3-(hydroxymethyl)-4-methoxy-6-methyl-2H-pyran-2-one | 218435-67-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-(hydroxymethyl)-4-methoxy-6-methyl-2H-pyran-2-one
• 英文别名: 3-(Hydroxymethyl)-4-methoxy-6-methylpyran-2-one
• CAS: 218435-67-7
• 化学式: C₈H₁₀O₄
• 分子量: 170.165
• InChiKey: CDFPHNABWPDHQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(hydroxymethyl)-4-methoxy-6-methyl-2H-pyran-2-one 在 4-甲基苯磺酸吡啶 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 6-((7E,9E)-2-Hydroxy-undeca-7,9-dienyl)-4-methoxy-3-(tetrahydro-pyran-2-yloxymethyl)-pyran-2-one
  参考文献：
  名称：

  Total Synthesis of (−)-Solanapyrone A via Enzymatic Diels−Alder Reaction of Prosolanapyrone

  摘要：

  The syntheses of prosolanapyrones I (6) and II (7) via the aldol reactions of pyrone and dienal segments have been achieved in five steps in 31% overall yield for 6 and seven steps in 5% overall yield for 7. An improved synthetic route starting from vinylpyrone 27 provided 7 in 11 steps in 12% overall yield. The enzymatic Diels-Alder reaction of 7 affords (-)-solanapyrone A (1) with high enantioselectivity and with good exo-selectivity, which is difficult to attain by chemical methods. In addition, a crude enzyme preparation from Alternaria solani has been used to perform a kinetic resolution of(+/-)-3.

  DOI：

  10.1021/jo980743r
• 作为产物：
  描述：

  4-甲氧基-6-甲基-2H-吡喃酮 在 sodium tetrahydroborate 、 四氯化钛 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 3-(hydroxymethyl)-4-methoxy-6-methyl-2H-pyran-2-one
  参考文献：
  名称：

  Total Synthesis of (−)-Solanapyrone A via Enzymatic Diels−Alder Reaction of Prosolanapyrone

  摘要：

  The syntheses of prosolanapyrones I (6) and II (7) via the aldol reactions of pyrone and dienal segments have been achieved in five steps in 31% overall yield for 6 and seven steps in 5% overall yield for 7. An improved synthetic route starting from vinylpyrone 27 provided 7 in 11 steps in 12% overall yield. The enzymatic Diels-Alder reaction of 7 affords (-)-solanapyrone A (1) with high enantioselectivity and with good exo-selectivity, which is difficult to attain by chemical methods. In addition, a crude enzyme preparation from Alternaria solani has been used to perform a kinetic resolution of(+/-)-3.

  DOI：

  10.1021/jo980743r

文献信息

• A new protocol for synthesis of 3-hydroxymethyl-4-methoxy-2 H -pyrone derivatives
  作者：Hisahiro Hagiwara、Katsuhiro Kobayashi、Takashi Hoshi、Toshio Suzuki、Masayoshi Ando

  DOI：10.1016/s0040-4020(01)00347-7

  日期：2001.6

  The title compounds have been prepared by treatment of 4-methoxy-3-phenylsulfinylmethyl-2H-pyrone derivatives with trifluoroacetic anhydride, followed by basic work-up. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Total Synthesis of (−)-Solanapyrone A via Enzymatic Diels−Alder Reaction of Prosolanapyrone
  作者：Hideaki Oikawa、Tomonori Kobayashi、Kinya Katayama、Yuichi Suzuki、Akitami Ichihara

  DOI：10.1021/jo980743r

  日期：1998.11.1

  The syntheses of prosolanapyrones I (6) and II (7) via the aldol reactions of pyrone and dienal segments have been achieved in five steps in 31% overall yield for 6 and seven steps in 5% overall yield for 7. An improved synthetic route starting from vinylpyrone 27 provided 7 in 11 steps in 12% overall yield. The enzymatic Diels-Alder reaction of 7 affords (-)-solanapyrone A (1) with high enantioselectivity and with good exo-selectivity, which is difficult to attain by chemical methods. In addition, a crude enzyme preparation from Alternaria solani has been used to perform a kinetic resolution of(+/-)-3.