diethyl 2,2'-disulfanediylbis(4-(4-bromophenyl)-6-methylpyrimidine-5-carboxylate) | 1606128-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: diethyl 2,2'-disulfanediylbis(4-(4-bromophenyl)-6-methylpyrimidine-5-carboxylate)
• CAS: 1606128-31-7
• 化学式: C₂₈H₂₄Br₂N₄O₄S₂
• 分子量: 704.463
• InChiKey: CCPBXMIOMDAERA-UHFFFAOYSA-N

物化性质

• 熔点：
  121-122 °C
• 沸点：
  818.7±75.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  104.16
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  diethyl 2,2'-disulfanediylbis(4-(4-bromophenyl)-6-methylpyrimidine-5-carboxylate) 、 苯基三甲氧基硅烷 在 噻吩-2-甲酸亚铜(I) 、 四丁基氟化铵 、 palladium diacetate 、 三环己基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以65%的产率得到ethyl 4-(4-bromophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate
  参考文献：
  名称：

  钯催化铜促进的二杂芳基二硫化物作为亲电试剂的Hiyama型碳-碳交叉偶联反应

  摘要：

  二杂芳基二硫化物在钯催化的碳-碳交叉偶联反应中与芳基硅烷用作亲电试剂以实现 Hiyama 型反应。这种独特的转变显示出高反应性、优异的官能团耐受性和温和的反应条件，使其成为传统的碳-碳键构建交叉偶联方法的有吸引力的替代方法。

  DOI：

  10.1055/s-0036-1589116
• 作为产物：
  描述：

  5-ethoxycarbonyl-6-methyl-4-(4-bromophenyl)-3,4-dihydropyrimidin-2(1H)-thione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以84%的产率得到diethyl 2,2'-disulfanediylbis(4-(4-bromophenyl)-6-methylpyrimidine-5-carboxylate)
  参考文献：
  名称：

  化学选择性碳-碳交叉偶联通过二硫键钯催化铜介导的CS切割

  摘要：

  AbstractAn efficient method for carbon‐carbon bond formation is described. The process employs the palladium‐catalyzed copper‐mediated cross‐coupling of diheteroaryl disulfides with arylboronic acids or alkynes to deliver CC coupling products through unreactive CS bond cleavage. The scope of the coupling reactions, including both the disulfides and arylboronic acids or alkynes, are documented.magnified image

  DOI：

  10.1002/adsc.201300776

文献信息

• Copper(<scp>i</scp>) chloride promoted Csp²–N cross-coupling of 1,2-di(pyrimidin-2-yl) disulfides with amines: an efficient approach to obtain C2-amino functionalized pyrimidines
  作者：Kai-Jie Wei、Zheng-jun Quan、Zhang Zhang、Yu-xia Da、Xi-cun Wang

  DOI：10.1039/c5ob02535d

  日期：——

  The copper(I)-promoted cross-coupling of 1,2-di(pyrimidin-2-yl) disulfides with aromatic amines and aliphatic amines to deliver C–N coupling products in moderate to good yields is reported in this paper. Central to this strategy is the conversion of disulfides into aryl- and alkyl amines by a copper-promoted chemoselective C–S bond cleavage.

  本文报道了铜（Ⅰ）促进的1，2-二（嘧啶-2-基）二硫化物与芳族胺和脂族胺的交叉偶联，以中等至良好的产率提供了C-N偶联产物。该策略的核心是通过铜促进的化学选择性C–S键裂解将二硫化物转化为芳基和烷基胺。
• Direct C–H heteroarylation of azoles with 1,2-di(pyrimidin-2-yl)disulfides through C–S cleavage of disulfides
  作者：Kai-Jie Wei、Zheng-jun Quan、Zhang Zhang、Yu-xia Da、Xi-cun Wang

  DOI：10.1039/c6ra18997k

  日期：——

  The C-C bond constructtion via C-H bond functionliazaiotn of oxazoles/thiazoles and C-S bond cleavage of di(hetero)aryl disulfides is described. Central to this strategy is the conversion of disulfides into 2-heterocyclic...

  描述了通过恶唑/噻唑的CH键官能团的CC键构造和二（杂）芳基二硫化物的CS键裂解。该策略的核心是将二硫化物转化为2-杂环...
• Chemo-Controlled Cross-Coupling of Di(hetero)aryl Disulfides with Grignard Reagents: CC<i>vs.</i>CS Bond Formation
  作者：Bao-Xin Du、Zheng-Jun Quan、Yu-Xia Da、Zhang Zhang、Xi-Cun Wang

  DOI：10.1002/adsc.201400980

  日期：2015.4.13

  A general protocol for the chemoselectivity‐controlled CC and CS coupling reactions of di(hetero)aryl disulfides with Grignard reagents catalyzed by ferrocene and palladium acetate has been developed. Ferrocene favored the formation of CS coupled products at low temperature, whereas CC bond couplings were favored when palladium acetate was used. All the reactions proceeded with excellent chemoselectivity

  已开发了二（杂）芳基二硫化物与二茂铁和乙酸钯催化的格氏试剂的化学选择性控制的CC和CS偶联反应的通用方案。二茂铁有利于在低温下形成CS偶联产物，而当使用乙酸钯时则有利于CC键偶联。在温和的条件下，所有反应均以优异的化学选择性和良好的收率进行，并产生了具有吡啶和嘧啶支架的分子库。
• C-O and C-S coupling reaction of 1,2-di(pyrimidin-2-yl) disulfides with phenols/thiophenols promoted by copper(I) chloride
  作者：Ping Zhang、Yan Guo、Zheng-Jun Quan

  DOI：10.1002/hc.21397

  日期：2017.9

  C-O and C-S bonds formation by the cross-coupling reaction of 1,2-di(pyrimidin-2-yl) disulfides with phenols/thiophenols promoted by copper(I) chloride was established. It was discovered that variously substituted di(hetero)aryl disulfides and phenols were well tolerated. This strategy is the conversion of disulfides into hetero-aryl ethers and thioethers by a copper-promoted chemoselective C-S bond cleavage

  建立了通过氯化铜（I）促进的 1,2-二（嘧啶-2-基）二硫化物与苯酚/苯硫酚的交叉偶联反应形成 CO 和 CS 键的有效方案。发现各种取代的二（杂）芳基二硫化物和酚类具有良好的耐受性。该策略是通过铜促进的二硫化物的化学选择性 CS 键裂解，将二硫化物转化为杂芳基醚和硫醚。
• The palladium‐catalyzed C‐N cross‐coupling reaction of diheteroaryl disulfides with heterocyclic amines
  作者：Ming‐Xia Liu、Zhang Zhang、Zheng‐Jun Quan、Xi‐Cun Wang

  DOI：10.1002/aoc.4020

  日期：2018.2

  cross‐coupling reaction of 1, 2‐di(pyrimidin‐2‐yl) disulfides with heterocyclic amines including 2‐amino pyrimidines and 1,3,4‐thiadiazol‐2‐amines to deliver symmetrical C‐N coupling products in moderate to good yields is reported. This method provides an opportunity for synthesis of bioactive molecules and pharmaceutically interesting compounds containing heterocycle motifs. The reported protocol shows good functional

  1，2-二（嘧啶-2-基）二硫化物与杂环胺（包括2-氨基嘧啶和1,3,4-噻二唑-2-胺）的Pd催化交叉偶联反应可提供对称的C-N偶联产物据报道产量中等至良好。该方法为合成具有杂环基序的生物活性分子和可药用化合物提供了机会。报告的协议显示出良好的官能团兼容性，并提供了一种从杂环二硫化物制备C2氨基嘧啶衍生物的新策略。