cis-2-methylcyclopentyl phenyl sulfoxide | 132398-39-1

• 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: cis-2-methylcyclopentyl phenyl sulfoxide
• 英文别名: [(1R,2S)-2-methylcyclopentyl]sulfinylbenzene
• CAS: 132398-39-1；132487-06-0；132487-07-1；132487-08-2
• 化学式: C₁₂H₁₆OS
• 分子量: 208.324
• InChiKey: FCFFQQYKYBWTCD-QXQDIAAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  cis-2-methylcyclopentyl phenyl sulfoxide 在 间氯过氧苯甲酸 作用下， 以73%的产率得到(2-methylcyclopentyl)sulfonylbenzene
  参考文献：
  名称：

  Generation and intramolecular cyclization of α-sulfinyl and α-sulfonyl radicals

  摘要：

  alpha-Phenylsulfinyl and alpha-Phenylsulfonyl radicals are generated by the reactions of alpha-chlorosulfoxides and alpha-chlorosulfones with tributyltin hydride, respectively. High reaction concentration (0.2 M) is required to ensure efficient generations of these radicals. The 5-exo-type intramolecular cyclizations of these radicals are studied. The cyclization is most successful when the olefin is terminally substituted with an ester group. The sulfinyl group only induces mild diastereoselectivity on the cyclization. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00472-9
• 作为产物：
  描述：

  cis-1-methyl-2-(phenylthio)cyclopentane 在 间氯过氧苯甲酸 作用下， 以78%的产率得到cis-2-methylcyclopentyl phenyl sulfoxide
  参考文献：
  名称：

  α-磺酰基和α-亚磺酰基自由基的分子内自由基环化研究

  摘要：

  α-磺酰基和α-亚磺酰基基团可以由相应的α-卤代砜和α卤代亚砜生成。我们的结果表明，这些自由基非常有效地环化。

  DOI：

  10.1016/s0040-4039(00)98025-0

文献信息

• The study of intramolecular free radical cyclizations of α-sulfonyl and α-sulfinyl radicals
  作者：Tsai Yeun-Min、Ke Bor-Wen、Lin Chao-Hsiung

  DOI：10.1016/s0040-4039(00)98025-0

  日期：1990.1

  α-Sulfonyl and α-sulfinyl radicals can be generated from the corresponding α-halosulfones and αhalosulfoxides. Our results indicate that these radicals cyclize very efficiently.

  α-磺酰基和α-亚磺酰基基团可以由相应的α-卤代砜和α卤代亚砜生成。我们的结果表明，这些自由基非常有效地环化。
• Stereochemistry of the C−S Bond Cleavage in <i>cis</i>-2-Methylcyclopentyl Phenyl Sulfoxide Radical Cation
  作者：Enrico Baciocchi、Osvaldo Lanzalunga、Andrea Lapi、Laura Maggini

  DOI：10.1021/jo802619y

  日期：2009.2.20

  photocatalyzed oxidation of cis-2-methylcyclopentyl phenyl sulfoxide in the presence of Ag2SO4 in MeCN/H2O leads to the formation of 1-methylcyclopentanol, 1-methylcyclopentyl acetamide, and phenyl benzenethiosulfonate as the main reaction products. It is suggested that the C−S heterolysis in the radical cation is an unimolecular process leading to an ion radical pair. Fast 1,2-hydride shift in the secondary

  在MeCN / H 2 O中存在Ag 2 SO 4的情况下，TiO 2光催化氧化顺式-2-甲基环戊基苯基亚砜导致形成1-甲基环戊醇，1-甲基环戊基乙酰胺和苯基苯硫磺酸酯作为主要反应产物。建议在自由基阳离子中的CS杂解是导致离子自由基对的单分子过程。次级碳正离子中1，2-氢化物的快速移位导致1-甲基环戊基碳正离子通过与H 2 O和MeCN反应形成观察到的产物。还可能发生H 2 O对离子自由基对的攻击，但作为次要途径（<3％），会形成反式-2-甲基环戊醇。
• Generation and intramolecular cyclization of α-sulfinyl and α-sulfonyl radicals
  作者：Bor-Wen Ke、Chao-Hsiung Lin、Yeun-Min Tsai

  DOI：10.1016/s0040-4020(97)00472-9

  日期：1997.6

  alpha-Phenylsulfinyl and alpha-Phenylsulfonyl radicals are generated by the reactions of alpha-chlorosulfoxides and alpha-chlorosulfones with tributyltin hydride, respectively. High reaction concentration (0.2 M) is required to ensure efficient generations of these radicals. The 5-exo-type intramolecular cyclizations of these radicals are studied. The cyclization is most successful when the olefin is terminally substituted with an ester group. The sulfinyl group only induces mild diastereoselectivity on the cyclization. (C) 1997 Elsevier Science Ltd.