(7E,13E)-(4R,9R,10S,16S)-4-Allyl-9-hydroxy-10,16-dimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione | 458564-72-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (7E,13E)-(4R,9R,10S,16S)-4-Allyl-9-hydroxy-10,16-dimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione
• 英文别名: (4R,7E,9R,10S,13E,16S)-9-hydroxy-10,16-dimethyl-4-prop-2-enyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione
• CAS: 458564-72-2
• 化学式: C₁₈H₂₄O₇
• 分子量: 352.384
• InChiKey: DWXVUEJTHMKRLP-ZUCDYZAFSA-N

物化性质

• 沸点：
  633.0±55.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (7E,13E)-(4R,9R,10S,16S)-4-Allyl-9-hydroxy-10,16-dimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione 在 palladium dichloride 氧气 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以72%的产率得到macrosphelide H
  参考文献：
  名称：

  Synthesis of macrosphelides H and G

  摘要：

  A compound with furyl and vinyl groups was designed as an intermediate for synthesis of macrosphelide H. The furyl group was oxidatively transformed into the key C(5)-O(10) part by a two-step conversion of (1) NBS, H2O: (2) NaClO2 without affecting the free hydroxyl group at C(3). thus furnishing the seco acid, while the Wacker oxidation at the final step was used to convert the vinyl group into acetyl group to afford macrosphelide H. This strategy was applied successfully to synthesis or macrosphelide G as well. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00781-5
• 作为产物：
  描述：

  (7E,13E)-(4R,10S,16S)-4-Allyl-10,16-dimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,9,12-tetraone 在 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 3,5-二硝基苯甲酸 、 三苯基膦 、 三乙胺 作用下， 以 甲醇 、 四氢呋喃 为溶剂， 以73%的产率得到(7E,13E)-(4R,9R,10S,16S)-4-Allyl-9-hydroxy-10,16-dimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione
  参考文献：
  名称：

  Synthesis of macrosphelides H and G

  摘要：

  A compound with furyl and vinyl groups was designed as an intermediate for synthesis of macrosphelide H. The furyl group was oxidatively transformed into the key C(5)-O(10) part by a two-step conversion of (1) NBS, H2O: (2) NaClO2 without affecting the free hydroxyl group at C(3). thus furnishing the seco acid, while the Wacker oxidation at the final step was used to convert the vinyl group into acetyl group to afford macrosphelide H. This strategy was applied successfully to synthesis or macrosphelide G as well. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00781-5