1-Acetyl-2,2,5-trimethylcyclopent-5-ene | 125952-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Acetyl-2,2,5-trimethylcyclopent-5-ene
• 英文别名: 1-acetyl-2,2,5-trimethylcyclopent-1-ene；1-(2,5,5-Trimethylcyclopenten-1-yl)ethanone
• CAS: 125952-10-5
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: HLAVHVYCRZRWTB-UHFFFAOYSA-N

物化性质

• 沸点：
  211.9±19.0 °C(Predicted)
• 密度：
  0.908±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  1-Acetyl-2,2,5-trimethylcyclopent-5-ene 在 sodium methylate 作用下， 以 乙醇 、 正戊烷 为溶剂， 反应 14.83h， 生成 1,3,3-Trimethyl-2-vinyl-1-cyclopentene
  参考文献：
  名称：

  Reactions of methyl(2,5,5-trimethyl-l-cyclopenten-l-yl)carbene and the photochemistry of 2-(1-propynyl)-2,5,5-trimethylcyclopentanone

  摘要：

  Dienes 7 and 8 are formed both on photolysis of 1 and on triplet decomposition of diazo compound 14. These observations appear to imply that biradical 3, a photochemical intermediate formed from 1, closes to carbene 9, from which 7 and 8 result on migration of hydrogen. It is shown, however, that dienes 7 and 8 are secondary products formed both on photolysis of 1 and on decomposition of 14. Photodimer 28 is also formed on irradiation of 1, and it is suggested that 28 arises by 1,3 acyl shift of 1 to allenic ketone 29 followed by head-to-head dimerization of 29 at the beta,gamma double bond.

  DOI：

  10.1021/jo00076a022
• 作为产物：
  描述：

  2,5,5-trimethylcyclopent-1-en-1-yl triflate 在 盐酸 、 四(三苯基膦)钯 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 51.0h， 生成 1-Acetyl-2,2,5-trimethylcyclopent-5-ene
  参考文献：
  名称：

  Palladium-catalyzed coupling reactions of (.alpha.-ethoxyvinyl)trimethylstannane with vinyl and aryl triflates

  摘要：

  DOI：

  10.1021/jo00297a029

文献信息

• Synthesis of five- and six-membered 2-trimethylsilyl-1,3,3-trimethylcycloalkenes: A novel preparation of alkyl/alkenyl/aryl-(1′,3′,3′-trimethylcyclopentenyl)ketones
  作者：Venkatesha Achanna、Hariprasad Suresh

  DOI：10.2298/jsc120501015a

  日期：——

  2-Trimethylsilyl-1,3,3-trimethylcyclopentene and 2-trimethylsilyl-1,3,3-trimethylcyclohexene were prepared in good yields by the Wurtz-Fittig coupling reaction of the corresponding 2-iodo-1,3,3-trimethylcyclopentene and 2-chloro-1,3,3-trimethylcyclohexene with metallic sodium and chlorotrimethylsilane in anhydrous ether solvent. The Friedel-Crafts acylation reaction of 2-trimethylsilyl-1,3,3-trimethylcyclopentene with six different acid chlorides and the novel preparation of six alkyl/alkenyl/aryl-(1?,3?,3?-trimethylcyclopentenyl)ketones is reported.

  2-三甲基硅基-1,3,3-三甲基环戊烯和 2-三甲基硅基-1,3,3-三甲基环戊烯和 2-三甲基硅基-1,3,3-三甲基环己烯通过 和 2-三甲基硅基-1,3,3-三甲基环己烯的 Wurtz-Fittig 2-碘-1,3,3-三甲基环戊烯和 2-氯-1,3,3-三甲基环己烯的 Wurtz-Fittig 偶联反应 与金属钠和三甲基氯硅烷在无水乙醚溶剂中发生的偶联反应。 2-三甲基硅基-1-氯-1,3,3-三甲基环己烯的弗里德尔-卡夫斯酰化反应 2-三甲基硅基-1,3,3-三甲基环戊烯与六种不同酸氯化物的弗里德尔-卡夫斯酰化反应，以及六种不同酸氯化物的新型制备方法。 氯化物的弗里德尔-卡夫斯酰化反应以及六种 烷基/烯基/芳基-(1?,3?,3?-三甲基环戊烯基)酮的新制备方法。
• Palladium-catalyzed coupling reactions of (.alpha.-ethoxyvinyl)trimethylstannane with vinyl and aryl triflates
  作者：Hyok Boong Kwon、Blaine H. McKee、J. K. Stille

  DOI：10.1021/jo00297a029

  日期：1990.5
• Reactions of methyl(2,5,5-trimethyl-l-cyclopenten-l-yl)carbene and the photochemistry of 2-(1-propynyl)-2,5,5-trimethylcyclopentanone
  作者：D. Venugopal、Paul Margaretha、William C. Agosta

  DOI：10.1021/jo00076a022

  日期：1993.11

  Dienes 7 and 8 are formed both on photolysis of 1 and on triplet decomposition of diazo compound 14. These observations appear to imply that biradical 3, a photochemical intermediate formed from 1, closes to carbene 9, from which 7 and 8 result on migration of hydrogen. It is shown, however, that dienes 7 and 8 are secondary products formed both on photolysis of 1 and on decomposition of 14. Photodimer 28 is also formed on irradiation of 1, and it is suggested that 28 arises by 1,3 acyl shift of 1 to allenic ketone 29 followed by head-to-head dimerization of 29 at the beta,gamma double bond.