3-(tri-n-butylstannyl)-4-(1-methylethoxy)cyclobut-3-ene-1,2-dione 2-(ethylene acetal) | 129034-74-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(tri-n-butylstannyl)-4-(1-methylethoxy)cyclobut-3-ene-1,2-dione 2-(ethylene acetal)
• 英文别名: 3-methyl-4-(tri-n-butylstannyl)-3-cyclobutene-1,2-dione-1-ethylene acetal；4-Methyl-3-(tri-n-butylstannyl)-3-cyclobutene-1,2-dione 2-ethylene acetal；3-(tri-n-butylstannyl)-4-methyl-3-cyclobutene-1,2-dione 2-(ethylene acetal)；2,2-Ethylenedioxy-4-methyl-3-(tri-n-butylstannyl)cyclobut-3-ene-1-one
• CAS: 129034-74-8
• 化学式: C₁₉H₃₄O₃Sn
• 分子量: 429.187
• InChiKey: DGEYGZGTGCADGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  438.5±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  3-(tri-n-butylstannyl)-4-(1-methylethoxy)cyclobut-3-ene-1,2-dione 2-(ethylene acetal) 在 copper(l) iodide 、 benzoylchlorobis(triphenylphosphine)palladium(II) 硫酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 3-methyl-4-phenylcyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  3-Stannylcyclobutenediones as nucleophilic cyclobutenedione equivalents. Synthesis of substituted cyclobutenediones and cyclobutenedione monoacetals and the beneficial effect of catalytic copper iodide on the Stille reaction

  摘要：

  DOI：

  10.1021/jo00306a012

文献信息

• Optimized Stille coupling reactions catalyzed by palladium on carbon with CuI as cocatalyst
  作者：Gregory P. Roth、Vittorio Farina、Lanny S. Liebeskind、Eduardo Peña-Cabrera

  DOI：10.1016/0040-4039(95)00232-2

  日期：1995.3

  The coupling reaction of aryl and vinyl iodides, bromides, and triflates with organostannanes can be effectively conducted using palladium on carbon as a source of Pd0. The yield and rate of reaction are significantly affected by the addition of copper iodide as co-catalyst and triphenylarsine as ligand.

  使用钯/碳作为Pd 0的来源，可以有效地进行芳基和乙烯基碘化物，溴化物和三氟甲磺酸酯与有机锡的偶联反应。加入碘化铜作为助催化剂和加入三苯基s作为配体会显着影响反应的收率和反应速率。
• 4,4'-Bi(cyclobutene-1,2-diones): bisquaryls
  作者：Lanny S. Liebeskind、Marvin S. Yu、Richard H. Yu、Jianying Wang、Karl S. Hagen

  DOI：10.1021/ja00073a021

  日期：1993.10

  oxidative dimerization of (tri-n-butylstannyl)cyclobutene-1,2-diones (providing symmetrically substituted bisquaryls) or by a palladium-copper cocatalyzed cross-coupling of 3-substituted-4-(tri-n-butylstannyl)-3-cyclobutene-1,2-diones with 3-halo-4-substituted-3-cyclobutene-1,2-diones (providing a route to unsymmetrically substituted bisquaryls). The novel parent bisquaric acid is a very strong BrOnsted acid

  4,4'-Bi(cyclobutene-1,2-diones)，一种衍生自方酸的新型化合物，此处命名为双方芳基，首次通过钯催化的（三正丁基甲锡烷基）环丁烯氧化二聚反应制备-1,2-二酮（提供对称取代的双四芳基）或通过钯-铜共催化的 3-取代-4-（三正丁基甲锡烷基）-3-环丁烯-1,2-二酮与 3-卤素的交叉偶联-4-取代-3-环丁烯-1,2-二酮（提供不对称取代双四芳基的途径）。新的母体双方酸是一种非常强的布朗斯台德酸，显然在溶解时完全电离；仅观察到一个 pK a 值 (pK a = -4.49)
• Antibiotic C-3 cyclobutenedione substituted (1-carba) cephalosporin
  申请人：Bristol-Myers Squibb Company

  公开号：US05169843A1

  公开（公告）日：1992-12-08

  A compound for formula I ##STR1## wherein X is sulfur or CH.sub.2 ; R.sup.1 is hydrogen, hydroxy, amino, C.sub.1-6 alkyl, C.sub.2-5 alkenyl, C.sub.2-6 alkynyl, phenyl optionally substituted with one to three C.sub.1-6 alkyl, C.sub.1-6 alkyloxy or hydroxy, C.sub.1-6 alkylthio, phenylthio optionally substituted with one to three C.sub.1-6 alkyl or C.sub.1-6 alkyloxy on the phenyl ring, phenylmethyloxy optionally substituted with one to three C.sub.1-6 alkyl or C.sub.1-6 alkyloxy on the phenyl ring, 1-morpholino, C.sub.1-6 alkyloxy, C.sub.2-6 alkenylmethyloxy, C.sub.3-6 alkynylmethyloxy, C.sub.1-6 alkylamino, C.sub.1-6 dialkylamino or a radical selected from the group consisting of ##STR2## in which n is 0 to 3, R.sup.5 is C.sub.1-6 alkyl or hydrogen, and R.sup.3 and R.sup.4 are independently C.sub.1-6 alkyl; R.sup.2 is hydrogen, a conventional amino protecting group or an acyl group; R.sup.0 is hydrogen or a conventional carboxy protecting group, or --CO.sub.2 R.sup.0 taken together forms a physiologically hydrolyzable ester; or pharmaceutically acceptable salts or solvates thereof.

  化合物的化学式为I ##STR1## 其中 X 为硫或CH.sub.2；R.sup.1 为氢、羟基、氨基、C.sub.1-6烷基、C.sub.2-5烯基、C.sub.2-6炔基、苯基，所述苯基可选用1-3个C.sub.1-6烷基、C.sub.1-6烷氧基或羟基、C.sub.1-6烷硫基，苯硫基可选用1-3个C.sub.1-6烷基或C.sub.1-6烷氧基取代苯环，苯甲氧基可选用1-3个C.sub.1-6烷基或C.sub.1-6烷氧基取代苯环，1-吗啉基、C.sub.1-6烷氧基、C.sub.2-6烯基甲氧基、C.sub.3-6炔基甲氧基、C.sub.1-6烷基氨基、C.sub.1-6二烷基氨基或从下列组中选择的基团之一：##STR2## 其中n为0至3，R.sup.5为C.sub.1-6烷基或氢，R.sup.3和R.sup.4独立地为C.sub.1-6烷基；R.sup.2为氢、传统的氨基保护基或酰基；R.sup.0为氢或传统的羧基保护基，或--CO.sub.2R.sup.0结合形成生理水解酯；或其药学上可接受的盐或溶剂。
• Antibiotic C-3 cyclobutenedione substituted (1-carba)cephalosporin
  申请人：Bristol-Myers Squibb Co.

  公开号：US05106842A1

  公开（公告）日：1992-04-21

  A compound of formula I ##STR1## wherein X is sulfur or CH.sub.2 ; R.sup.1 is hydrogen, hydroxy, amino, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, phenyl optionally substituted with one to three C.sub.1-6 alkyl, C.sub.1-6 alkyloxy or hydroxy, C.sub.1-6 alkylthio, phenylthio optionally substituted with one to three C.sub.1-6 alkyl or C.sub.1-6 alkyloxy on the phenyl ring, phenylmethyloxy optionally substituted with one to three C.sub.1-6 alkyl or C.sub.1-6 alkyloxy on the phenyl ring, 1-morpholino, C.sub.1-6 alkyloxy, C.sub.2-6 alkenylmethyloxy, C.sub.3-6 alkynylmethyloxy, C.sub.1-6 alkylamino, C.sub.1-6 dialkylamino or a radical selected from the group consisting of ##STR2## in which n is 0 to 3, R.sup.5 is C.sub.1-6 alkyl or hydrogen, and R.sup.3 and R.sup.4 are independently C.sub.1-6 alkyl; R.sup.2 is hydrogen, a conventional amino protecting group or an acyl group; R.sup.0 is hydrogen or a conventional carboxy protecting group, or --CO.sub.2 R.sup.0 taken together forms a physiologically hydrolyzable ester; or pharmaceutically acceptable salts or solvates thereof.

  化合物I的公式为##STR1## 其中X为硫或CH.sub.2; R.sup.1为氢，羟基，氨基，C.sub.1-6烷基，C.sub.2-6烯基，C.sub.2-6炔基，苯基，该苯基上可选地被1-3个C.sub.1-6烷基，C.sub.1-6烷氧基或羟基取代，苯硫基，该苯硫基上可选地被1-3个C.sub.1-6烷基或C.sub.1-6烷氧基取代，苯甲氧基，该苯甲氧基上可选地被1-3个C.sub.1-6烷基或C.sub.1-6烷氧基取代，1-吗啉基，C.sub.1-6烷氧基，C.sub.2-6烯基甲氧基，C.sub.3-6炔基甲氧基，C.sub.1-6烷基氨基，C.sub.1-6二烷基氨基或从##STR2## 组成的基，其中n为0-3，R.sup.5为C.sub.1-6烷基或氢，R.sup.3和R.sup.4独立地为C.sub.1-6烷基; R.sup.2为氢，传统的氨基保护基或酰基; R.sup.0为氢或传统的羧基保护基，或--CO.sub.2 R.sup.0在一起形成生理可水解的酯; 或其药学上可接受的盐或溶剂化物。
• Preparation of 3-acyl-3-cyclobutene-1,2-diones and some related monoacetals
  作者：Lanny S. Liebeskind、Marvin S. Yu、Richard W. Fengl

  DOI：10.1021/jo00065a016

  日期：1993.6

  3-(Tri-n-butylstannyl)-3-cyclobutene-1,2-diones and 4-methyl-3-(tri-n-butylstannyl)-3-cyclobutene-1,2-dione 2-ethylene acetal participate in palladium/copper-cocatalyzed cross-coupling with acyl halides and in palladium-catalyzed carbonylative cross-coupling with aryl/heteroaryl iodides. The derived 3-acyl-3-cyclobutenediones and cyclobutenedione monoacetals should extend the potential of cyclobutenedione-based synthetic organic methodology.