1,2,3,3,4,4-Hexamethylcyclopentene | 79816-97-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,2,3,3,4,4-Hexamethylcyclopentene
• CAS: 79816-97-0
• 化学式: C₁₁H₂₀
• 分子量: 152.28
• InChiKey: YJCTXJODKYYCQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  1,2,3,3,4,4-Hexamethylcyclopentene 在 氧气 、 tetraphenylporphyrin 、 碳酸氢钠 、 iron(II) sulfate 、 copper dichloride 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.75h， 生成 2-methylene-1,3,3,4,4-pentamethylcyclopentanol
  参考文献：
  名称：

  Reaction of Highly Methylated 2-Methylenecycloalkyl Hydroperoxides with FeSO₄/CuCl₂. Remarkably Efficient 5-endo-trig or 6-endo-trig Cyclization of the Intermediate Carbon Radicals

  摘要：

  Treatment of 1,3,3 4,4,5,5-heptamethyl-2-methylenecyclopentyl hydroperoxide, derived from a singlet oxygen ene reaction of 1,2,3,3,4,4,5,5-octamethylcyclopentene, with FeSO4/CuCl2 gave 1-chloro-2,2,3,3,4,4-hexamethylcyclopentyl methyl ketone in high yield, suggesting that the consecutive O-O and C-C bond fission is followed by a novel 5-endo-trig cyclization of the intermediate carbon radical to the activated C-C double bond. In the case of 1,3,3,6,6-pentamethyl-2-methylene-1-cyclohexyl hydroperoxide also, an efficient 6-endo-trig cyclization of the corresponding carbon radical was realized giving 1-chloro-2,2,5,5-tetramethylcyclohexyl methyl ketone in high yield.

  DOI：

  10.1021/jo990127a
• 作为产物：
  描述：

  4-chloro-2,3-dimethyl-2-pentene 、 异丁烯 在 盐酸 、 zinc chloride diethyl ether 作用下， 生成 1,2,3,3,4,4-Hexamethylcyclopentene 、 1,2,3,3,5,5-Hexamethylcyclopenten
  参考文献：
  名称：

  Klein, Herbert; Mayr, Herbert, Angewandte Chemie, 1981, vol. 93, # 12, p. 1069 - 1070

  摘要：

  DOI：

文献信息

• Exceptionally Stable Ozonides. Influence of Methyl Substituents on the Course of Cyclopentene Ozonolyses and on the Reactivities of Ozonides
  作者：Herbert Mayr、Janusz Baran、Elfriede Will、Hideyuki Yamakoshi、Koichi Teshima、Masatomo Nojima

  DOI：10.1021/jo00096a059

  日期：1994.8

  Ozonolyses of 1,2,3,3,4,4,5,5-octamethyl- (1a), 1,2,3,3,4,4,5-heptamethyl- (1b), and 1,2,3,3,4,4-hexamethyl cyclopentenes (1c) in methanol did not yield the ordinary hemiperacetals but gave the corresponding ozonides 6a-c instead. The ozonides 6a,b were extremely stable nd remained intact even when refluxed with triphenylphosphine in tetrahydrofuran. Cycloreversion of the primary ozonides from unsymmetrically substituted 1,2,3,3-tetramethylcyclopentene (1d) and 1,5,5-trimethylcyclopentene (1g) was highly regioselective to yield the intermediate omega-oxo carbonyl oxides with the geminal methyl groups remote from the carbonyl oxide groups.
• Mayr Herbert, Baran Janusz, Will Elfriede, Yamakoshi Hideyuki, Teshima Ko+, J. Org. Chem, 59 (1994) N 17, S 5055- 5058
  作者：Mayr Herbert, Baran Janusz, Will Elfriede, Yamakoshi Hideyuki, Teshima Ko+

  DOI：——

  日期：——
• Klein, Herbert; Mayr, Herbert, Angewandte Chemie, 1981, vol. 93, # 12, p. 1069 - 1070
  作者：Klein, Herbert、Mayr, Herbert

  DOI：——

  日期：——
• Reaction of Highly Methylated 2-Methylenecycloalkyl Hydroperoxides with FeSO₄/CuCl₂. Remarkably Efficient 5-<i>e</i><i>ndo</i>-<i>t</i><i>rig</i> or 6-<i>e</i><i>ndo</i>-<i>t</i><i>rig </i>Cyclization of the Intermediate Carbon Radicals
  作者：Yuji Nonami、Janusz Baran、Jacek Sosnicki、Herbert Mayr、Araki Masuyama、Masatomo Nojima

  DOI：10.1021/jo990127a

  日期：1999.5.1

  Treatment of 1,3,3 4,4,5,5-heptamethyl-2-methylenecyclopentyl hydroperoxide, derived from a singlet oxygen ene reaction of 1,2,3,3,4,4,5,5-octamethylcyclopentene, with FeSO4/CuCl2 gave 1-chloro-2,2,3,3,4,4-hexamethylcyclopentyl methyl ketone in high yield, suggesting that the consecutive O-O and C-C bond fission is followed by a novel 5-endo-trig cyclization of the intermediate carbon radical to the activated C-C double bond. In the case of 1,3,3,6,6-pentamethyl-2-methylene-1-cyclohexyl hydroperoxide also, an efficient 6-endo-trig cyclization of the corresponding carbon radical was realized giving 1-chloro-2,2,5,5-tetramethylcyclohexyl methyl ketone in high yield.