1,5,5-trimethyl-6-(3-methyl-penta-2,4-dienylidene)-cyclohexene | 55497-46-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,5,5-trimethyl-6-(3-methyl-penta-2,4-dienylidene)-cyclohexene
• CAS: 55497-46-6；59057-11-3；63043-76-5；63043-77-6；94204-85-0
• 化学式: C₁₅H₂₂
• 分子量: 202.34
• InChiKey: BVOQGMJFUFURDX-WKXVJGGTSA-N

物化性质

• 沸点：
  280.4±7.0 °C(Predicted)
• 密度：
  0.887±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  乙烯-beta-离子醇 在 硫酸 作用下， 生成 1,5,5-trimethyl-6-(3-methyl-penta-2,4-dienylidene)-cyclohexene
  参考文献：
  名称：

  多烯的选择性官能化

  摘要：

  证明了使用硼氢化或Vilsmeyer型甲酰化选择性地官能化各种多烯的可能性。在某些情况下可以使用可逆的二氧化硫添加来保护多烯系统中的两个双键，发现与乙酸汞，硝酸th（III），溴或过乙酸的反应仅在某些情况下对选择性引入官能团有用。

  DOI：

  10.1002/hlca.19750580105

文献信息

• Convenient Synthesis of 1,3,6-Triene Systems Through Alkylation of 3-Methyl-3-sulfolene.
  作者：T. Subramanian、R. Padmakumar、Sujata V. Bhat

  DOI：10.1080/00397919708005452

  日期：1997.12

  Various 1,3,6-triene systems have been synthesised through alkylation of 3-methyl-3-sulfolene with conjugated aldehydes followed by silylation and subsequent desulfonylation. A new route to synthesis of (+/−)-α-chamigrene, isofokienol and 5-hydroxy-α-farnesene has been described.

  摘要：通过 3-甲基-3-环丁砜与共轭醛的烷基化，然后甲硅烷基化和随后的脱磺酰化，合成了各种 1,3,6-三烯体系。已经描述了合成 (+/-)-α-chamigrene、isofokienol 和 5-羟基-α-farnesene 的新途径。
• A novel regioselective synthesis of allylsilanes.
  作者：T.H. Chan、D. Labrecque

  DOI：10.1016/s0040-4039(00)92030-6

  日期：1991.2

  The anions derived from allyl sulfones were silated in the α-position. Reductive desulfonylation gave the desired allylsilanes regioselectively.

  衍生自烯丙基砜的阴离子在α位硅烷化。还原性脱磺酰化区域选择性地得到所需的烯丙基硅烷。
• Synthesis of Vitamin A via Sulfones: A C15 Sulfone Route
  作者：P. S. Manchand、M. Rosenberger、G. Saucy、P. A. Wehrli、H. Wong、L. Chambers、M. P. Ferro、W. Jackson

  DOI：10.1002/hlca.19760590207

  日期：1976.3.10

  AbstractA Synthesis of vitamin A has been achieved by alkylating a β‐ionylidene‐ethyl (C15) aromatic sulfone with 1‐acetoxy‐3‐chlormethyl‐2‐butene (C5) followed by elimination of the corresponding sulfinic acid.
• Ionic photodissociation of polyenes via a highly polarized singlet excited state
  作者：A. Mahipal Reddy、V. Jayathirtha Rao

  DOI：10.1021/jo00051a011

  日期：1992.12

  Several polyene acetates and polyene methyl ether were prepared. Upon direct excitation these polyenes undergo ionic photodissociation from their singlet excited states. Triplet-sensitization experiments on these polyenes revealed that the ionic photodissociation process is restricted to singlet excited states. The rationale put forward is that the polyene chromophore undergoes charge separation/polarization in the singlet excited state, which leads to ionic photodissociation.