4,5-bis(prop-2-enoxy)-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene | 914300-21-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,5-bis(prop-2-enoxy)-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene
• CAS: 914300-21-3
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: FLEUJGMEYRMGJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4,5-bis(prop-2-enoxy)-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene 在 吗啉 、 四(三苯基膦)钯 、 dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) 、 锌 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 12.0h， 生成 3,4-dihydroxy-7,8-dimethoxy-6H-naphtho[1,2-b]benzo[d]pyran-6-one
  参考文献：
  名称：

  Nickel-Catalyzed Synthesis of Benzocoumarins:  Application to the Total Synthesis of Arnottin I

  摘要：

  The ring-opening addition of methyl 2,3-dimethoxy-6-iodobenzoate to oxabenzonorbornadienes followed by cyclization in the presence of NiBr2( dppe) and Zn metal powder in acetonitrile at 80 C to give the corresponding benzocoumarin derivatives is described. This methodology was then applied to the synthesis of natural product arnottin I, first isolated from Xanthoxylum arnottianum Maxim, using protecting group chemistry. After deprotection and subsequent ring closure, arnottin I was obtained in 21% overall yield after six steps starting from catechol.

  DOI：

  10.1021/jo061477h
• 作为产物：
  描述：

  4,5-二溴苯-1,2-二醇 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 15.0h， 生成 4,5-bis(prop-2-enoxy)-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene
  参考文献：
  名称：

  Nickel-Catalyzed Synthesis of Benzocoumarins:  Application to the Total Synthesis of Arnottin I

  摘要：

  The ring-opening addition of methyl 2,3-dimethoxy-6-iodobenzoate to oxabenzonorbornadienes followed by cyclization in the presence of NiBr2( dppe) and Zn metal powder in acetonitrile at 80 C to give the corresponding benzocoumarin derivatives is described. This methodology was then applied to the synthesis of natural product arnottin I, first isolated from Xanthoxylum arnottianum Maxim, using protecting group chemistry. After deprotection and subsequent ring closure, arnottin I was obtained in 21% overall yield after six steps starting from catechol.

  DOI：

  10.1021/jo061477h

文献信息

• Cobalt-Catalyzed Allylation of Heterobicyclic Alkenes: Ligand-Induced Divergent Reactivities
  作者：Yuan Huang、Chao Ma、Yi Xin Lee、Rui-Zhi Huang、Yu Zhao

  DOI：10.1002/anie.201506003

  日期：2015.11.9

  The allylation of heterobicyclic alkenes is presented for the first time. By using an inexpensive cobalt salt as the catalyst and easy‐to‐handle potassium allyltrifluoroborate as the reagent, an unprecedented formal hydroallylation of the bicyclic alkenes is realized in high efficiency. When a chiral cobalt/bis(phosphine) complex is used instead, the alternative ring‐opening products can be obtained

  首次提出了杂双环烯烃的烯丙基化。通过使用廉价的钴盐作为催化剂并使用易于处理的烯丙基三氟硼酸钾作为试剂，可以高效地实现前所未有的双环烯烃正式加氢水解反应。当使用手性钴/双（膦）配合物时，可以高收率和出色的对映选择性获得替代的开环产物。
• Nickel-Catalyzed Synthesis of Benzocoumarins:  Application to the Total Synthesis of Arnottin I
  作者：Sachin Madan、Chien-Hong Cheng

  DOI：10.1021/jo061477h

  日期：2006.10.1

  The ring-opening addition of methyl 2,3-dimethoxy-6-iodobenzoate to oxabenzonorbornadienes followed by cyclization in the presence of NiBr2( dppe) and Zn metal powder in acetonitrile at 80 C to give the corresponding benzocoumarin derivatives is described. This methodology was then applied to the synthesis of natural product arnottin I, first isolated from Xanthoxylum arnottianum Maxim, using protecting group chemistry. After deprotection and subsequent ring closure, arnottin I was obtained in 21% overall yield after six steps starting from catechol.