8-(3-acetyloxiran-2-yl)-7-methoxy-2H-chromen-2-one | 600173-56-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-(3-acetyloxiran-2-yl)-7-methoxy-2H-chromen-2-one
• 英文别名: 8-(3-Acetyloxiran-2-yl)-7-methoxychromen-2-one
• CAS: 600173-56-6
• 化学式: C₁₄H₁₂O₅
• 分子量: 260.246
• InChiKey: NOUMVRSPEUZAQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲基三苯基溴化膦 、 8-(3-acetyloxiran-2-yl)-7-methoxy-2H-chromen-2-one 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以28%的产率得到phebalosin
  参考文献：
  名称：

  A route to the structure proposed for puetuberosanol and approaches to the natural products marshrin and phebalosin

  摘要：

  Synthesis of the structure claimed for puetuberosanol 1 (using the Julia-Colonna oxidation in a key step) showed that the natural product was a different material. The isomeric epoxy alcohols 16-18 can be discounted from the alternatives. An analogue 19 of marshrin 2 was prepared but the synthesis of the natural product was thwarted by failure of a Julia-Colonna oxidation in the key step. The epoxy ketone 29 was prepared by Darzens condensation and was converted into (+/-)-phebalosin 3. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00624-0
• 作为产物：
  描述：

  8-iodo-7-methoxy-2H-chromen-2-one 在 异丙基氯化镁 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 30.0h， 生成 8-(3-acetyloxiran-2-yl)-7-methoxy-2H-chromen-2-one
  参考文献：
  名称：

  A route to the structure proposed for puetuberosanol and approaches to the natural products marshrin and phebalosin

  摘要：

  Synthesis of the structure claimed for puetuberosanol 1 (using the Julia-Colonna oxidation in a key step) showed that the natural product was a different material. The isomeric epoxy alcohols 16-18 can be discounted from the alternatives. An analogue 19 of marshrin 2 was prepared but the synthesis of the natural product was thwarted by failure of a Julia-Colonna oxidation in the key step. The epoxy ketone 29 was prepared by Darzens condensation and was converted into (+/-)-phebalosin 3. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00624-0

文献信息

• A route to the structure proposed for puetuberosanol and approaches to the natural products marshrin and phebalosin
  作者：Adam Gillmore、Christelle Lauret、Stanley M Roberts

  DOI：10.1016/s0040-4020(03)00624-0

  日期：2003.6

  Synthesis of the structure claimed for puetuberosanol 1 (using the Julia-Colonna oxidation in a key step) showed that the natural product was a different material. The isomeric epoxy alcohols 16-18 can be discounted from the alternatives. An analogue 19 of marshrin 2 was prepared but the synthesis of the natural product was thwarted by failure of a Julia-Colonna oxidation in the key step. The epoxy ketone 29 was prepared by Darzens condensation and was converted into (+/-)-phebalosin 3. (C) 2003 Elsevier Science Ltd. All rights reserved.