5,5',6,6',7,7',8,8'-octahydro-1,1'-di(methylthio)-3,3'-biisoquinoline | 287102-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5,5',6,6',7,7',8,8'-octahydro-1,1'-di(methylthio)-3,3'-biisoquinoline
• 英文别名: 1,1'-Bis(methylsulfanyl)-5,5',6,6',7,7',8,8'-octahydro-3,3'-biisoquinoline；1-methylsulfanyl-3-(1-methylsulfanyl-5,6,7,8-tetrahydroisoquinolin-3-yl)-5,6,7,8-tetrahydroisoquinoline
• CAS: 287102-77-6
• 化学式: C₂₀H₂₄N₂S₂
• 分子量: 356.556
• InChiKey: OWLYPRNIQDFWOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5',6,6',7,7',8,8'-octahydro-1,1'-di(methylthio)-3,3'-biisoquinoline 在 potassium permanganate 、 四丁基溴化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 3.0h， 生成 1,1'-bis-pent-4-enyloxy-5,6,7,8,5',6',7',8'-octahydro-3,3'-biisoquinoline
  参考文献：
  名称：

  Ring-closing metathesis approach to symmetrical and unsymmetrical cycloakeno[c]fused 2,2′-bipyridine-based cyclophanes

  摘要：

  Ring-closing metathesis reactions of symmetrical and unsymmetrical cycloalkeno[c]fused 2,2'-bipyridines, substituted at the alpha and alpha' positions of the pyridine rings with sufficiently long alkenyl ethers, afforded 16-membered cyclophanes, possessing variously annulated 2,2'-bipyridine subunits. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.081
• 作为产物：
  描述：

  1-吡咯烷-1-环己烯 、 3,3'-bis(methylsulfanyl)-5,5'-bi-1,2,4-triazine 反应 15.0h， 以68%的产率得到5,5',6,6',7,7',8,8'-octahydro-1,1'-di(methylthio)-3,3'-biisoquinoline
  参考文献：
  名称：

  通过 5,5'-bi-1,2,4-三嗪的逆电子需求 Diels-Alder 反应生成对称和不对称环烯 [c] 稠合 2,2'-联吡啶配体的简便途径

  摘要：

  描述了一系列 6,6'-双官能化对称环烯基 [c] 稠合 2,2'-联吡啶 4a-h 或不对称环烯基 [c] 稠合 2,2'-联吡啶 6a-g。它们是通过 3,3'-二取代 5,5'-bi-1,2,4-三嗪 2a,b 与环状烯胺 3a-d 的 Diels-Alder 反应制备的。1-乙烯基咪唑 (3e) 与 2a 的区域选择性反应导致 5-(2-吡啶基)-1,2,4-三嗪 9 与环状烯胺 3a-d 发生 Diels-Alder 反应得到不对称的 2,2'-连接有一个环烯烃环的联吡啶 10a-d。

  DOI：

  10.1055/s-2003-41452

文献信息

• A novel one-pot synthesis of annulated 2,2′-bipyridine ligands by inverse electron demand Diels–Alder reaction of 5,5′-bi-1,2,4-triazines
  作者：Andrzej Rykowski、Danuta Branowska、Joanna Kielak

  DOI：10.1016/s0040-4039(00)00436-6

  日期：2000.5

  The Diels–Alder reaction of 5,5′-bi-1,2,4-triazines with cyclic enamines in the absence of a solvent leads to a range of symmetrical, annulated 2,2′-bipyridines in good yield. When the reaction is carried out in boiling dioxane only 5-(heteroaryl)1,2,4-triazines are formed. The latter, bearing methylsulfanyl substituents, are oxidized with potassium permanganate to the corresponding methylsulfonyl

  5,5'-联-1,2,4-三嗪与环状烯胺的狄尔斯-阿尔德反应在不存在溶剂的情况下可产生一系列对称的，环状的2,2'-联吡啶，并具有良好的收率。当反应在沸腾的二恶烷中进行时，仅形成5-（杂芳基）1,2,4-三嗪。后者带有甲基硫烷基取代基，被高锰酸钾氧化成相应的甲基磺酰基衍生物，很容易与不同的烯胺进行Diels-Alder反应，生成不对称的环状2,2'-联吡啶。
• A facile S-transalkylation of 2,2′-bipyridine alkyl sulfides—a new tool for the synthesis of annulated biheterocycles
  作者：Danuta Branowska、Andrzej Rykowski、Waldemar Wysocki

  DOI：10.1016/j.tetlet.2005.07.062

  日期：2005.9

  A simple and efficient synthesis of annulated 2,2′-bipyridinium salts with attached dihydrothiazole or dihydro-1,3-thiazine rings has been developed through tandem S-transalkylation/intramolecular ring closure of 2,2′-bipyridine alkyl sulfides. The structures were confirmed by X-ray crystallographic analysis.

  通过串联2,2'-联吡啶烷基硫化物的S-烷基转移/分子内环闭合，已经开发了一种简单有效的方法，用于合成带有连接的二氢噻唑或二氢-1,3-噻嗪环的环状2,2'-联吡啶鎓盐。通过X射线晶体学分析确认了结构。
• ——
  作者：Z. Karczmarzyk、D. Branowska、A. Rykowski、A. Fruziński

  DOI：10.1023/a:1020257208112

  日期：——

  Title compound, C(2)0H(2)4N(2)S(2), crystallizes in the orthorhombic system, space group Pbca, with cell constants a = 5.1968(5) Angstrom, b = 15.6692(11) Angstrom, c = 22.3881(11) Angstrom , Z = 4, T = 293 K, D(c)al = 1.299 g cm(-)3. The structure was solved by direct methods and refined to R value of 0.0465 for 1566 reflections. Two methylthio-octahydroisoquinoline parts of molecule are related by the center of symmetry and possess the trans conformation. This conformation is more energetically stable than cis but the molecule can rotate about the C(6)-C(6') central bond at room temperature (molecular mechanics calculations). There is a short intramolecular contact C(5)-H(51) . . . N(1') in the molecule. The molecules in the crystal form molecular layers parallel to (001) crystallographic plane and the molecular packing is determined by the van der Waals forces only.
• A Facile Route to Symmetrical and Unsymmetrical Cycloalkeno[<i>c</i>]fused 2,2′-Bipyridine Ligands via Inverse Electron Demand Diels-Alder Reaction of 5,5′-bi-1,2,4-Triazines
  作者：Danuta Branowska

  DOI：10.1055/s-2003-41452

  日期：——

  A series of 6,6'-bisfunctionalized symmetrical cycloalkeno[c]fused 2,2'-bipyridines 4a-h or unsymmetrical cycloalkeno[c]fused 2,2'-bipyridines 6a-g is described. They were prepared by the Diels-Alder reaction of 3,3'-disubstituted 5,5'-bi-1,2,4-triazines 2a,b with cyclic enamines 3a-d. The regioselective reaction of 1-vinylimidazole (3e) with 2a leads to 5-(2-pyridyl)-1,2,4-triazine 9 which undergoes

  描述了一系列 6,6'-双官能化对称环烯基 [c] 稠合 2,2'-联吡啶 4a-h 或不对称环烯基 [c] 稠合 2,2'-联吡啶 6a-g。它们是通过 3,3'-二取代 5,5'-bi-1,2,4-三嗪 2a,b 与环状烯胺 3a-d 的 Diels-Alder 反应制备的。1-乙烯基咪唑 (3e) 与 2a 的区域选择性反应导致 5-(2-吡啶基)-1,2,4-三嗪 9 与环状烯胺 3a-d 发生 Diels-Alder 反应得到不对称的 2,2'-连接有一个环烯烃环的联吡啶 10a-d。
• Ring-closing metathesis approach to symmetrical and unsymmetrical cycloakeno[c]fused 2,2′-bipyridine-based cyclophanes
  作者：D. Branowska、A. Rykowski

  DOI：10.1016/j.tet.2005.08.081

  日期：2005.11

  Ring-closing metathesis reactions of symmetrical and unsymmetrical cycloalkeno[c]fused 2,2'-bipyridines, substituted at the alpha and alpha' positions of the pyridine rings with sufficiently long alkenyl ethers, afforded 16-membered cyclophanes, possessing variously annulated 2,2'-bipyridine subunits. (c) 2005 Elsevier Ltd. All rights reserved.