(3aS,4R,5R,7aS)-7-bromo-4,5-dimethoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxole | 1572455-04-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4R,5R,7aS)-7-bromo-4,5-dimethoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxole
• CAS: 1572455-04-9
• 化学式: C₁₁H₁₇BrO₄
• 分子量: 293.158
• InChiKey: SEDGBUYSNZLJIP-ZYUZMQFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3aS,4R,5R,7aS)-7-bromo-4,5-dimethoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxole 在 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 (3aS,4R,5R,7aS)-7-bromo-4,5-dimethoxy-2-(4-methoxyphenyl)-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxole
  参考文献：
  名称：

  Chemoenzymatic Total Syntheses of Ribisins A, B, and D, Polyoxygenated Benzofuran Derivatives Displaying NGF-Potentiating Properties

  摘要：

  Total syntheses of the structures, 1, 2, and 4, assigned to the biologically active natural products ribisins A, B, and D, respectively, have been achieved using the microbially derived and enantiomerically pure cis-1,2-dihydrocatechol 5 as starting material. Key steps include Suzuki-Miyaura cross-coupling, intramolecular Mitsunobu, and tandem epoxidation/rearrangement reactions. As a result of these studies, the structures of ribisins A and D have been confirmed while that of congener B was shown to be represented by 31 rather than 2.

  DOI：

  10.1021/jo500210k
• 作为产物：
  描述：

  (3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 在 四氧化锇 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 丙酮 、 mineral oil 为溶剂， 反应 9.5h， 生成 (3aS,4R,5R,7aS)-7-bromo-4,5-dimethoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxole
  参考文献：
  名称：

  Chemoenzymatic Total Syntheses of Ribisins A, B, and D, Polyoxygenated Benzofuran Derivatives Displaying NGF-Potentiating Properties

  摘要：

  Total syntheses of the structures, 1, 2, and 4, assigned to the biologically active natural products ribisins A, B, and D, respectively, have been achieved using the microbially derived and enantiomerically pure cis-1,2-dihydrocatechol 5 as starting material. Key steps include Suzuki-Miyaura cross-coupling, intramolecular Mitsunobu, and tandem epoxidation/rearrangement reactions. As a result of these studies, the structures of ribisins A and D have been confirmed while that of congener B was shown to be represented by 31 rather than 2.

  DOI：

  10.1021/jo500210k