2-(4-benzyloxy-3-methoxyphenyl)-5-(3-benzyloxypropyl)-7-methoxybenzofuran-3-carbaldehyde | 1124172-46-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(4-benzyloxy-3-methoxyphenyl)-5-(3-benzyloxypropyl)-7-methoxybenzofuran-3-carbaldehyde
• 英文别名: 7-Methoxy-2-(3-methoxy-4-phenylmethoxyphenyl)-5-(3-phenylmethoxypropyl)-1-benzofuran-3-carbaldehyde
• CAS: 1124172-46-8
• 化学式: C₃₄H₃₂O₆
• 分子量: 536.624
• InChiKey: MPOQUOFTTUKUQG-UHFFFAOYSA-N

物化性质

• 熔点：
  70-72 °C
• 沸点：
  690.1±55.0 °C(predicted)
• 密度：
  1.195±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-benzyloxy-3-methoxyphenyl)-5-(3-benzyloxypropyl)-7-methoxybenzofuran-3-carbaldehyde 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)-3-benzo[b]furan-carbaldehyde
  参考文献：
  名称：

  Facile Total Synthesis of Benzo[b]furan Natural Product XH-14

  摘要：

  An efficient and practical total synthesis of benzo[b]furan natural product XH-14 is demonstrated in nine steps from vanillin. Introduction of iodide substituents in the reaction including optimization of the reaction sequences is essential for the successful synthesis of XH-14. Sonogashira coupling with iodobenzene, iodine-induced cyclization, Wittig reaction, and formylation are critical in the high-yield total synthesis of XH-14.

  DOI：

  10.1080/00397910802399924
• 作为产物：
  描述：

  哌啶-1-甲醛 、 2-(4-benzyloxy-3-methoxyphenyl)-3-iodo-5-(3-benzyloxypropyl)-7-methoxybenzofuran 在 正丁基锂 、 盐酸 作用下， 以 正己烷 、 甲苯 、 水 为溶剂， 反应 0.5h， 以70%的产率得到2-(4-benzyloxy-3-methoxyphenyl)-5-(3-benzyloxypropyl)-7-methoxybenzofuran-3-carbaldehyde
  参考文献：
  名称：

  Facile Total Synthesis of Benzo[b]furan Natural Product XH-14

  摘要：

  An efficient and practical total synthesis of benzo[b]furan natural product XH-14 is demonstrated in nine steps from vanillin. Introduction of iodide substituents in the reaction including optimization of the reaction sequences is essential for the successful synthesis of XH-14. Sonogashira coupling with iodobenzene, iodine-induced cyclization, Wittig reaction, and formylation are critical in the high-yield total synthesis of XH-14.

  DOI：

  10.1080/00397910802399924

文献信息

• Facile Total Synthesis of Benzo[<i>b</i>]furan Natural Product XH-14
  作者：Hyun Bae Bang、Su Young Han、Da Hye Choi、Deok Mo Yang、Jung Woon Hwang、Hyun Suck Lee、Jong-Gab Jun

  DOI：10.1080/00397910802399924

  日期：2009.1.13

  An efficient and practical total synthesis of benzo[b]furan natural product XH-14 is demonstrated in nine steps from vanillin. Introduction of iodide substituents in the reaction including optimization of the reaction sequences is essential for the successful synthesis of XH-14. Sonogashira coupling with iodobenzene, iodine-induced cyclization, Wittig reaction, and formylation are critical in the high-yield total synthesis of XH-14.