(2R,3R)-3,5-dimethyl-2-phenyl-2,3-dihydro-4H-pyran-4-one | 88198-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,3R)-3,5-dimethyl-2-phenyl-2,3-dihydro-4H-pyran-4-one
• 英文别名: 3,5-dimethyl-2-phenyl-2,3-dihydro-4H-pyran-4-one；(2R,3R)-3,5-dimethyl-2-phenyl-2,3-dihydropyran-4-one
• CAS: 88198-71-4
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: FHQSXHVXYDHRPI-GXFFZTMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3,5-dimethyl-2-phenyl-2,3-dihydro-4H-pyran-4-one 、 重氮甲烷 生成 methyl 3-hydroxy-2-methyl-3-phenylpropanoate
  参考文献：
  名称：

  BEDNARSKI, M.;MARING, C.;DANISHEFSKY, S., TETRAHEDRON LETT., 1983, 24, N 33, 3451-3454

  摘要：

  DOI：
• 作为产物：
  描述：

  [(2R,3R,6S)-6-methoxy-3,5-dimethyl-2-phenyl-3,6-dihydro-2H-pyran-4-yl]oxy-trimethylsilane 、 三氟乙酸 生成 (2R,3R)-3,5-dimethyl-2-phenyl-2,3-dihydro-4H-pyran-4-one
  参考文献：
  名称：

  BEDNARSKI, M.;MARING, C.;DANISHEFSKY, S., TETRAHEDRON LETT., 1983, 24, N 33, 3451-3454

  摘要：

  DOI：

文献信息

• Asymmetric hetero Diels-Alder reaction catalyzed by stable and easily prepared CAB catalysts
  作者：Qingzhi Gao、Kazuaki Ishihara、Tohru Maruyama、Makoto Mouri、Hisashi Yamamoto

  DOI：10.1016/s0040-4020(01)80812-7

  日期：1994.1

  A stable chiral (acyloxy)borane (CAB) complex is prepared in situ by mixing a tartaric acid derivative and arylboronic acids at room temperature. A solution of the catalyst is effective in catalyzing hetero Diels-Alder reactions to produce dihydropyrone derivatives of high optical purities.

  通过在室温下混合酒石酸衍生物和芳基硼​​酸原位制备稳定的手性（酰氧基）硼烷（CAB）配合物。该催化剂的溶液有效地催化杂Diels-Alder反应以产生高光学纯度的二氢吡喃酮衍生物。
• AnN,N′-Dioxide/In(OTf)3 Catalyst for the Asymmetric Hetero-Diels–Alder Reaction Between Danishefsky's Dienes and Aldehydes: Application in the Total Synthesis of Triketide
  作者：Zhipeng Yu、Xiaohua Liu、Zhenhua Dong、Mingsheng Xie、Xiaoming Feng

  DOI：10.1002/anie.200704759

  日期：2008.2.1
• Asymmetric hetero Diels-Alder reaction catalyzed by stable and easily prepared chiral (acyloxy)borane (CAB) catalysts
  作者：Qingzhi Gao、Tohru Maruyama、Makoto Mouri、Hisashi Yamamoto

  DOI：10.1021/jo00033a005

  日期：1992.3

  A stable chiral (acyloxy)borane (CAB) complex is prepared in situ by mixing tartaric acid derivative and arylboric acid at room temperature. A solution of the catalyst is effective to catalyze hetero Diels-Alder reaction to produce dihydropyrone derivatives of high optical purities.
• Asymmetric hetero-Diels-Alder reaction catalyzed by a chiral organoaluminum reagent
  作者：Keiji. Maruoka、Takayuki. Itoh、Tadashi. Shirasaka、Hisashi. Yamamoto

  DOI：10.1021/ja00209a061

  日期：1988.1
• Mild Lewis acid catalysis: tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium-mediated hetero-Diels-Alder reaction
  作者：M. Bednarski、S. Danishefsky

  DOI：10.1021/ja00349a064

  日期：1983.6