5-bromo-3-methyl-2H-pyran-2-one | 26454-75-1

• 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-3-methyl-2H-pyran-2-one
• 英文别名: 3-methyl-5-bromo-2-pyrone；5-bromo-3-methyl-pyran-2-one；5-Brom-3-methyl-pyron-(2)；5-bromo-3-methylpyran-2-one
• CAS: 26454-75-1
• 化学式: C₆H₅BrO₂
• 分子量: 189.008
• InChiKey: YNSFWEGTKPQDSF-UHFFFAOYSA-N

物化性质

• 沸点：
  232.7±33.0 °C(Predicted)
• 密度：
  1.704±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  5-bromo-3-methyl-2H-pyran-2-one 在 咪唑 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 36.33h， 生成 (1S,6R)-3-Bromo-1,6-dimethyl-4-oxo-cyclohex-2-enecarbaldehyde
  参考文献：
  名称：

  Regioselective Pd-Catalyzed Synthesis and Application of 3-Methyl-5-bromo-2-pyrone toward Keto-phomactin A

  摘要：

  An efficient one-step synthetic protocol for 3-methyl-5-bromo-2-pyrone was developed using the C3-selective Pd-catalyzed coupling reaction of 3,5-dibromo-2-pyrone with Me3Al-dimethylaminoethanol complex. A subsequent seven-step reaction sequence provided a cyclohexenyl bromide, which served as the key intermediate for the synthesis of the keto analogue of phomactin A, in 31% overall yield.

  DOI：

  10.1021/ol061231z
• 作为产物：
  描述：

  3-甲基吡喃-2-酮 在 溴 、 三乙胺 作用下， 生成 5-bromo-3-methyl-2H-pyran-2-one
  参考文献：
  名称：

  A new synthesis of alkylated 2H-pyran-2-ones and its application to the determination of the relative and absolute configuration of supellapyrone, sex pheromone of the brownbanded cockroach, Supella longipalpa

  摘要：

  The sex pheromone of the brownbanded cockroach, Supella longipalpa, can be synthesized by direct coupling of a brominated pyrone with an alkylzinc reagent. The stereochemistry of the natural pheromone has been assigned as (2'R, 4'R)-5-(2',4'-dimethylheptanyl)-3-methyl-2H-pyran-2-one by a combination of synthesis, chiral gas chromatography, and electrophysiological measurement.

  DOI：

  10.1016/0040-4039(94)02214-v

文献信息

• Total Syntheses of Ningalins D and G
  作者：Jang-Yeop Kim、Dong-Hyun Kim、Tae-Hong Jeon、Woo-Hyung Kim、Cheon-Gyu Cho

  DOI：10.1021/acs.orglett.7b02372

  日期：2017.9.1

  A flexible synthetic strategy for the total syntheses of ningalins D and G is described. The highly effective TMS-OTf/2,6-lutidine-mediated [3,3]-sigmatropic rearrangement of densely loaded dinaphthyl hydrazides and cyclization of the resulting 2,2′-diamino-1,1′-dinaphthyls afforded the key 7H-dibenzo[c,g]carbazole intermediates. Successful conversions to biphenylene quinone methides followed by regioselective

  描述了一种灵活的合成策略，用于合成宁格灵D和G。高效TMS-光学传递函数/ 2,6-二甲基吡啶-介导的[3,3]密集负载二萘基酰肼，并将所得的2,2'-二氨基-1,1'- dinaphthyls得到钥匙7的环化的重排-sigmatropic ħ -二苯并[ c，g ]咔唑中间体。成功地转化为联苯醌甲基化物，然后进行区域选择性溴化，完成了标题海洋生物碱的全部合成。
• Regioselective Pd-Catalyzed Synthesis and Application of 3-Methyl-5-bromo-2-pyrone toward Keto-phomactin A
  作者：Kimoon Ryu、Young-Suk Cho、Soo-Im Jung、Cheon-Gyu Cho

  DOI：10.1021/ol061231z

  日期：2006.7.1

  An efficient one-step synthetic protocol for 3-methyl-5-bromo-2-pyrone was developed using the C3-selective Pd-catalyzed coupling reaction of 3,5-dibromo-2-pyrone with Me3Al-dimethylaminoethanol complex. A subsequent seven-step reaction sequence provided a cyclohexenyl bromide, which served as the key intermediate for the synthesis of the keto analogue of phomactin A, in 31% overall yield.
• A new synthesis of alkylated 2H-pyran-2-ones and its application to the determination of the relative and absolute configuration of supellapyrone, sex pheromone of the brownbanded cockroach, Supella longipalpa
  作者：Xiongwei Shi、Walter Soares Leal、Zhi Liu、Eric Schrader、Jerrold Meinwald

  DOI：10.1016/0040-4039(94)02214-v

  日期：1995.1

  The sex pheromone of the brownbanded cockroach, Supella longipalpa, can be synthesized by direct coupling of a brominated pyrone with an alkylzinc reagent. The stereochemistry of the natural pheromone has been assigned as (2'R, 4'R)-5-(2',4'-dimethylheptanyl)-3-methyl-2H-pyran-2-one by a combination of synthesis, chiral gas chromatography, and electrophysiological measurement.