2-(benzenesulfonylmethyl)cyclopent-2-en-1-one | 123487-98-9

• 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-(benzenesulfonylmethyl)cyclopent-2-en-1-one
• CAS: 123487-98-9
• 化学式: C₁₂H₁₂O₃S
• 分子量: 236.291
• InChiKey: DLMKLBHEWHCVFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(benzenesulfonylmethyl)cyclopent-2-en-1-one 在 正丁基锂 、 silica gel 、 lithium bromide 作用下， 以 正己烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 98.33h， 生成 (2R,3R)-2-Phenylsulfanylmethyl-3-vinyl-cyclopentanone
  参考文献：
  名称：

  Asymmetric synthesis of 3-substituted 2-exo-methylenealkanones by addition-elimination reaction using a chiral leaving group and organometallic nucleophiles

  摘要：

  A novel diastereodifferentiating addition-elimination reaction of (S)-2-[[2-(methoxymethyl)-1-pyrrolidinyl]methyl]-2-alken-1-ones with organometallic reagents such as organocuprates and organozincates afforded optically active 3-substituted 2-methylenealkanones with high enantiomeric purity. The enantiomeric excess (ee) of the products in this asymmetric induction reaction involving 1,5-transfer of stereogenicity was highly dependent on the structure of the enone substrates and the type of organometallic reagents, chiral auxiliaries, and added Lewis acids: (i) the use of lithium diorganocuprates (R2CuLi) led to the highest ee's, (ii) in the reaction with R2CuLi the ee decreased in the following order by varying their structure of the main framework of the enones, cycloheptenones (96-97% ee) > cyclohexenones (95% ee) > cyclopentenones (82-85% ee) > acyclic enones (55-70% ee), (iii) the addition of LiBr as the external Lewis acid in the reaction with R2CuLi did not affect the ee, whereas that of ZnBr2 or MgBr2 decreased the ee by 5% or considerably more, respectively, and (iv) the existence of the methoxy oxygen atom in the chiral auxiliary was essential to achieve high ee's. The origin of the observed high and low ee's was rationalized by considering plausible transition state models.

  DOI：

  10.1021/jo00044a026
• 作为产物：
  描述：

  2-[(苯基硫醇)甲基]-2-环戊烯-1-酮 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 以97%的产率得到2-(benzenesulfonylmethyl)cyclopent-2-en-1-one
  参考文献：
  名称：

  亲核试剂选择性取代环状α-（硝基烷基）-或α-（苯磺酰基烷基）烯酮中的硝基或磺酰基

  摘要：

  环状α-（硝基烷基）烯酮和α-（苯磺酰基烷基）烯酮通过相对较软的硫，氮和碳亲核试剂对硝基进行区域选择性取代。

  DOI：

  10.1016/s0040-4020(01)89067-0