(nona-2,7-diyne-5,5-diyldisulfonyl)dibenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (nona-2,7-diyne-5,5-diyldisulfonyl)dibenzene
• 英文别名: 5,5-bis(phenylsulfonyl)nona-2,7-diyne；5-(Benzenesulfonyl)nona-2,7-diyn-5-ylsulfonylbenzene
• 化学式: C₂₁H₂₀O₄S₂
• 分子量: 400.519
• InChiKey: QDNTXLMLZYMWLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (nona-2,7-diyne-5,5-diyldisulfonyl)dibenzene 、 噁唑-2-酮 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以100%的产率得到4,7-dimethyl-2,2-bis(phenylsulfonyl)-2,3-dihydro-1H-inden-5-amine
  参考文献：
  名称：

  Rhodium-Catalyzed Decarboxylative Cycloaddition Route to Substituted Anilines

  摘要：

  A convenient method for preparing substituted anilines via a Rh-catalyzed [2 + 2 + 2] cycloaddition reaction of diynes and 2-oxazolone was discovered. The initial cycloaddition adducts undergo facile decarboxylation of carbon dioxide to afford aniline products. Reaction conditions are mild, and only 3 mol % Rh catalyst is required. High regioselectivity was observed when an unsymmetrical diyne was used as a starting material.

  DOI：

  10.1021/jo200236h
• 作为产物：
  描述：

  双苯磺酸甲烷 、 1-溴-2-丁炔 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 40.5h， 以49%的产率得到(nona-2,7-diyne-5,5-diyldisulfonyl)dibenzene
  参考文献：
  名称：

  Rhodium-Catalyzed Decarboxylative Cycloaddition Route to Substituted Anilines

  摘要：

  A convenient method for preparing substituted anilines via a Rh-catalyzed [2 + 2 + 2] cycloaddition reaction of diynes and 2-oxazolone was discovered. The initial cycloaddition adducts undergo facile decarboxylation of carbon dioxide to afford aniline products. Reaction conditions are mild, and only 3 mol % Rh catalyst is required. High regioselectivity was observed when an unsymmetrical diyne was used as a starting material.

  DOI：

  10.1021/jo200236h

文献信息

• An Expeditious Route to Eight‐Membered Heterocycles By Nickel‐Catalyzed Cycloaddition: Low‐Temperature CC Bond Cleavage
  作者：Puneet Kumar、Kainan Zhang、Janis Louie

  DOI：10.1002/anie.201203521

  日期：2012.8.20

  diynes undergo a cycloaddition reaction catalyzed by Ni/IPr to give dihydroazocine compounds (see scheme; IPr=1,3‐bis(2,6‐diisopropylphenyl)imidazolidene). The reaction involves a challenging CC bond cleavage step, yet, surprisingly, proceeds at low temperature.

  冷静的休息：3-氮杂环丁酮和各种二炔在 Ni/IPr 催化下发生环加成反应，得到二氢氮杂辛化合物（参见方案；IPr=1,3-双（2,6-二异丙基苯基）咪唑烷）。该反应涉及具有挑战性的C - C键断裂步骤，但令人惊讶的是，该反应在低温下进行。
• Rhodium-Catalyzed [2+2+2] Cyclo­addition-Aromatization of 1,6-Di­ynes with Cyclic Enol Ethers at Room Temperature
  作者：Yukimasa Aida、Shino Tooriyama、Yuki Kimura、Hiromi Hara、Yu Shibata、Ken Tanaka

  DOI：10.1002/ejoc.201501282

  日期：2016.1

  A cationic rhodium(I)/BINAP [2,2′-bis(diphenylphosphino)-1,1′-binaphthyl] complex is capable of catalyzing the [2+2+2] cycloaddition–aromatization of 1,6-diynes with cyclic enol ethers (2,3-dihydrofuran and dihydropyran) at room temperature to produce the corresponding aryl alkanol derivatives in good yields. In this process, a conjugated dihydrofuran showed a significantly higher reactivity than a

  阳离子铑(I)/BINAP [2,2'-双(二苯基膦)-1,1'-联萘]复合物能够催化1,6-二炔的[2+2+2]环加成-芳构化烯醇醚（2,3-二氢呋喃和二氢吡喃）在室温下以良好的产率制备相应的芳基烷醇衍生物。在这个过程中，共轭二氢呋喃比非共轭二氢呋喃表现出明显更高的反应性。
• On the Mechanism of the Puzzling “Endocyclic” Skeletal Rearrangement of 1,6-Enynes
  作者：Noemí Cabello、Eloísa Jiménez-Núñez、Elena Buñuel、Diego J. Cárdenas、Antonio M. Echavarren

  DOI：10.1002/ejoc.200700402

  日期：2007.9

  presence of gold(I) catalysts, whereas increasing electron-withdrawing character of substituents at C-4 leads to five-membered rings. Reactions of these simple enynes in the presence of PtCl4 as catalyst give exclusively exo-double skeletal rearrangements. Enynes substituted at the alkyne also react with AuI catalysts to give exclusively products of exo-double rearrangement. The different mechanisms

  已经研究了简单 1,6-烯炔的骨架重排，以确定控制五元或六元环形成的因素。在金 (I) 催化剂存在下，仅在 C-4 处取代的简单 1,6-烯炔优先产生六元环，而在 C-4 处增加取代基的吸电子特性导致五元环。在 PtCl4 作为催化剂存在下，这些简单的烯炔反应仅产生外双骨架重排。在炔烃上被取代的炔烃也与 AuI 催化剂反应，得到专门的外双重排产物。通过 DFT 计算分析了不同的机制。虽然发现了形成六元环的途径，包括环膨胀/环收缩过程中的两个步骤，第一步的活化能太高。相反，这种骨架重排似乎遵循外单骨架重排，其中初始环丙基金卡宾打开形成六元环。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• HETEROCYCLIC COMPOUNDS
  申请人：UNIVERSITY OF UTAH RESEARCH FOUNDATION

  公开号：US20150307455A1

  公开（公告）日：2015-10-29

  Described herein are methods for synthesizing heterocyclic, 8-membered ring structures. The methods may allow for preparation of highly substituted 8-membered rings. Also disclosed are heterocyclic, 8-membered ring compounds and pharmaceutical compositions comprising the compounds.
• US9102683B2
  申请人：——

  公开号：US9102683B2

  公开（公告）日：2015-08-11