endo-1,4-dibromotricyclo[5.2.1.0^2,6]deca-3,8-diene-5,10-dione 10-ethylene acetal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: endo-1,4-dibromotricyclo[5.2.1.0^2,6]deca-3,8-diene-5,10-dione 10-ethylene acetal
• 英文别名: (1'S,2'R,6'S,7'S)-4',7'-dibromospiro[1,3-dioxolane-2,10'-tricyclo[5.2.1.02,6]deca-4,8-diene]-3'-one
• 化学式: C₁₂H₁₀Br₂O₃
• 分子量: 362.018
• InChiKey: CWLJXBQYHGTEDC-QJSROADHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  endo-1,4-dibromotricyclo[5.2.1.0^2,6]deca-3,8-diene-5,10-dione 10-ethylene acetal 在 氯化亚砜 、 溴 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (+/-)-(3'α,3'aα,4'β,7'α,7'aα)-2',2',4'-tribromo-3'-chloro-2',3',3'a,4',7',7'a-hexahydrospiro(1,3-dioxolan-2,8'-[4,7]methano[1H]inden)-1'-one
  参考文献：
  名称：

  Indirect Monobromination of the Cubane Nucleus. The Synthesis of Dimethyl 2-Bromocubane- 1,4-dicarboxylate

  摘要：

  2-bromocubane-1,4-dicarboxylate (3) 的制备方法如下 的制备方法。 (3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione 8- 乙烯缩酮 (4)。

  DOI：

  10.1071/c98028
• 作为产物：
  描述：

  endo-2,4-dibromodicyclopentadiene-1,8-dione 1,8-bis(ethylene acetal) 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以91 %的产率得到endo-1,4-dibromotricyclo[5.2.1.0^2,6]deca-3,8-diene-5,10-dione 10-ethylene acetal
  参考文献：
  名称：

  1,3-二取代立方烷衍生物的实用合成

  摘要：

  报道了 1,3-二取代立方烷的稳健多克级合成（以前仅适用于毫克级）。该方法利用了一种容易获得的烯酮中间体，该中间体以前用于合成 1,4-二取代的立方烷，通过引入一种新颖的 Wharton 转置来获得有用数量的 1,3-二取代的立方烷，以用于各种应用。

  DOI：

  10.1039/d3cc02164e

文献信息

• Synthesis of Linear Tetraquinanes by [3+2] Cycloaddition, Chemoselective Allylation of 7-Ketonorbornene, and Ring-Rearrangement Metathesis as Key Steps
  作者：Sambasivarao Kotha、Arpit Agrawal

  DOI：10.1055/s-0042-1751365

  日期：——

  A nine-step synthetic sequence to linear tetraquinanes involving [3+2] cycloaddition, chemoselective allylation, and ring-rearrangement metathesis as key steps is reported. A chemoselective allylation of 7-ketonorbornene was realized for the first time by using indium powder and allyl bromide. By this method, norbornene ketones can be selectively allylated in the presence of a cyclopentanone moiety

  报道了线性四醌的九步合成序列，其中包括 [3+2] 环加成、化学选择性烯丙基化和环重排复分解作为关键步骤。利用铟粉和烯丙基溴首次实现了7-酮降冰片烯的化学选择性烯丙基化反应。通过这种方法，降冰片烯酮可以在环戊酮部分的存在下选择性地烯丙基化，从而得到良好收率的单烯丙基化 Barbier 型产物。
• A practical synthesis of 1,3-disubstituted cubane derivatives
  作者：Nahin Kazi、Marine C. Aublette、Sarah L. Allinson、Susannah C. Coote

  DOI：10.1039/d3cc02164e

  日期：——

  A robust multigram-scale synthesis of 1,3-disubstituted cubanes (previously only available on milligram-scale) is reported. The approach exploits a readily available enone intermediate previously used for the synthesis of 1,4-disubstituted cubanes, by introducing a novel Wharton transposition to access useful quantities of 1,3-disubstituted cubanes for diverse applications.

  报道了 1,3-二取代立方烷的稳健多克级合成（以前仅适用于毫克级）。该方法利用了一种容易获得的烯酮中间体，该中间体以前用于合成 1,4-二取代的立方烷，通过引入一种新颖的 Wharton 转置来获得有用数量的 1,3-二取代的立方烷，以用于各种应用。
• Synthesis of annulated oxa-triquinanes and oxa-diquinanes via cascade Michael addition-intramolecular alkylation involving α-halodicyclopentadienones
  作者：Sohan Lal、Arindrajit Chowdhury、Irishi N.N. Namboothiri

  DOI：10.1016/j.tet.2017.01.003

  日期：2017.3

  Base Mediated Michael addition of 1,3-dicarbonyl compounds to alpha-halodicyclopentadienones followed by cyclization of the intermediate Michael adducts leads to novel annulated dihydrofurans as single diastereomers. Such fused dihydrofurans, which are also oxa-triquinanes and oxa-diquinanes, undergo retro-Diels-Alder reaction to give cyclopentadiene-eliminated products in excellent yield. Certain 1,3dicarbonyl compounds exhibited a different reactivity profile with a-halodicyclopentadienones leading to spiro-cyclopropanes fused to dicyclopentadiene skeleton. (C) 2017 Elsevier Ltd. All rights reserved.
• Cubane derivatives 1. Synthesis and molecular structures of the esters of 1,4-cubanedicarboxylic acid
  作者：L. T. Eremenko、L. B. Romanova、M. E. Ivanova、I. L. Eremenko、S. E. Nefedov、Yu. T. Struchkov

  DOI：10.1007/bf00699835

  日期：1994.4

  An effective method of esterification of 1,4-cubanedicarboxylic acid with alkylsulfuric acids is proposed. The derivatives of alkanols with substantially different pK(a) values are obtained in high yields. Molecular structures of the esters obtained are confirmed by various methods. The X-ray study showed a remarkable effect of the nature of an alkyl radical on the geometry of the cubane core.
• Lowe, David A.; Moorhouse, Christopher J.; Walter, Justine M., Australian Journal of Chemistry, 1994, vol. 47, # 8, p. 1647 - 1650
  作者：Lowe, David A.、Moorhouse, Christopher J.、Walter, Justine M.、Tsanaktsidis, John

  DOI：——

  日期：——