(S)-(+)-5-methyl-5-(4-methylphenyl)cyclopent-2-en-1-one | 121402-69-5

• 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: (S)-(+)-5-methyl-5-(4-methylphenyl)cyclopent-2-en-1-one
• 英文别名: (+)-5-methyl-5-p-tolyl-2-cyclopenten-1-one；(S)-5-methyl-5-p-tolyl-2-cyclopenten-1-one；(5S)-5-methyl-5-(4-methylphenyl)cyclopent-2-en-1-one
• CAS: 121402-69-5
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: IRHWVHUAYRCLIM-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-(+)-5-methyl-5-(4-methylphenyl)cyclopent-2-en-1-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以89%的产率得到(-)-(S)-2-methyl-2-(4-methylphenyl)cyclopentanone
  参考文献：
  名称：

  Okano, Kouji; Suemune, Hiroshi; Sakai, Kiyoshi, Chemical and pharmaceutical bulletin, 1988, vol. 36, p. 1379 - 1385

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,2R,6S,7R)-4-methyltricyclo[5.2.1.02,6]dec-8-en-3-one 在 吡啶 、 亚膦酸 、 sodium nitrite 作用下， 以 various solvent(s) 为溶剂， 生成 (S)-(+)-5-methyl-5-(4-methylphenyl)cyclopent-2-en-1-one
  参考文献：
  名称：

  环戊烯倍半萜，（-）-香波烯，（+）-β-cuparenone，（-）-去溴皂苷和（-）-aplysin的对映体控制合成

  摘要：

  戊烯倍半萜烯，（-）-香bert烯，（+）-cuparenone，（-）-十apaplysin和（-）-aplysin的对映体控制合成是通过在不存在非条件下采用Fischer吲哚化反应从旋光性三环二烯酮开始实现的-酸性条件为关键步骤。

  DOI：

  10.1016/s0040-4039(00)74123-2

文献信息

• Asymmetric construction of quaternary carbons from chiral malonates: selective and versatile total syntheses of the enantiomers of .alpha.- and .beta.-cuparenones from a common optically active precursor.
  作者：Jean Louis Canet、Antoine Fadel、Jacques Salaun

  DOI：10.1021/jo00038a041

  日期：1992.6

  From a single chiron (R)-4, available with high enantiomeric purity (96%) by simple enzymatic hydrolysis (PLE) of a prochiral malonate, were prepared convenient precursors of the two enantiomers of alpha- and beta-cuparenones (1a,b and 2a,b). This versatile method also allows preparations of the enantiomer (S)-4 and dimethyl 2-methyl-2-p-tolylsuccinate ((S)-9a), as well as the new butyrolactones (R)-15, (R)-23, and (S)-25, the new but-3-enolide (S)-32, and cyclopentenones (S)-22 and (S)-30, all these compounds bearing an asymmetric quaternary carbon.
• Asaoka, Morio; Hayashibe, Satoshi; Sonoda, Syuzo, Tetrahedron Letters, 1990, vol. 31, # 33, p. 4761 - 4764
  作者：Asaoka, Morio、Hayashibe, Satoshi、Sonoda, Syuzo、Takei, Hisashi

  DOI：——

  日期：——
• Lewis acid-induced reaction of silicon-containing stannyl ketones and its application to the synthesis of (+)-β-cuparenone
  作者：Tadashi Sato、Masahito Hayashi、Toshihiro Hayata

  DOI：10.1016/s0040-4020(01)92189-1

  日期：——

  Lewis acids activated only stannyl group in the silicon-containing stannyl keytones. The silyl group neither participated in the reaction directly, nor exerted any influences upon the reaction mode of the stannyl group. The reaction was applied for the synthesis of (+)-beta-cuparenone.
• ASAOKA, MORIO;HAYASHIBE, SATOSHI;SONODA, SYUZO;TAKEI, HISASHI, TETRAHEDRON LETT., 31,(1990) N3, C. 4761-4764
  作者：ASAOKA, MORIO、HAYASHIBE, SATOSHI、SONODA, SYUZO、TAKEI, HISASHI

  DOI：——

  日期：——
• OKANO, KOUJI;SUEMUNE, HIROSHI;SAKAI, KIYOSHI, CHEM. AND PHARM. BULL., 36,(1988) N 4, 1379-1385
  作者：OKANO, KOUJI、SUEMUNE, HIROSHI、SAKAI, KIYOSHI

  DOI：——

  日期：——