(S)-5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one | 132604-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one
• 英文别名: (S)-6-methyl-3,5,6-trihydro-2H-pyran-2,4-dione；6-methyldihydropyran-2,4-dione；(S)-6-methyldihydro-2H-pyran-2,4(3H)-dione；(6S)-6-methyloxane-2,4-dione
• CAS: 132604-11-6
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: UUVIHKCBKAOTEW-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one 在 palladium on activated charcoal 、 镍 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 苯 为溶剂， 生成 (S)-5-己内酯
  参考文献：
  名称：

  发酵面包酵母高度对映体选择性还原乙酰乙酰化me酸

  摘要：

  用发酵的酵母将对乙酰乙酰化的麦德鲁姆酸进行对映体选择性还原，得到相应的手性（S）-醇，可以很容易地将其转化为δ-内酯衍生物。

  DOI：

  10.1016/s0040-4039(00)88516-0
• 作为产物：
  描述：

  isopropilydene (1-hydroxy-3-oxo-butylidene) malonate 在 蔗糖 作用下， 以 水 、 苯 为溶剂， 反应 12.0h， 生成 (S)-5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one
  参考文献：
  名称：

  发酵面包酵母高度对映体选择性还原乙酰乙酰化me酸

  摘要：

  用发酵的酵母将对乙酰乙酰化的麦德鲁姆酸进行对映体选择性还原，得到相应的手性（S）-醇，可以很容易地将其转化为δ-内酯衍生物。

  DOI：

  10.1016/s0040-4039(00)88516-0

文献信息

• Tabuchi, Hiroyasu; Ichihara, Akitami, Journal of the Chemical Society. Perkin transactions I, 1994, # 1, p. 125 - 134
  作者：Tabuchi, Hiroyasu、Ichihara, Akitami

  DOI：——

  日期：——
• Total Synthesis of (R)- and (S)-semi-Vioxanthin
  作者：Daniel Drochner、Michael Müller

  DOI：10.1002/1099-0690(200101)2001:1<211::aid-ejoc211>3.3.co;2-i

  日期：2001.1
• Total Synthesis of Acaulide and Acaulone A
  作者：Jun Hirabayashi、Fumika Yakushiji、Akira Katsuyama、Satoshi Ichikawa

  DOI：10.1021/acs.orglett.0c01907

  日期：2020.7.17

  Acaulide and acaulone A, which contain 14-membered macrodiolides, were isolated from a culture of Acaulium sp. H-JQSF. The antiosteoporosis activity of acaulide is expected to contribute to drug discovery research for an aging society. We herein report the first total synthesis of acaulide, acaulone A, and 10-keto-acaudiol A. Acaulide and acaulone A were synthesized via the late stage Michael addition to the 14-membered macrodiolide, which was inspired by plausible biosynthetic pathways. This approach succeeded in the construction of the acaulide skeleton, which revealed the specific conformation of the 14-membered macrodiolide for late stage functionalization.
• The cycloaddition way to novel deoxy disaccharide analogs
  作者：Maria M. Tamarez、Richard W. Franck、Aloma Geer

  DOI：10.1016/s0040-4020(03)00654-9

  日期：2003.6

  A novel heterocycloaddition merges 2-thiono-3-ketolactones with carbohydrate glycals to afford materials which resemble disaccharides with an O-glycosidic linkage at the anomeric center and a thioether linking both C-2 and C-2', thus creating a third heterocyclic ring. Upon desulfurization, these novel cycloadducts afford materials which are models for 2-deoxydisaccharides. Studies with two keto lactones and seven glycals are described. (C) 2003 Elsevier Science Ltd. All rights reserved.
• SATO, MASAYUKI;SAKAKI, JUN-ICHI;SUGITA, YOSHIAKI;NAKANO, TSUYOSHI;KANEKO,+, TETRAHEDRON LETT., 31,(1990) N1, C. 7463-7466
  作者：SATO, MASAYUKI、SAKAKI, JUN-ICHI、SUGITA, YOSHIAKI、NAKANO, TSUYOSHI、KANEKO,+

  DOI：——

  日期：——