(R)-6-((1E,3Z,7E,9E)-(5R,11R,12R,13S)-3-Ethyl-12-hydroxy-5,9,11,13-tetramethyl-pentadeca-1,3,7,9-tetraenyl)-5,6-dihydro-pyran-2-one | 331814-77-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-6-((1E,3Z,7E,9E)-(5R,11R,12R,13S)-3-Ethyl-12-hydroxy-5,9,11,13-tetramethyl-pentadeca-1,3,7,9-tetraenyl)-5,6-dihydro-pyran-2-one
• CAS: 331814-77-8
• 化学式: C₂₆H₄₀O₃
• 分子量: 400.602
• InChiKey: MERHIQOXROQICN-KBUYHITOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  29.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-6-((1E,3Z,7E,9E)-(5R,11R,12R,13S)-3-Ethyl-12-hydroxy-5,9,11,13-tetramethyl-pentadeca-1,3,7,9-tetraenyl)-5,6-dihydro-pyran-2-one 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以97%的产率得到(R)-6-((1E,3Z,7E,9E)-(5R,11R,13S)-3-Ethyl-5,9,11,13-tetramethyl-12-oxo-pentadeca-1,3,7,9-tetraenyl)-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  Participation of the β-hydroxyketone part for potent cytotoxicity of callystatin A, a spongean polyketide

  摘要：

  The participation of the beta -hydroxyketone part of callystatin A in the potent cytotoxicity was analyzed through the analogue-syntheses and the assessment of their biological potencies. The ketonic carbonyl, the 19-hydroxyl, and the three asymmetric methyl groups located in the beta -hydroxyketone part of callystatin A were revealed to contribute to the cytotoxic potency, respectively. Moreover, the alpha,beta -unsaturated delta -lactone portion was shown to serve as a conclusive functional group for the cytotoxic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00220-0
• 作为产物：
  描述：

  (2S,3R,4S)-3-[(tert-butyl)dimethylsilyloxy]-2,4-dimethylhexanal 在 2,6-二甲基吡啶 、 正丁基锂 、 四溴化碳 、 二异丁基氢化铝 、 氟化氢吡啶 、 二甲基亚砜 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 97.42h， 生成 (R)-6-((1E,3Z,7E,9E)-(5R,11R,12R,13S)-3-Ethyl-12-hydroxy-5,9,11,13-tetramethyl-pentadeca-1,3,7,9-tetraenyl)-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  Participation of the β-hydroxyketone part for potent cytotoxicity of callystatin A, a spongean polyketide

  摘要：

  The participation of the beta -hydroxyketone part of callystatin A in the potent cytotoxicity was analyzed through the analogue-syntheses and the assessment of their biological potencies. The ketonic carbonyl, the 19-hydroxyl, and the three asymmetric methyl groups located in the beta -hydroxyketone part of callystatin A were revealed to contribute to the cytotoxic potency, respectively. Moreover, the alpha,beta -unsaturated delta -lactone portion was shown to serve as a conclusive functional group for the cytotoxic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00220-0