(S)-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenone | 151951-76-7

• 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: (S)-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenone
• 英文别名: 2-[(S)-[2,4,6-tri(propan-2-yl)phenyl]sulfinyl]cyclopent-2-en-1-one
• CAS: 151951-76-7
• 化学式: C₂₀H₂₈O₂S
• 分子量: 332.507
• InChiKey: FFRBRTAAXNCOMR-HSZRJFAPSA-N

物化性质

• 沸点：
  485.9±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenone 在 二苯甲酮 作用下， 以 四氯化碳 为溶剂， 反应 3.17h， 生成 3-(hydroxymethyl)-2-cyclopentenone
  参考文献：
  名称：

  Photo-Induced Intermolecular Radicalβ-Addition to Chiralα-(Arylsulfinyl) Enones

  摘要：

  在二苯甲酮存在下，在光照射下检查了α-（芳基亚磺酰基）烯酮与具有羟基或缩醛基团的烷基的反应。在具有大芳基（例如2,4,6-三异丙基苯基或2,4,6-三甲基苯基）的2-（芳基亚磺酰基）-2-环戊烯酮的光诱导自由基反应中观察到高非对映选择性。 3-[(2,4,6-三异丙基苯基)亚磺酰基]-3-戊烯-2-酮在1,3-二氧戊环中的光诱导反应也产生了1,3-二氧戊环-2-基的单一非对映体加合物。

  DOI：

  10.1246/bcsj.71.2957
• 作为产物：
  描述：

  6-((S)-2,4,6-Triisopropyl-benzenesulfinyl)-1,4-dioxa-spiro[4.4]non-6-ene 在 硫酸 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到(S)-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenone
  参考文献：
  名称：

  Highly Diastereoselective Intermolecular β-Addition of Alkyl Radicals to Chiral 2-(Arylsulfinyl)-2-cycloalkenones

  摘要：

  The diastereoselectivity of intermolecular beta-addition of alkyl radicals to 2-(arylsulfinyl)-acycloalkenones depends largely upon the structure of the arylsulfinyl group. The reaction of a-cyclopentenones or 2-cyclohexenones having a sterically bulky arylsulfinyl group such as (3,5-di-tert-butyl-4-methoxyphenyl)-sulfinyl, (2,4,6-triisopropylphenyl)sulfinyl or (2,4,6-trimethylphenyl)-sulfinyl group gives 3-alkyl-2-(arylsulfinyl)-1-cyclopentanones or 3-alkyl-2-(arylsulfinyl)-1-cyclohexanones in excellent yields and with high diastereoselectivity. Both the X-ray crystallographic analysis and the NOE experiment in the H-1 NMR spectrum of (S)-2-[(2,4,6-triisopropylphenyl)-sulfinyl]- and (S)-2-[(2,4,6-trimethylphenyl)sulfinyl]-2-cyclopentenone reveal an effective shielding of one of the olefin faces at the beta-position by o-isopropyl and o-methyl groups. The addition of bidentate Lewis acids reverses the stereoselection through chelating the intermediates to give the addition products with high diastereoselectivity.

  DOI：

  10.1021/jo971093e

文献信息

• Toru, Takeshi; Watanabe, Yoshihiko; Tsusaka, Machio, Journal of the American Chemical Society, 1993, vol. 115, # 22, p. 10464 - 10465
  作者：Toru, Takeshi、Watanabe, Yoshihiko、Tsusaka, Machio、Ueno, Yoshio

  DOI：——

  日期：——
• Highly Diastereoselective Intermolecular β-Addition of Alkyl Radicals to Chiral 2-(Arylsulfinyl)-2-cycloalkenones
  作者：Nobuyuki Mase、Yoshihiko Watanabe、Yoshio Ueno、Takeshi Toru

  DOI：10.1021/jo971093e

  日期：1997.10.1

  The diastereoselectivity of intermolecular beta-addition of alkyl radicals to 2-(arylsulfinyl)-acycloalkenones depends largely upon the structure of the arylsulfinyl group. The reaction of a-cyclopentenones or 2-cyclohexenones having a sterically bulky arylsulfinyl group such as (3,5-di-tert-butyl-4-methoxyphenyl)-sulfinyl, (2,4,6-triisopropylphenyl)sulfinyl or (2,4,6-trimethylphenyl)-sulfinyl group gives 3-alkyl-2-(arylsulfinyl)-1-cyclopentanones or 3-alkyl-2-(arylsulfinyl)-1-cyclohexanones in excellent yields and with high diastereoselectivity. Both the X-ray crystallographic analysis and the NOE experiment in the H-1 NMR spectrum of (S)-2-[(2,4,6-triisopropylphenyl)-sulfinyl]- and (S)-2-[(2,4,6-trimethylphenyl)sulfinyl]-2-cyclopentenone reveal an effective shielding of one of the olefin faces at the beta-position by o-isopropyl and o-methyl groups. The addition of bidentate Lewis acids reverses the stereoselection through chelating the intermediates to give the addition products with high diastereoselectivity.
• Photo-Induced Intermolecular Radical<i>β</i>-Addition to Chiral<i>α</i>-(Arylsulfinyl) Enones
  作者：Nobuyuki Mase、Yoshihiko Watanabe、Takeshi Toru

  DOI：10.1246/bcsj.71.2957

  日期：1998.12

  The reactions of α-(arylsulfinyl) enones with alkyl radicals having a hydroxy or acetal group were examined under photo-irradiation in the presence of benzophenone. High diastereoselectivity was observed in the photo-induced radical reaction of 2-(arylsulfinyl)-2-cyclopentenones having a bulky aryl group, such as the 2,4,6-triisopropylphenyl or 2,4,6-trimethylphenyl group. The photo-induced reaction of 3-[(2,4,6-triisopropylphenyl)sulfinyl]-3-pentene-2-one in 1,3-dioxolane also gave a single diastereomer of the 1,3-dioxolan-2-yl adduct.

  在二苯甲酮存在下，在光照射下检查了α-（芳基亚磺酰基）烯酮与具有羟基或缩醛基团的烷基的反应。在具有大芳基（例如2,4,6-三异丙基苯基或2,4,6-三甲基苯基）的2-（芳基亚磺酰基）-2-环戊烯酮的光诱导自由基反应中观察到高非对映选择性。 3-[(2,4,6-三异丙基苯基)亚磺酰基]-3-戊烯-2-酮在1,3-二氧戊环中的光诱导反应也产生了1,3-二氧戊环-2-基的单一非对映体加合物。