(6R)-dihydro-6-methyl-2H-pyran-2,4(3H)-dione | 148586-29-2

• 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: (6R)-dihydro-6-methyl-2H-pyran-2,4(3H)-dione
• 英文别名: β-keto-δ-valerolactone；(R)-5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one；(R)-6-methyldihydro-2H-pyran-2,4(3H)-dione；(6R)-6-methyloxane-2,4-dione
• CAS: 148586-29-2
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: UUVIHKCBKAOTEW-SCSAIBSYSA-N

物化性质

• 沸点：
  296.1±33.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

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：

  (6R)-dihydro-6-methyl-2H-pyran-2,4(3H)-dione 在 4-二甲氨基吡啶 、 lithium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 25.0~120.0 ℃ 、101.33 kPa 条件下， 反应 37.83h， 生成 alternaric acid
  参考文献：
  名称：

  Total Synthesis and Stereochemistry of Alternaric Acid

  摘要：

  Determination of the stereochemistry and the total synthesis of alternaric acid 1 has been achieved. The stereostructure of 1 has been elucidated by stereoselective synthesis of four diastereoisomers of the C(9)-C(14) fragment 6, which had been obtained as a degradation product during structural studies. Key reactions of the total synthesis of 1 include the Julia olefination of tertiary aldehyde 6 and phenylsulfone 7 and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydro-2-pyrone via Fries-type rearrangement of the O-enol acyl group of beta-keto-delta-valerolactone toward the a-position of the delta-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1. The modified Fries-type rearrangement method has also been extended to the synthesis of some other compounds containing a tricarbonylmethane structure.

  DOI：

  10.1021/jo00096a016
• 作为产物：
  描述：

  己酸,5-羟基-3-羰基-,1,1-二甲基乙基酯,(S)- 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (6R)-dihydro-6-methyl-2H-pyran-2,4(3H)-dione
  参考文献：
  名称：

  萘螺酮A的不对称全合成

  摘要：

  首次合成了具有细胞毒性和抗菌作用的天然产物萘螺酮A。构建其螺[双环[3.2.1]辛烷-吡喃]核的关键是一个两步序列，涉及氢解脱溴烯烃迁移，然后是碱诱导的分子内羟醛型环化。

  DOI：

  10.1002/anie.202303229

文献信息

• Total synthesis of alternaric acid
  作者：Hiroyasu Tabuchi、Taisuke Hamamoto、Shokyo Miki、Tsuyoshi Tejima、Akitami Ichihara

  DOI：10.1016/s0040-4039(00)77605-2

  日期：1993.4

  A total synthesis of alternaric acid (1) has been achieved. Key reactions include the Julia olefination of tertiary aldehyde 4 and phenylsulfone 5, and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydropyrone via Fries type rearrangement of O-enolacyl group of beta-keto-delta-valerolactone toward alpha-position of the delta-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1.
• 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
• Tabuchi, Hiroyasu; Oikawa, Hideaki; Ichihara, Akitami, Journal of the Chemical Society. Perkin transactions I, 1994, # 19, p. 2833 - 2840
  作者：Tabuchi, Hiroyasu、Oikawa, Hideaki、Ichihara, Akitami

  DOI：——

  日期：——
• Total Synthesis and Stereochemistry of Alternaric Acid
  作者：Hiroyasu Tabuchi、Taisuke Hamamoto、Shokyo Miki、Tsuyoshi Tejima、Akitami Ichihara

  DOI：10.1021/jo00096a016

  日期：1994.8

  Determination of the stereochemistry and the total synthesis of alternaric acid 1 has been achieved. The stereostructure of 1 has been elucidated by stereoselective synthesis of four diastereoisomers of the C(9)-C(14) fragment 6, which had been obtained as a degradation product during structural studies. Key reactions of the total synthesis of 1 include the Julia olefination of tertiary aldehyde 6 and phenylsulfone 7 and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydro-2-pyrone via Fries-type rearrangement of the O-enol acyl group of beta-keto-delta-valerolactone toward the a-position of the delta-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1. The modified Fries-type rearrangement method has also been extended to the synthesis of some other compounds containing a tricarbonylmethane structure.