2-(phenylsulfonyl)-2-cyclopentenone | 97764-26-6

• 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-cyclopentenone
• 英文别名: 2-(Benzenesulfonyl)cyclopent-2-en-1-one
• CAS: 97764-26-6
• 化学式: C₁₁H₁₀O₃S
• 分子量: 222.265
• InChiKey: JHRQDXIMVDVZKK-UHFFFAOYSA-N

物化性质

• 沸点：
  455.5±45.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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-(phenylsulfonyl)-2-cyclopentenone 在 二甲基硫 、 臭氧 、 lithium bromide 、 lithium diisopropyl amide 作用下， 反应 4.42h， 生成 (3aS,4S,6aS)-4,6a-Bis-benzenesulfonyl-hexahydro-pentalene-1,5-dione
  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)cyclopenten-2-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以56 %的产率得到2-(phenylsulfonyl)-2-cyclopentenone
  参考文献：
  名称：

  通过 2-(苯磺酰基) 环戊二烯-2-en-1-one 的 Mukaiyama–Michael 反应制备新的手性结构单元

  摘要：

  描述了使用硫代丙酸叔丁酯的烯醇硅烷进行 2-(苯磺酰基)环戊-2-en-1-one 的高度对映和非对映选择性 Mukaiyama-Michael 反应。在化学计量条件下，产物的产率为 87%，dr 为 27:1，ee 为 91%，而在催化条件下，产率、dr 和 ee 分别为 89%、49:1 和 88% ee。还描述了 Mukaiyama–Michael 反应产物的高度立体选择性差向异构化，其产率为 77%，dr 为 22:1。由于该 Mukaiyama–Michael 反应的配体的两种对映异构体都可用，因此已经建立了一种合成该产物的所有四种立体异构体作为有用的手性结构单元的方法。

  DOI：

  10.1055/a-2030-7082

文献信息

• Enantioselective Formal Total Synthesis of Damsin
  作者：Masahisa Nakada、Ryoji Sugiyama

  DOI：10.1055/a-2017-3636

  日期：——

  Enantioselective formal total synthesis of damsin, which was isolated from Compositae Ambrosia maritima L., is described. The highly enantio- and diastereoselective catalytic Mukaiyama–Michael reaction and subsequent highly stereoselective epimerization shorten the synthetic steps. It is also reported that the enolate, which was formed by the reaction of β-keto sulfone with lithium naphthalenide, reacted

  描述了从菊科 Ambrosia maritima L.中分离出来的 damsin 的对映选择性形式全合成。高度对映和非对映选择性催化 Mukaiyama-Michael 反应和随后的高度立体选择性差向异构化缩短了合成步骤。另据报道，β-酮基砜与萘基锂反应生成的烯醇化物与氰基甲酸甲酯反应形成季立体中心，收率高，立体选择性高。这一发现扩展了从 β-酮基砜开始的合成化学。
• New synthetic methods. Conjugate addition of alkyl groups to electron deficient olefins with nitroalkanes as alkyl anion equivalents
  作者：Noboru Ono、Akio Kamimura、Hideyoshi Miyake、Isami Hamamoto、Aritsune Kaji

  DOI：10.1021/jo00220a003

  日期：1985.10
• ONO, NOBORU;KAMIMURA, AKIO;MIYAKE, HIDEYOSHI;HAMAMOTO, ISAMI;KAJI, ARITSU+, J. ORG. CHEM., 1985, 50, N 20, 3692-3698
  作者：ONO, NOBORU、KAMIMURA, AKIO、MIYAKE, HIDEYOSHI、HAMAMOTO, ISAMI、KAJI, ARITSU+

  DOI：——

  日期：——
• Cyclopentannulations leading to the synthesis of bicyclic conjugated enediones.
  作者：Tamar Yechezkel、Eugene Ghera、Daryl Ostercamp、Alfred Hassner

  DOI：10.1021/jo00121a035

  日期：1995.8

  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.
• Preparation of New Chiral Building Blocks by a Mukaiyama–Michael Reaction of 2-(Phenylsulfonyl)cyclopent-2-en-1-one
  作者：Masahisa Nakada、Ryoji Sugiyama

  DOI：10.1055/a-2030-7082

  日期：——

  proceeds in 77% yield with a dr of 22:1 is also described. Because both enantiomers of the ligand for this Mukaiyama–Michael reaction are available, a method for the synthesis of all four stereoisomers of the product as useful chiral building blocks has been established.

  描述了使用硫代丙酸叔丁酯的烯醇硅烷进行 2-(苯磺酰基)环戊-2-en-1-one 的高度对映和非对映选择性 Mukaiyama-Michael 反应。在化学计量条件下，产物的产率为 87%，dr 为 27:1，ee 为 91%，而在催化条件下，产率、dr 和 ee 分别为 89%、49:1 和 88% ee。还描述了 Mukaiyama–Michael 反应产物的高度立体选择性差向异构化，其产率为 77%，dr 为 22:1。由于该 Mukaiyama–Michael 反应的配体的两种对映异构体都可用，因此已经建立了一种合成该产物的所有四种立体异构体作为有用的手性结构单元的方法。