2,3-bis(bromomethyl)-6,11-dioxa-5,12-dihydrobenzo[e]benzo[1,2-e]cycloocytene | 243637-29-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-bis(bromomethyl)-6,11-dioxa-5,12-dihydrobenzo[e]benzo[1,2-e]cycloocytene
• 英文别名: 8,9-Bis(bromomethyl)-6,11-dihydrobenzo[c][1,6]benzodioxocine
• CAS: 243637-29-8
• 化学式: C₁₆H₁₄Br₂O₂
• 分子量: 398.094
• InChiKey: OLIPWYAQCAERQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-bis(bromomethyl)-6,11-dioxa-5,12-dihydrobenzo[e]benzo[1,2-e]cycloocytene 在 caesium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 6.0h， 生成 9,13,20,24-tetraoxa-9,10,12,13,20,21,23,24-octahydro-3',4'-naphtho-9',10'-phenanthro[e,e']benzo[1,2-a:4,5-a']dicyclooctene
  参考文献：
  名称：

  Structure of supramolecular complex of flexible molecular tweezers and planar guest in solution

  摘要：

  Flexible molecular receptors having three aromatic chromophores can bind electron deficient planar guests both in the crystalline state and in solution. The crystalline complex has a triple-decker type donor-acceptor-donor sandwich arrangement in which the guest located between the two terminal aromatic chromophores of the host. Two orientations of the guest, parallel and cross, with respect to the phenanthrene ring of the host were predicted by a molecular mechanics calculation. The former structure was found in the crystalline state. Although the latter was predicted to be less stable, the observed complexation induced shift of the guest supports this orientation in solution. When the terminal naphthalene ring of the host was changed to a benzene ring, the stoichiometry of the crystalline complex changed either to 1:2 or 2:1 depending on the guest. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00848-1
• 作为产物：
  描述：

  邻苯二酚 、 四溴甲苯 在 caesium carbonate 作用下， 以 丙酮 为溶剂， 以32%的产率得到2,3-bis(bromomethyl)-6,11-dioxa-5,12-dihydrobenzo[e]benzo[1,2-e]cycloocytene
  参考文献：
  名称：

  基于二恶英[2.2]邻环烷骨架的分子镊子

  摘要：

  具有三个芳香族发色团的柔性分子受体可以通过面对面和面对面的相互作用结合缺乏电子的π系统，例如TCNQ，PDA，TCNB。两个末端芳环的顺界面取向对于结合客体是有效的。

  DOI：

  10.1016/s0040-4039(99)01033-3

文献信息

• Molecular tweezers based on dioxa[2.2]orthocyclophane skeleton
  作者：Hirotaka Kurebayashi、Masaya Sakaguchi、Toshiya Okajima、Takeharu Haino、Shuji Usui、Yoshimasa Fukazawa

  DOI：10.1016/s0040-4039(99)01033-3

  日期：1999.7

  Flexible molecular receptors having three aromatic chromophores can bind electron-deficient π-system such as TCNQ, PDA, TCNB with both face-to-face and face-to-edge interactions. A syn cofacial orientation of the two terminal aromatic rings is effective for binding the guest.

  具有三个芳香族发色团的柔性分子受体可以通过面对面和面对面的相互作用结合缺乏电子的π系统，例如TCNQ，PDA，TCNB。两个末端芳环的顺界面取向对于结合客体是有效的。
• Structure of supramolecular complex of flexible molecular tweezers and planar guest in solution
  作者：Hirotaka Kurebayashi、Takeharu Haino、Shuji Usui、Yoshimasa Fukazawa

  DOI：10.1016/s0040-4020(01)00848-1

  日期：2001.10

  Flexible molecular receptors having three aromatic chromophores can bind electron deficient planar guests both in the crystalline state and in solution. The crystalline complex has a triple-decker type donor-acceptor-donor sandwich arrangement in which the guest located between the two terminal aromatic chromophores of the host. Two orientations of the guest, parallel and cross, with respect to the phenanthrene ring of the host were predicted by a molecular mechanics calculation. The former structure was found in the crystalline state. Although the latter was predicted to be less stable, the observed complexation induced shift of the guest supports this orientation in solution. When the terminal naphthalene ring of the host was changed to a benzene ring, the stoichiometry of the crystalline complex changed either to 1:2 or 2:1 depending on the guest. (C) 2001 Elsevier Science Ltd. All rights reserved.