4-(4-bromobenzylsulfanyl)benzoic acid

• 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: 4-(4-bromobenzylsulfanyl)benzoic acid
• 英文别名: 4-(4-bromobenzylthio)benzoic acid；4-[(4-Bromophenyl)methylsulfanyl]benzoic acid
• 化学式: C₁₄H₁₁BrO₂S
• mdl: MFCD11522418
• 分子量: 323.21
• InChiKey: XOFHSDQDHHXXPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴苯甲酸 、 对溴溴苄 在 正丁基锂 、 sulfur 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以89%的产率得到4-(4-bromobenzylsulfanyl)benzoic acid
  参考文献：
  名称：

  从芳基溴化物轻松一锅合成烷基芳基硫化物

  摘要：

  报道了一种方便的一锅合成方法，该方法由各种烷基卤和芳基硫醇锂通过直接卤素-锂交换原位制备形成烷基芳基硫醚。尤其是，该方法克服了先前报告中遇到的许多问题。它非常快速，无催化剂，并且不涉及使用不稳定的芳基硫醇。

  DOI：

  10.1021/jo049758h

文献信息

• Mercaptobenzoic acid-palladium(0) complexes as active catalysts for S-benzylation with benzylic alcohols via (η³-benzyl)palladium(<scp>ii</scp>) cations in water
  作者：Hidemasa Hikawa、Isao Azumaya

  DOI：10.1039/c4ob00688g

  日期：——

  of the respective substituents. From the slope, negative rho values are obtained, suggesting that there is a build-up of positive charge in the transition state. Water plays an important role in the catalytic system for sp(3) C-O bond activation and stabilization of the activated Pd(II) cation species. The catalytic system can be performed using only 2.5 mol% Pd2(dba)3 without the phosphine ligand or

  巯基苯甲酸-钯（0）配合物通过水中的（eta（3）-苄基）钯（II）阳离子对苄基醇进行S-苄基化反应显示出高催化活性。值得注意的是，这些钯（0）配合物可以在形成活性（eta（3）-苄基）钯（II）阳离子配合物，然后进行S-苄基化过程中发挥重要作用。Hammett对各种取代醇进行S-苄基化反应的速率常数的研究表明，log（kX / kH）与各个取代基的sigma（+）值之间具有良好的相关性。从斜率可以得到负rho值，这表明在过渡态中会积聚正电荷。水在sp（3）CO键活化和活化Pd（II）阳离子物种的稳定化催化体系中起着重要作用。催化系统只能使用2进行。
• Palladium-catalyzed S-benzylation of unprotected mercaptobenzoic acid with benzyl alcohols in water
  作者：Hidemasa Hikawa、Yuusaku Yokoyama

  DOI：10.1039/c2ob25091h

  日期：——

  Palladium-catalyzed S-benzylation of unprotected mercaptobenzoic acids with benzyl alcohols gave only S-benzylated mercaptobenzoic acids in good yields. Water may play an important role for the smooth generation of the (η3-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.

  钯催化下，用苄醇对未保护的硫代苯甲酸进行S-苄基化反应仅生成S-苄基化硫代苯甲酸，且产率良好。水可能在通过激活苄醇的羟基生成(η3-苄基)钯物种的过程中特别重要。
• PROCESS FOR ALKYL ARYL SULFIDE DERIVATIVES AND NEW SULFIDE COMPOUNDS
  申请人：Kang Heonjoong

  公开号：US20090264660A1

  公开（公告）日：2009-10-22

  An alkyl aryl sulfide of Chemical Formula (III) is prepared by substituting an aryl halogen compound of Chemical Formula (I) with an alkyl lithium organometallic reagent. The sulfide is subsequently reacted with a compound of Chemical Formula (II). Alternatively an aryl halogen compound of Chemical Formula (I) is reacted with Grignard reagent to protect the hydrogen-donating substituent, and then reacted with an alkyl lithium organometallic reagent, and subsequently with sulfur and a compound of Chemical Formula (II). An alkyl aryl sulfide of Chemical Formula (III) is prepared via a one-step reaction without separation or purification of an intermediate compound from various aryl halogen compounds.
• A Facile One-Pot Synthesis of Alkyl Aryl Sulfides from Aryl Bromides
  作者：Jungyeob Ham、Inho Yang、Heonjoong Kang

  DOI：10.1021/jo049758h

  日期：2004.4.1

  one-pot synthetic method for the formation of alkyl aryl sulfides from various alkyl halides and lithium aryl thiolates that are prepared in situ by direct halogen−lithium exchange is reported. In particular, the method overcomes many of the problems encountered in previous reports; it is very quick, catalyst-free, and does not involve use of unstable aryl thiols.

  报道了一种方便的一锅合成方法，该方法由各种烷基卤和芳基硫醇锂通过直接卤素-锂交换原位制备形成烷基芳基硫醚。尤其是，该方法克服了先前报告中遇到的许多问题。它非常快速，无催化剂，并且不涉及使用不稳定的芳基硫醇。