3,5,5-Trimethyl-6-phenyl-2,3,5,6-tetrahydropyran-2,4-dione | 329787-84-0

• 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: 3,5,5-Trimethyl-6-phenyl-2,3,5,6-tetrahydropyran-2,4-dione
• 英文别名: 6-phenyl-3,5,5-trimethyl-2,3,5,6-tetrahydropyran-2,4-dione；2H-Pyran-2,4(3H)-dione, dihydro-3,5,5-trimethyl-6-phenyl-；3,5,5-trimethyl-6-phenyloxane-2,4-dione
• CAS: 329787-84-0
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: UMJRKBNYWMJTJT-UHFFFAOYSA-N

物化性质

• 熔点：
  172-174 °C(Solv: chloroform (67-66-3))
• 沸点：
  395.8±42.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  3,5,5-Trimethyl-6-phenyl-2,3,5,6-tetrahydropyran-2,4-dione 在 sodium methylate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 生成 6-phenyl-4-(4-methylphenylsulfonyloxy)-3,5,5-trimethyl-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Reactions of Sodium Enolates Derived from 6-Aryl-3,5,5-trimethyl-2,3,5,6-tetrahydropyrane-2,4-diones with Substituted Benzenesulfonyl Chlorides and Arenediazonium Salts

  摘要：

  Sodium enolates derived from 6-aryl-3,5,5-trimethyl-2,3,5,6-tetrahydropyrane-2,4-diones react with substituted benzenesulfonyl chlorides to give the corresponding O-sulfonation products, 6-aryl-4-(4-R-phenylsulfonyloxy)-3,5,5-trimethyl-5,6-dihydropyrane-2-ones. Reactions of the title compounds with arenediazonium tetrafluoroborates afford 6-aryl-3-arylazo-3,5,5-trimethyl-2,3,5,6-tetrahydropyran-2,4-diones as mixtures of syn and anti isomers.

  DOI：

  10.1023/b:rugc.0000007652.81421.04
• 作为产物：
  描述：

  Ethyl 2,4-dimethyl-3-isobutyryloxypent-2-enoate 在 溴 、 mercury dichloride 、 锌 作用下， 以 四氯化碳 、 乙醚 、 乙酸乙酯 为溶剂， 反应 0.25h， 生成 3,5,5-Trimethyl-6-phenyl-2,3,5,6-tetrahydropyran-2,4-dione
  参考文献：
  名称：

  Shchepin; Sazhneva; Russkikh, Russian Journal of Organic Chemistry, 2000, vol. 36, # 6, p. 774 - 776

  摘要：

  DOI：

文献信息

• Synthesis, Structure, and Keto-Enol Tautomerism of 3-R1-5,5-R2,R2-6-R3-2,3,5,6-Tetrahydropyran-2,4-diones
  作者：V. V. Shchepin、M. I. Kodess、Yu. Kh. Sazhneva、N. Yu. Russkikh

  DOI：10.1007/s11176-005-0477-6

  日期：2005.10

  Ethyl esters of 2,4-dibromo-2-R1-4-R2-3-oxopentanoic and -hexanoic acids react with zinc and aliphatic or aromatic aldehydes under the conditions of the Reformatskii reaction to give 3-R1-5,5-R2, R2-6-R3-2,3,5,6-tetrahydropyran-2,4-diones, which are obtained in three forms: keto, enol with enolization of the keto group, and enol with enolization of the ester group. The keto form is isolated by crystallization

  2,4-二溴-2-R 1 -4-R 2 -3-氧戊酸和-己酸的乙酯在Reformatskii反应的条件下与锌和脂族或芳族醛反应生成3-R 1 -5， 5-R 2，R 2 -6-R 3 -2,3,5,6-四氢吡喃-2,4-二酮以三种形式获得：酮基，带有酮基的烯醇化烯醇和带有烯化的烯醇酯基团。通过结晶从CCl 4和石油醚的混合物中分离出酮形式。第一种烯醇形式，来自MeOH，EtOH和极性非质子溶剂；第二种烯醇形式，来自CHCl 3。第二种烯醇形式在DMSO中被氧化以形成在杂环的3-位上含有羟基的酮化合物。
• ——
  作者：V. V. Shchepin、Yu. Kh. Sazhneva、N. Yu. Russkikh、M. I. Vakhrin

  DOI：10.1023/a:1013443809999

  日期：——
• ——
  作者：V. V. Shchepin

  DOI：10.1023/a:1023793013708

  日期：——
• Reactions of Sodium Enolates Derived from 6-Aryl-3,5,5-trimethyl-2,3,5,6-tetrahydropyrane-2,4-diones with Substituted Benzenesulfonyl Chlorides and Arenediazonium Salts
  作者：V. V. Shchepin、Yu. Kh. Sazhneva、M. V. Bagara、N. Yu. Russkikh

  DOI：10.1023/b:rugc.0000007652.81421.04

  日期：2003.8

  Sodium enolates derived from 6-aryl-3,5,5-trimethyl-2,3,5,6-tetrahydropyrane-2,4-diones react with substituted benzenesulfonyl chlorides to give the corresponding O-sulfonation products, 6-aryl-4-(4-R-phenylsulfonyloxy)-3,5,5-trimethyl-5,6-dihydropyrane-2-ones. Reactions of the title compounds with arenediazonium tetrafluoroborates afford 6-aryl-3-arylazo-3,5,5-trimethyl-2,3,5,6-tetrahydropyran-2,4-diones as mixtures of syn and anti isomers.
• Shchepin; Sazhneva; Russkikh, Russian Journal of Organic Chemistry, 2000, vol. 36, # 6, p. 774 - 776
  作者：Shchepin、Sazhneva、Russkikh、Litvinov

  DOI：——

  日期：——