5-allyl-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one | 1021299-51-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 5-allyl-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
• 英文别名: 7-Methoxy-2,2-dimethyl-5-prop-2-enyl-1,3-benzodioxin-4-one
• CAS: 1021299-51-3
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: UZHSNSITRQQTKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-allyl-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 在 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以91%的产率得到2-(7-methoxy-2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)acetaldehyde
  参考文献：
  名称：

  Total Synthesis of 7-Deoxy-6-O-methylfusarentin Featuring a Chelation-Controlled 1,3-Reetz–Keck-Type Allylation

  摘要：

  The total synthesis of 7-deoxy-6-O-methylfiisarentin (1) and a formal synthesis of 7-deoxy-6,8-O-dimethylfusarentin (2) has been successfully achieved in 10 steps. The described tactic underscores a diastereoselective strategy which incorporates a single acyclic reaction based on the initial stereocenter by means of a 1,3-chelation-controlled Reetz-Keck-type allylation.

  DOI：

  10.1021/jo301167a
• 作为产物：
  描述：

  5-hydroxy-7-methoxy-2,2-dimethyl-benzo[1,3]dioxin-4-one 在 吡啶 、 四(三苯基膦)钯 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 48.5h， 生成 5-allyl-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
  参考文献：
  名称：

  Total Synthesis of 7-Deoxy-6-O-methylfusarentin Featuring a Chelation-Controlled 1,3-Reetz–Keck-Type Allylation

  摘要：

  The total synthesis of 7-deoxy-6-O-methylfiisarentin (1) and a formal synthesis of 7-deoxy-6,8-O-dimethylfusarentin (2) has been successfully achieved in 10 steps. The described tactic underscores a diastereoselective strategy which incorporates a single acyclic reaction based on the initial stereocenter by means of a 1,3-chelation-controlled Reetz-Keck-type allylation.

  DOI：

  10.1021/jo301167a

文献信息

• Total Synthesis of Cruentaren B
  作者：Tushar Kanti Chakraborty、Amit Kumar Chattopadhyay

  DOI：10.1021/jo800181n

  日期：2008.5.1

  A convergent total synthesis of the cytotoxic natural product cruentaren B is completed in 26 steps (longest linear sequence) with an overall yield of 7.1%. For the construction of the C1−C11 benzolactone fragment of the molecule, the key steps used were O-methylation, using a Mitsunobu reaction, a Stille coupling method to construct the C7−C8 bond, and a Brown’s asymmetric crotylboration reaction

  以26个步骤（最长的线性序列）完成细胞毒性天然产物crentaren B的会聚全合成，总收率为7.1％。对于分子的C 1 -C 11苯甲内酯片段的构建，使用的关键步骤是使用Mitsunobu反应的O-甲基化，构造C 7 -C 8键的Stille偶联方法和Brown不对称巴豆基硼酸酯化反应用于该片段中存在的两个手性中心的直接对映选择性安装。为了在C 12 -C 20聚酮化合物片段中进行手性中心的非对映选择性安装，应使用Evans syn在衍生自（R）-3-羟基-2-甲基丙酸甲酯的手性醛上进行醇醛醇醛缩醛反应，随后进行Mukaiyama醇醛醇醛缩合反应。为了构建C 21 -C 28尾巴，使用“非-Evans”顺式羟醛反应。通过S N 2反应和Wittig烯烃化反应，然后通过标准官能团操作将三个片段偶联，以提供目标分子。
• Total Synthesis of 7-Deoxy-6-<i>O</i>-methylfusarentin Featuring a Chelation-Controlled 1,3-Reetz–Keck-Type Allylation
  作者：Timothy N. Trotter、Aymara M. M. Albury、Michael P. Jennings

  DOI：10.1021/jo301167a

  日期：2012.9.7

  The total synthesis of 7-deoxy-6-O-methylfiisarentin (1) and a formal synthesis of 7-deoxy-6,8-O-dimethylfusarentin (2) has been successfully achieved in 10 steps. The described tactic underscores a diastereoselective strategy which incorporates a single acyclic reaction based on the initial stereocenter by means of a 1,3-chelation-controlled Reetz-Keck-type allylation.