4-methoxy-6-methyl-3-[(thiophenyl)methyl]-2H-pyran-2-one | 218435-72-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-methoxy-6-methyl-3-[(thiophenyl)methyl]-2H-pyran-2-one
• 英文别名: 4-methoxy-6-methyl-3-phenylthiomethyl-2H-pyran-2-one；4-Methoxy-6-methyl-3-(phenylsulfanylmethyl)pyran-2-one；4-methoxy-6-methyl-3-(phenylsulfanylmethyl)pyran-2-one
• CAS: 218435-72-4
• 化学式: C₁₄H₁₄O₃S
• 分子量: 262.329
• InChiKey: HKXBLFBSKWEZQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-6-methyl-3-[(thiophenyl)methyl]-2H-pyran-2-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%的产率得到4-methoxy-6-methyl-3-[(phenylsulfoxy)methyl]-2H-pyran-2-one
  参考文献：
  名称：

  Substrate Diversity of Macrophomate Synthase Catalyzing an Unusual Multistep Transformation from 2-Pyrones to Benzoates

  摘要：

  我们最近纯化了一种名为黑腐醇合酶的酶，它催化一种不寻常的多步转化过程，从5-乙酰基-4-甲氧基-6-甲基-2-吡営转变为4-乙酰基-3-甲氧基-5-甲基苯甲酸（黑腐酸）。为了研究该酶的底物多样性，我们制备了40种2-吡喃酮的类似物，并考察了它们在酶促转化中的相对效率。实验结果揭示了底物的结构要求和酶活性位点的大致尺寸，并消除了全细胞实验中因其他酶污染导致的模糊性。

  DOI：

  10.1271/bbb.64.530
• 作为产物：
  描述：

  苯硫酚 在 哌啶 、 聚合甲醛 、 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 4.0h， 生成 4-methoxy-6-methyl-3-[(thiophenyl)methyl]-2H-pyran-2-one
  参考文献：
  名称：

  A new protocol for synthesis of 3-hydroxymethyl-4-methoxy-2 H -pyrone derivatives

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)00347-7

文献信息

• 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.
• Substrate Diversity of Macrophomate Synthase Catalyzing an Unusual Multistep Transformation from 2-Pyrones to Benzoates
  作者：Kenji WATANABE、Takashi MIE、Akitami ICHIHARA、Hideaki OIKAWA、Mamoru HONMA

  DOI：10.1271/bbb.64.530

  日期：2000.1

  Macrophomate synthase, which we have recently purified, catalyzes an unusual multistep transformation from 5-acetyl-4-methoxy-6-methyl-2-pyrone to 4-acetyl-3-methoxy-5-methyl-benzoic acid (macrophomic acid). To investigate the substrate diversity of the enzyme, 40 analogs of 2-pyrone were prepared and their relative efficiency was examined in the enzymatic conversions. The experimental results reveal the structural requirements of the substrates and the rough size of the enzyme active site, and eliminate the ambiguity caused by contamination by other enzymes in the whole-cell experiments.

  我们最近纯化了一种名为黑腐醇合酶的酶，它催化一种不寻常的多步转化过程，从5-乙酰基-4-甲氧基-6-甲基-2-吡営转变为4-乙酰基-3-甲氧基-5-甲基苯甲酸（黑腐酸）。为了研究该酶的底物多样性，我们制备了40种2-吡喃酮的类似物，并考察了它们在酶促转化中的相对效率。实验结果揭示了底物的结构要求和酶活性位点的大致尺寸，并消除了全细胞实验中因其他酶污染导致的模糊性。
• 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.