3-(4-甲基苯基)硫烷基-3-苯基-2-苯并呋喃-1-酮 | 61613-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 3-(4-甲基苯基)硫烷基-3-苯基-2-苯并呋喃-1-酮
• 英文名称: 3-phenyl-3-p-tolylsulfanyl-3H-isobenzofuran-1-one
• 英文别名: 1(3H)-Isobenzofuranone, 3-[(4-methylphenyl)thio]-3-phenyl-；3-(4-methylphenyl)sulfanyl-3-phenyl-2-benzofuran-1-one
• CAS: 61613-18-1
• 化学式: C₂₁H₁₆O₂S
• 分子量: 332.423
• InChiKey: WWDRNMORZGROAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  S-(4-methylphenyl) 2-benzoylbenzenecarbothioate 以 neat (no solvent) 为溶剂， 反应 6.0h， 以89%的产率得到3-(4-甲基苯基)硫烷基-3-苯基-2-苯并呋喃-1-酮
  参考文献：
  名称：

  Solid-State Photochemistry of o-Aroylbenzothioates:  Absolute Asymmetric Phthalide Formation Involving 1,4-Aryl Migration

  摘要：

  Solid-state photoreactions of S-(o-tolyl), S-phenyl, and S-(m-tolyl) 2-benzoylbenzothioates, which formed chiral crystals by spontaneous resolution, underwent an unprecedented intramolecular cyclization involving phenyl migration to afford optically active corresponding 3-phenyl-3-(arylthio)phthalide in good chemo- and enantioselectivities. Stereochemical assignment and substituent probe experiment of this photoreaction sequence led to a reliable conclusion that this reaction was rationalized on the basis of the aryl migration rather than the well-recognized radicalic mechanism. Furthermore, the chirality preservation in the crystals was demonstrated by means of the bisignated CD spectra, which allowed assignment of the origin of the specific CD band and the helicity of the chiral molecules.

  DOI：

  10.1021/ja982696q

文献信息

• Takahashi, Masaki; Fujita, Tsutomu; Watanabe, Shoji, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 3, p. 487 - 491
  作者：Takahashi, Masaki、Fujita, Tsutomu、Watanabe, Shoji、Sakamoto, Masami

  DOI：——

  日期：——
• Solid-State Photochemistry of <i>o</i>-Aroylbenzothioates:  Absolute Asymmetric Phthalide Formation Involving 1,4-Aryl Migration
  作者：Masaki Takahashi、Norio Sekine、Tsutomu Fujita、Shoji Watanabe、Kentaro Yamaguchi、Masami Sakamoto

  DOI：10.1021/ja982696q

  日期：1998.12.1

  Solid-state photoreactions of S-(o-tolyl), S-phenyl, and S-(m-tolyl) 2-benzoylbenzothioates, which formed chiral crystals by spontaneous resolution, underwent an unprecedented intramolecular cyclization involving phenyl migration to afford optically active corresponding 3-phenyl-3-(arylthio)phthalide in good chemo- and enantioselectivities. Stereochemical assignment and substituent probe experiment of this photoreaction sequence led to a reliable conclusion that this reaction was rationalized on the basis of the aryl migration rather than the well-recognized radicalic mechanism. Furthermore, the chirality preservation in the crystals was demonstrated by means of the bisignated CD spectra, which allowed assignment of the origin of the specific CD band and the helicity of the chiral molecules.