3-Methylene-4-[1-tributylstannanyl-meth-(Z)-ylidene]-cyclopentane-1,1-dicarboxylic acid dimethyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-Methylene-4-[1-tributylstannanyl-meth-(Z)-ylidene]-cyclopentane-1,1-dicarboxylic acid dimethyl ester
• 化学式: C₂₃H₄₀O₄Sn
• 分子量: 499.278
• InChiKey: GAWXPKOBPODMCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-2-bromo-1-[(1S)-1-hydroxy-3-triethylsilylprop-2-ynyl]cyclohex-2-en-1-ol 、 3-Methylene-4-[1-tributylstannanyl-meth-(Z)-ylidene]-cyclopentane-1,1-dicarboxylic acid dimethyl ester 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 以35%的产率得到dimethyl (7R,10aS,12S)-7,12-dihydroxy-5-(triethylsilyl)-1,3,7,8,9,10,10a,11-octahydro-2H-6,7-methanobenzo[a]cyclopenta[d][8]annulene-2,2-dicarboxylate
  参考文献：
  名称：

  4-exo-digcyclocarbopalladation / 8pi电环化级联反应：可以快速进入ophiobolins和aleurodiscal的三环核心结构。

  摘要：

  DOI：

  10.1002/anie.200453773
• 作为产物：
  描述：

  二甲基-2.2-二(丙-2-炔基)丙二酸二乙酯 、 三正丁基氢锡 在 tris(dibenzylideneacetone)dipalladium (0) 作用下， 以 四氢呋喃 为溶剂， 生成 3-Methylene-4-[1-tributylstannanyl-meth-(Z)-ylidene]-cyclopentane-1,1-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Palladium catalysed tandem cyclisation–anion capture processes. Part 8 : In situ and preformed organostannanes. Carbamyl chlorides and other starter species

  摘要：

  A sequential one-pot process is reported involving in situ, palladium catalysed, formation of a series of tributylstannyl-1,2-carbo and heterocyclic dialkylidene-5-membered rings from the corresponding 1,6-diynes and Bu3SnH. These substrates and other organostannanes are then combined with carbamyl chlorides and iodobenzenes containing proximate alkene and alkynyl groups in palladium catalysed cyclisation-anion capture cascades affording a diverse range of heterocycles in good yield. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.11.045

文献信息

• 4-exo-dig and 5-exo-dig Cyclocarbopalladations: an expeditious solution toward molecular complexity?
  作者：Christophe Bour、Gaëlle Blond、Bahaâ Salem、Jean Suffert

  DOI：10.1016/j.tet.2006.06.116

  日期：2006.11

  The 4-exo-dig and 5-exo-dig cyclocarbopalladations have been efficiently used to produce molecular complexity in a straightforward manner. Strained 1,2-cyclobutanediols are rapidly obtained under microwave irradiation in high yields. In many cases, the cyclocarbopalladation cascade reaction is associated with a 6 or 8π electrocyclic reaction. During the process of the 5-exo-dig cyclocarbopalladation

  4- exo - dig和5- exo - dig环卡巴来合成已被有效地用于以简单的方式产生分子复杂性。在微波辐射下，可以高产率快速获得应变的1,2-环丁二醇。在许多情况下，环卡巴拉定级联反应与6或8π电环反应有关。在5-过程外型-挖cyclocarbopalladation上苯并环庚酮衍生物，芳族C-H活化导致乙烯基取代芳烃。蛇胆草和Aleurodiscal家族的天然产物的多环骨架可以从​​简单的起始原料中分几步制备。
• A Cascade Palladium-Mediated Cross-Coupling/Electrocyclization Approach to the Construction of Fused Bi- and Tricyclic Rings
  作者：S. B. Jennifer Kan、Edward A. Anderson

  DOI：10.1021/ol8007952

  日期：2008.6.5

  A versatile palladium-catalyzed cyclization/cross-coupling/electrocyclization strategy for the synthesis of fused bi- and tricyclic ring systems is described. Excellent yields of the polycyclic products are obtained with a range of tethering ring sizes and functionality, including an unprecedented 5,6,4,5-fused tetracycle. The reaction mechanism features two unusual palladium-mediated isomerizations

  描述了一种通用的钯催化的环化/交叉偶联/电环化策略，用于合成稠合的双环和三环系统。通过一系列的束缚环大小和功能性（包括前所未有的5,6,4,5-稠合四环），可获得优异的多环产物收率。在电环化之前，反应机理具有两个不同寻常的钯介导的异构化作用。
• Palladium catalysed tandem cyclisation–anion capture processes. Part 8 : In situ and preformed organostannanes. Carbamyl chlorides and other starter species
  作者：Usman Anwar、Mark R. Fielding、Ronald Grigg、Visuvanathar Sridharan、Christopher J. Urch

  DOI：10.1016/j.jorganchem.2005.11.045

  日期：2006.4

  A sequential one-pot process is reported involving in situ, palladium catalysed, formation of a series of tributylstannyl-1,2-carbo and heterocyclic dialkylidene-5-membered rings from the corresponding 1,6-diynes and Bu3SnH. These substrates and other organostannanes are then combined with carbamyl chlorides and iodobenzenes containing proximate alkene and alkynyl groups in palladium catalysed cyclisation-anion capture cascades affording a diverse range of heterocycles in good yield. (c) 2005 Elsevier B.V. All rights reserved.
• A 4-exo-dig Cyclocarbopalladation/8π Electrocyclization Cascade: Expeditious Access to the Tricyclic Core Structures of the Ophiobolins and Aleurodiscal
  作者：Bahaâ Salem、Jean Suffert

  DOI：10.1002/anie.200453773

  日期：2004.5.17