2-bromo-dithiobenzoic acid methyl ester | 711603-36-0

• 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: 2-bromo-dithiobenzoic acid methyl ester
• 英文别名: 2-bromo-dithiobenzoic acid S-methyl ester；methyl 2-bromobenzodithioate；Methyl 2-bromobenzene-1-carbodithioate；methyl 2-bromobenzenecarbodithioate
• CAS: 711603-36-0
• 化学式: C₈H₇BrS₂
• 分子量: 247.18
• InChiKey: VBQVSHNLDOYKDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1,2-二苯基乙二胺 、 2-bromo-dithiobenzoic acid methyl ester 在 mercury(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以72%的产率得到(4R,5R)-2-(2-bromo-phenyl)-4,5-diphenyl-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  An efficient method for the synthesis of enantiopure phosphine–imidazoline ligands: application to the Ir-catalyzed hydrogenation of imines

  摘要：

  Phosphine-imidazoline ligands 8, and the derivatives 16 and 17, which have electron-withdrawing or electron-donating groups in the aminic nitrogen, were synthesized from 2-aryl-imidazo lines, which have previously been obtained from dithioesters. The coordination of ligand 8 to Ir(I) was studied and the molecular structure of the [Ir(eta(4) -COD)8]BF4 (COD = 1,5-cyclooctadiene) determined through X-ray diffraction. The in situ prepared Ir(I)/phosphine-imidazo line catalysts were tested in the asymmetric hydrogenation of ketimines in order to evaluate the influence of the electronic parameters of the ligand on the catalytic reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.013
• 作为产物：
  描述：

  2-溴苯甲酰氯 在 劳森试剂 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 25.0h， 生成 2-bromo-dithiobenzoic acid methyl ester
  参考文献：
  名称：

  An efficient method for the synthesis of enantiopure phosphine–imidazoline ligands: application to the Ir-catalyzed hydrogenation of imines

  摘要：

  Phosphine-imidazoline ligands 8, and the derivatives 16 and 17, which have electron-withdrawing or electron-donating groups in the aminic nitrogen, were synthesized from 2-aryl-imidazo lines, which have previously been obtained from dithioesters. The coordination of ligand 8 to Ir(I) was studied and the molecular structure of the [Ir(eta(4) -COD)8]BF4 (COD = 1,5-cyclooctadiene) determined through X-ray diffraction. The in situ prepared Ir(I)/phosphine-imidazo line catalysts were tested in the asymmetric hydrogenation of ketimines in order to evaluate the influence of the electronic parameters of the ligand on the catalytic reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.013

文献信息

• Efficient New Protocol to Synthesize Aromatic and Heteroaromatic Dithioesters
  作者：Serge Masson、Isabelle Abrunhosa、Mihaela Gulea

  DOI：10.1055/s-2004-822311

  日期：——

  A very efficient, high yielding procedure to synthesize substituted aromatic and heteroaromatic dithioesters is described. It involves the reaction between (phenylsulfonyl)methyl (hetero)aromatic derivatives and elemental sulfur in basic medium, followed by alkylation.

  描述了一种高效、高产的合成取代芳香和杂芳香二硫酯的方法。该方法包括在碱性介质中（苯磺酰）甲基（杂）芳香衍生物与硫元素反应，随后进行烷基化。
• Synthesis and photoreactivity of aryl substituted 4,5-dithienyl[1,3]dithiol-2-ones
  作者：Anton Blencowe、Angela Maria Celli、Donato Donati、Wayne C. Hayes、Claire Martin、Patrick J. Murphy、Fabio Ponticelli、Jessica K. Melville-Richards

  DOI：10.1016/j.tet.2009.03.015

  日期：2009.5

  UV irradiation of hitherto unknown 4,5-bis-benzol[b]thiophen-3-yl-[1,3]dithiol-2-one gave 3-(3-benzo[b]thienyl)-thieno[3,4-c]benzo[ e][1,2]dithine by loss of carbon monoxide and rearrangement, whereas 4,5-bis-(2-bromo-phenyl)-[1,3]dithiol-2-one gave a polymeric material containing S-S bridges. The Structures of both photoproducts were demonstrated on the basis of chemical behaviour and/or X-ray diffraction. (C) 2009 Elsevier Ltd. All rights reserved.
• An efficient method for the synthesis of enantiopure phosphine–imidazoline ligands: application to the Ir-catalyzed hydrogenation of imines
  作者：Ester Guiu、Carmen Claver、Jordi Benet-Buchholz、Sergio Castillón

  DOI：10.1016/j.tetasy.2004.09.013

  日期：2004.11

  Phosphine-imidazoline ligands 8, and the derivatives 16 and 17, which have electron-withdrawing or electron-donating groups in the aminic nitrogen, were synthesized from 2-aryl-imidazo lines, which have previously been obtained from dithioesters. The coordination of ligand 8 to Ir(I) was studied and the molecular structure of the [Ir(eta(4) -COD)8]BF4 (COD = 1,5-cyclooctadiene) determined through X-ray diffraction. The in situ prepared Ir(I)/phosphine-imidazo line catalysts were tested in the asymmetric hydrogenation of ketimines in order to evaluate the influence of the electronic parameters of the ligand on the catalytic reaction. (C) 2004 Elsevier Ltd. All rights reserved.