1,3,3-Trimethyl-2-vinyl-1-cyclopentene | 117154-84-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,3,3-Trimethyl-2-vinyl-1-cyclopentene
• 英文别名: 2-Ethenyl-1,3,3-trimethylcyclopentene
• CAS: 117154-84-4
• 化学式: C₁₀H₁₆
• 分子量: 136.237
• InChiKey: LCLDRUUNGVYDNX-UHFFFAOYSA-N

物化性质

• 沸点：
  164.6±7.0 °C(Predicted)
• 密度：
  0.866±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3,3-Trimethyl-2-vinyl-1-cyclopentene 在 四(三苯基膦)钯 bromomagnesium diisopropylamide 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 100.0h， 生成 (E)-1-(trimethylsilyl)-2-(2-methylcyclohex-1-en-1-yl)ethylene
  参考文献：
  名称：

  钯催化的乙烯基三氟甲磺酸酯与有机锡烷的偶联。合成和机械研究

  摘要：

  在氯化锂或其他合适的盐的存在下，在温和的反应条件下，钯催化的乙烯基三氟甲磺酸酯与炔属、乙烯基、烯丙基和烷基锡试剂的偶联反应以高产率发生；然而，苄基和苯基锡试剂的偶联产物产率很低。使用锡或氢化硅试剂代替有机锡配对物通过三氟甲磺酸酯基团的还原裂解产生烯烃。乙烯基三氟甲磺酸酯与六甲基二锡的钯催化反应以高产率得到乙烯基锡烷。区域选择性形成的乙烯基三氟甲磺酸酯可用于生产 1,3-二烯作为区域异构偶联产物。

  DOI：

  10.1021/ja00271a037
• 作为产物：
  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

文献信息

• Palladium-catalyzed coupling of vinyl triflates with organostannanes. Synthetic and mechanistic studies
  作者：William J. Scott、J. K. Stille

  DOI：10.1021/ja00271a037

  日期：1986.5

  The palladium-catalyzed coupling reaction of vinyl triflates with acetylenic, vinyl, allyl, and alkyl tin reagents in the presence of lithium chloride or another suitable salt takes place in high yields under mild reaction conditions; however, benzyl and phenyl tin reagents give poor yield of coupled product. The utilization of a tin or silicon hydride reagent in place of the organotin partner yields

  在氯化锂或其他合适的盐的存在下，在温和的反应条件下，钯催化的乙烯基三氟甲磺酸酯与炔属、乙烯基、烯丙基和烷基锡试剂的偶联反应以高产率发生；然而，苄基和苯基锡试剂的偶联产物产率很低。使用锡或氢化硅试剂代替有机锡配对物通过三氟甲磺酸酯基团的还原裂解产生烯烃。乙烯基三氟甲磺酸酯与六甲基二锡的钯催化反应以高产率得到乙烯基锡烷。区域选择性形成的乙烯基三氟甲磺酸酯可用于生产 1,3-二烯作为区域异构偶联产物。
• 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.