 8. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.153

文献信息

• The second generation synthesis of (+)-pseudodeflectusin
  作者：Yuna Sato、Kouji Kuramochi、Takahiro Suzuki、Atsuo Nakazaki、Susumu Kobayashi

  DOI：10.1016/j.tetlet.2010.11.153

  日期：2011.2

  The second generation synthesis of (+)-pseudodeflectusin (1), a potential antitumor agent, has been achieved. The key synthetic step is the cascade reaction involving Diels-Alder reaction, lactonization, and decarboxylation to give cycloadduct 6 with complete regioselectivity in good yield. We found that NaH is the best base to facilitate the Diels-Alder reaction of hydroxypyrone 7 with alkyne 8. The present synthetic route enables the total synthesis of (+)-1 in only five-steps from the known compounds 7 and 8. (C) 2010 Elsevier Ltd. All rights reserved.