(thien-α-oylmethyl)triphenylarsonium bromide | 86486-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (thien-α-oylmethyl)triphenylarsonium bromide
• 英文别名: (2-thienoylmethyl)triphenylarsonium bromide；thienoylmethyltriphenylarsonium bromide；[2-Oxo-2-(thiophen-2-yl)ethyl](triphenyl)arsanium bromide；(2-oxo-2-thiophen-2-ylethyl)-triphenylarsanium;bromide
• CAS: 86486-33-1
• 化学式: Br*C₂₄H₂₀AsOS
• 分子量: 511.314
• InChiKey: VKEDBKLYFPARRX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (thien-α-oylmethyl)triphenylarsonium bromide 、 5-(4-methoxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 在 potassium fluoride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 以90%的产率得到trans-γ-(4-methoxyphenyl)-β-(thiophene-2-carbonyl)-γ-butyrolactone
  参考文献：
  名称：

  Highly stereoselective synthesis of β,γ-disubstituted and α,β,γ-trisubstituted butyrolactones

  摘要：

  beta,gamma-Disubstituted butyrolactones were produced effectively and steroeselectively from arsonium ylides generated in situ and substituted olefins. The transformation could be realized in one-pot or in two steps, which depended on the electronic properties of the olefins. With the adjustment of the solvent and in the presence of EtOH, alpha,beta,gamma-trisubstituted butyrolactones were also obtained in high yield from arsonium ylides and substituted olefins. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.094

文献信息

• Highly stereoselective construction of spiro[cyclopropane-1,4′-pyrazolin-5′-one]with 4-arylidene-3-methyl-1-phenyl-pyrazolin-5-one and arsonium ylide
  作者：Zhongjiao Ren、Weiguo Cao、Jie Chen、Yali Chen、Hongmei Deng、Min Shao、Danyi Wu

  DOI：10.1016/j.tet.2008.03.049

  日期：2008.5

  A highly stereoselective synthesis of exo-spiro[cyclopropane-1,4′-pyrazolin-5′-one] from 4-arylidene-3-methyl-1-phenyl-pyrazolin-5-one and arsonium bromide in the presence of base has been achieved. The triphenylarsine-catalyzed cyclopropanation of 4-arylidene-3-methyl-1-phenyl-pyrazolin-5-one with bromide in the presence of NaHCO3 has also been studied. Both exo and endo isomers were formed in this

  在碱存在下，由4-亚芳基-3-甲基-1-苯基-吡唑啉-5-酮和溴化砷高度立体选择性地合成exo -spiro [cyclopropane-1,4'-pyrazolin-5'-one]实现了。在NaHCO 3存在下，还研究了三苯ar催化四溴化亚芳基-3-甲基-1-苯基-1-吡唑啉-5-酮的环丙烷化反应。两个外和内切形成在该反应中的异构体。产物的结构通过IR，MS，1 H NMR，元素分析和X射线衍射分析来表征。
• Highly stereoselective synthesis of cyclopropyl heterocycles<i>via</i>cyclopropanation of olefin with arsonium salt
  作者：Zhongjiao Ren、Weiguo Cao、Weiqi Tong、Jie Chen、Changqing Wang

  DOI：10.1002/jhet.5570450105

  日期：2008.1

  An efficient and highly stereoselective approach for the preparation of highly functionalized cyclopropyl heterocycles via the cyclopropanation of olefines with arsonium salts in the presence of KF2H2O has been developed.

  已经开发了一种在KF2H 2 O存在下通过烯烃与砷盐的环丙烷化制备高官能化环丙基杂环的有效且高度立体选择性的方法。
• Facile, Highly Stereoselective Synthesis of Cyclopropyl Benzoimidazoles via Cyclopropanation of Olefin with Arsonium Ylides
  作者：Weiqi Tong、Changqing Wang、Wenwen Zhao、Jie Chen、Xiaoyu Wu、Min Zhang、Hongmei Deng、Min Shao、Zhongjiao Ren、Weiguo Cao

  DOI：10.1080/00397910902778019

  日期：2009.9.8

  Abstract A facile and highly stereoselective methodology for the preparation of highly functionalized trans-1,2-cyclopropanes containing benzoimidazolyl, cyano, aryl, and carbonyl groups 3 is described. Arsonium bromides 2 reacted with electron-deficient olefins 1 in the presence of KF·2H2O to provide 3 exclusively with high stereoselectivity in moderate to good yields.

  摘要描述了一种用于制备含有苯并咪唑基、氰基、芳基和羰基 3 的高度官能化的反式-1,2-环丙烷的简便且高度立体选择性的方法。在 KF·2H2O 存在下，溴化砷 2 与缺电子烯烃 1 反应，以中等至良好的产率专门提供具有高立体选择性的 3。
• A facile preparation of trans-1,2-cyclopropanes containing p-trifluoromethylphenyl group and its application to the construction of pyrazole and cyclopropane ring fused pyridazinone derivatives
  作者：Weiguo Cao、Hui Zhang、Jie Chen、Hongmei Deng、Min Shao、Lu Lei、Jiaxian Qian、Yuan Zhu

  DOI：10.1016/j.tet.2008.05.016

  日期：2008.7

  A facile methodology for the preparation of highly functionalized trans-1,2-cyclopropanes containing p-trifluoromethylphenyl group 3 is described. Arsonium bromides 1 reacted with electron-deficient olefins 2 in the presence of K2CO3 to provide 3 stereoselectively in moderate to good yields. This process has been successfully applied to the construction of cyclopropane ring fused pyridazinone derivatives

  描述了一种用于制备含有对-三氟甲基苯基3的高度官能化的反式-1,2-环丙烷的简便方法。鉮溴化物1与缺电子烯烃反应2中K的存在2 CO 3，以提供3在中度至良好的产率立体选择性。该方法已成功地应用于环丙烷环稠合的哒嗪酮衍生物4或吡唑衍生物5的构建。
• Stereoselective synthesis of highly substituted trans-2,3-dihydrofuran and trans-1,2-cyclopropane derivatives containing sulfonyl groups
  作者：Weiguo Cao、Hui Zhang、Jie Chen、Xiaohong Zhou、Min Shao、Mark C. McMills

  DOI：10.1016/j.tet.2007.10.073

  日期：2008.1

  trans-2,3-Dihydrofuran derivatives 3 and trans-1,2-cyclopropane derivatives 4 were prepared with high chemoselectivity and moderate overall chemical yield by the reaction of alpha,beta-unsaturated sulfones 1 with arsonium bromides 2 in the presence of potassium carbonate. The structures of products obtained were identified by IR, MS, (1)H NMR, elemental analysis, and X-ray diffraction analysis. (c) 2007 Elsevier Ltd. All rights reserved.