2-(Phenylsulfonyl)-2-cycloheptenone | 169691-02-5

• 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-(Phenylsulfonyl)-2-cycloheptenone
• 英文别名: 2-(Benzenesulfonyl)cyclohept-2-en-1-one
• CAS: 169691-02-5
• 化学式: C₁₃H₁₄O₃S
• 分子量: 250.318
• InChiKey: MDBTXICVTXIKPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(bromomethyl)-3-(phenylsulfonyl)-1-propene 、 2-(Phenylsulfonyl)-2-cycloheptenone 在 lithium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以50%的产率得到(1β,3aβ,8aβ)-2-Methylene-<1,3a-bis(phenylsulfonyl)>octahydro-1H-azulen-4-one
  参考文献：
  名称：

  Cyclopentannulations leading to the synthesis of bicyclic conjugated enediones.

  摘要：

  Base-induced reactions of 1-(phenylsulfonyl)-2-methylene-3-bromopropane (4) with 2-(phenylsulfonyl)-2-cycloalkenones 8a-d were investigated with the ultimate purpose to develop a route leading to bicyclic conjugated enediones. Low-temperature, fast-quenched reactions led generally to open-chain adducts, while increase of temperature and addition of HMPA resulted in subsequent ring closure by a tandem Michael-S(N)2 process. The stereochemical features of the bicyclo[3.3.0]octanes 11 and 12, bicyclo[4.3.0]nonanes 18 and 19, bicyclo[5.3.0]decanes 22 and 23, and bicyclo[6.3.0]-undecanes 26-28 thus obtained have been determined. Ozonolysis and silica-induced elimination of the tertiary phenylsulfonyl group converted stereoselectively the above products into the desired enediones: pentalenedione 29, indenedione 30, azulenedione 32 and cyclopentacyclooctenedione 33, respectively.

  DOI：

  10.1021/jo00121a035
• 作为产物：
  描述：

  2-(phenylsulfinyl)cycloheptanone 在 sodium periodate 、 甲烷磺酸 、 乙酸酐 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 2-(Phenylsulfonyl)-2-cycloheptenone
  参考文献：
  名称：

  Cyclopentannulations leading to the synthesis of bicyclic conjugated enediones.

  摘要：

  Base-induced reactions of 1-(phenylsulfonyl)-2-methylene-3-bromopropane (4) with 2-(phenylsulfonyl)-2-cycloalkenones 8a-d were investigated with the ultimate purpose to develop a route leading to bicyclic conjugated enediones. Low-temperature, fast-quenched reactions led generally to open-chain adducts, while increase of temperature and addition of HMPA resulted in subsequent ring closure by a tandem Michael-S(N)2 process. The stereochemical features of the bicyclo[3.3.0]octanes 11 and 12, bicyclo[4.3.0]nonanes 18 and 19, bicyclo[5.3.0]decanes 22 and 23, and bicyclo[6.3.0]-undecanes 26-28 thus obtained have been determined. Ozonolysis and silica-induced elimination of the tertiary phenylsulfonyl group converted stereoselectively the above products into the desired enediones: pentalenedione 29, indenedione 30, azulenedione 32 and cyclopentacyclooctenedione 33, respectively.

  DOI：

  10.1021/jo00121a035