1-bromomethylsulfinyl-4-chlorobenzene | 38325-81-4

• 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: 1-bromomethylsulfinyl-4-chlorobenzene
• 英文别名: 4-Chloro-1-(bromomethylsulfinyl)-benzene；α-Brommethyl-p-chlorphenylsulfoxid；1-(bromomethylsulfinyl)-4-chlorobenzene
• CAS: 38325-81-4
• 化学式: C₇H₆BrClOS
• 分子量: 253.547
• InChiKey: NREWMOFWMRQRPT-UHFFFAOYSA-N

物化性质

• 沸点：
  348.9±27.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-bromomethylsulfinyl-4-chlorobenzene 在 aluminum oxide 、 dicobalt octacarbonyl 作用下， 以 正己烷 为溶剂， 以100%的产率得到对-氯苯基甲基亚砜
  参考文献：
  名称：

  Selective dehalogenation of .alpha.-bromo sulfoxides by dicobalt octacarbonyl on alumina

  摘要：

  DOI：

  10.1021/jo00171a047
• 作为产物：
  描述：

  (bromomethyl)(4-chlorophenyl)sulfane 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以84%的产率得到1-bromomethylsulfinyl-4-chlorobenzene
  参考文献：
  名称：

  Pyrimidinones as reversible metaphase arresting agents

  摘要：

  5-Halo-N(1)-substituted 2(1H)-pyrimidinones have the ability to cause reversible arrest of mitosis during metaphase, Highly active compounds have a heteroatom (O, S or N) in the beta-position of the N(1)-carbon chain which is further substituted by an aryl group. In vitro data have been provided. It is suggested that reversible metaphase inhibitors can be used as synchronizing agents of cell-cycles by applying them in a sequential manner when a phase-specific cytotoxic drug is used in the treatment of diseases caused by uncontrolled rapidly proliferating cells. The active compounds are prepared from 2-pyrimidinones by alkylation reactions. The key reactants are alpha-chloroalkyl ethers, sulfides and amides; methods for their syntheses have been described.

  DOI：

  10.1016/0223-5234(93)90014-6

文献信息

• Substituted pyrimidin-2-ones and the salts thereof
  申请人：Nyegaard & Co. A.S.

  公开号：US04596870A1

  公开（公告）日：1986-06-24

  Compounds of the general formula: ##STR1## (wherein X represents a halogen atom or a trifluoromethyl group; R.sup.1 and R.sup.2 independently represent a hydrogen atom or a lower alkyl group; Z is --O--, --S--, --SO--, --SO.sub.2 -- or the group --NR.sup.4 -- wherein R.sup.4 is as defined for R hereinafter or represents the group COR.sup.5 in which R.sup.5 represents a hydrogen atom or an optionally substituted aryl, heterocyclic, aralkyl, lower alkyl or lower alkoxy group; R represents a C.sub.6-10 carbocyclic aromatic group or a heterocyclic group containing a 5-9 membered unsaturated or aromatic heterocyclic ring which ring contains one or more heteroatoms selected from O, N and S and optionally carries a fused ring which carbocyclic or heterocyclic group may carry one or more C.sub.1-4 alkyl or phenyl groups, said groups being optionally substituted; or, where Z represents the group >NR.sup.4, the group --ZR may represent a heterocyclic ring optionally carrying a fused ring and/or optionally substituted as defined for R; and R.sup.3 represents a hydrogen atom or a lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower alkenoyl, C.sub.7-16 aralkyl or C.sub.6-10 arly group or a 5-9 membered unsaturated or aromatic heterocyclic ring); and, where acid or basic groups are present, the salts thereof; are useful in combating abnormal cell proliferation. The compounds of the invention are prepared by inter alia alkylation, ring closure and oxidation.

  通式为：##STR1## 的化合物（其中X代表卤素原子或三氟甲基基团；R.sup.1和R.sup.2分别代表氢原子或较低的烷基基团；Z为--O--，--S--，--SO--，--SO.sub.2 --或基团--NR.sup.4 --其中R.sup.4如下所定义或代表基团COR.sup.5，其中R.sup.5代表氢原子或可选择取代的芳香族、杂环、芳基烷基、较低的烷基或较低的烷氧基团；R代表C.sub.6-10碳环芳族或含有5-9个成员的不饱和或芳香杂环环，该环含有O、N和S中选定的一个或多个杂原子，并且可选择携带一个融合环的碳环或杂环基团，该碳环或杂环基团可以携带一个或多个C.sub.1-4烷基或苯基基团，这些基团可选择取代；或者，Z代表基团>NR.sup.4时，基团--ZR可以代表一个可选择携带一个融合环和/或可选择取代的杂环环，如R所定义；R.sup.3代表氢原子或较低的烷基、较低的烯基、较低的炔基、较低的烷酰基、较低的烯酰基、C.sub.7-16芳基烷基或C.sub.6-10芳基基团或一个5-9成员的不饱和或芳香杂环环）；并且，如有酸性或碱性基团存在，其盐；在对抗异常细胞增殖方面是有用的。该发明的化合物是通过烷基化、环闭合和氧化等方法制备的。
• Kinetics of nucleophilic substitution of α-halogeno-sulphoxides
  作者：M. Cinquini、D. Landini、A. Maia

  DOI：10.1039/c39720000734

  日期：——

  α-Halogenomethyl sulphoxides react with PrnO– and EtS– in PrnOH via SN2 substitution; α0halogenoethyl and isopropyl derivatives react more slowly: SN2 reactions are greatly retarded by steric effects and SN1 reactions by the effect of the SO group.

  α-卤代甲基亚砜通过S N 2取代与Pr n OH中的Pr n O –和EtS –反应；α0卤代乙基和异丙基衍生物的反应更慢：S N 2反应由于空间效应而受到极大的阻碍，而S N 1反应则受到SO基团的影响而受到阻碍。
• Nucleophilic substitution in α-halogeno-sulphoxides. Part II. Dependence of the reaction mechanism on structural factors and on the nature of nucleophile
  作者：Mauro Cinquini、Stefano Colonna、Dario Landini、Angela Maria Maia

  DOI：10.1039/p29760000996

  日期：——

  Nucleophilic substitutions on α-halogeno-sulphoxides proceed through two competitive mechanisms, a direct S52 substitution and an elimination–addition process. The prevalence of either of the paths depends on the structure of the substrate and on the nature of the nucleophile. SN2 Displacement occurs in the reaction of α-halogenoethyl sulphoxides with EtS–, while elimination-addition takes place in

  α-卤代亚砜上的亲核取代过程通过两个竞争机制进行，即直接S 5 2取代和消除加成过程。任一路径的普遍性取决于底物的结构和亲核试剂的性质。S N 2置换发生在α-卤代乙基亚砜与EtS –的反应中，而消除加成发生在这些底物与Pr n O –的反应中以及1-卤代-1-甲基乙基衍生物与两种亲核试剂的反应中。 。
• US4596870A
  申请人：——

  公开号：US4596870A

  公开（公告）日：1986-06-24
• US4705791A
  申请人：——

  公开号：US4705791A

  公开（公告）日：1987-11-10