5'-(1,5-dimethyl-4-hexenylidene)-1',3'-cyclopentadiene | 64243-15-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 5'-(1,5-dimethyl-4-hexenylidene)-1',3'-cyclopentadiene
• 英文别名: (C5H4)=CMe(CH2CH2CH=CMe2)；1,3-Cyclopentadiene, 5-(1,5-dimethyl-4-hexenylidene)-；5-(6-methylhept-5-en-2-ylidene)cyclopenta-1,3-diene
• CAS: 64243-15-8
• 化学式: C₁₃H₁₈
• 分子量: 174.286
• InChiKey: VSUVAMYJGFXXJU-UHFFFAOYSA-N

物化性质

• 沸点：
  120-130 °C(Press: 12 Torr)
• 密度：
  0.902±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  5'-(1,5-dimethyl-4-hexenylidene)-1',3'-cyclopentadiene 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 pyridinium chlorochromate 作用下， 反应 99.5h， 生成 (3aα,6α,7aβ)-Hexahydro-3,7,7-trimethyl-3a,6-methano-3aH-inden-5(4H)-on
  参考文献：
  名称：

  Steinmeyer, Andreas; Schwede, Wolfgang; Bohlmann, Ferdinand, Liebigs Annalen der Chemie, 1988, p. 925 - 932

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲基-5-庚烯-2-酮 、 环戊二烯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 5'-(1,5-dimethyl-4-hexenylidene)-1',3'-cyclopentadiene
  参考文献：
  名称：

  一种高效的广Pat香醇类似物方法

  摘要：

  短的方法来三环[5.3.1.0 3,8 ]十一烷衍生物1，10，11和12和对三环[4.3.1.0 3,7 ]癸烷衍生物2，从工业上获得的中间体开始，进行说明。的化合物的1，10，11，和12，其具有广藿香醇的环系，12还表现出木香，广藿香状音符。的1个的H-NMR.光谱1，2和8 - 12进行了讨论。

  DOI：

  10.1002/hlca.19770600407

文献信息

• An Efficient Approach to Patchouli Alcohol Analogues
  作者：Ferdinand Näf、René Decorzant、Walter Thommen

  DOI：10.1002/hlca.19770600407

  日期：1977.6.1

  A short approach to the tricyclo [5.3.1.03,8] undecane derivatives 1, 10, 11 and 12 and to the tricyclo [4.3.1.03,7] decane derivative 2, starting from industrially available intermediates, is described. Of the compounds 1, 10, 11, and 12, which possess the ring system of patchouli alcohol, 12 also exhibits a woody, patchouli-like note. The 1H-NMR.-spectra of 1, 2 and 8–12 are discussed.

  短的方法来三环[5.3.1.0 3,8 ]十一烷衍生物1，10，11和12和对三环[4.3.1.0 3,7 ]癸烷衍生物2，从工业上获得的中间体开始，进行说明。的化合物的1，10，11，和12，其具有广藿香醇的环系，12还表现出木香，广藿香状音符。的1个的H-NMR.光谱1，2和8 - 12进行了讨论。
• A novel alkenyl-substituted ansa-zirconocene complex with dual application as olefin polymerization catalyst and anticancer drug
  作者：Santiago Gómez-Ruiz、Goran N. Kaluđerović、Dorian Polo-Cerón、Valentina Tayurskaya、Sanjiv Prashar、Mariano Fajardo、Reinhard Paschke

  DOI：10.1016/j.jorganchem.2009.05.013

  日期：2009.8

  The alkenyl substituted fulvene compound, (C(5)H(4))=CMe(CH(2)CH(2)CH=CMe(2)) (1), reacts with one equivalent of LiMe to give the lithium derivative LiC(5)H(4)(CMe(2)CH(2)CH(2)CH=CMe(2))} (2). The reaction of 2 with Me(2)Si(C(5)Me(4)H)Cl gave the ansa-ligand precursor Me(2)Si(C(5)Me(4)H)(C(5)H(4)(CMe(2)CH(2)CH(2)CH=CMe(2))) (3), which after the subsequent reaction with 2 equivalents of LiBun yielded the dilithium salt Li(2)Me(2)Si(C(5)Me(4))(C(5)H(3)(CMe(2)CH(2)CH(2)CH=CMe(2)))} (4). The alkenyl-substituted zirconocene complex [ZrMe(2)Si(g(5)-C(5)Me(4))(g5-C(5)H(3)(CMe(2)CH(2)CH(2)CH@ CMe2))}Cl(2)] (5) was synthesized by the equimolar reaction of 4 and ZrCl4. 5 was characterized by spectroscopic methods and by single crystal X-ray diffraction studies. The zirconocene compound 5 has been tested as a catalyst in the polymerization of ethylene at different temperatures and Al: Zr ratios, and also in the co-polymerization of ethylene and 1-octene, observing modest co-monomer incorporations. In addition, the cytotoxic activity of 5 was tested against tumour cell lines 8505C anaplastic thyroid cancer, A253 head and neck tumour, A549 lung carcinoma, A2780 ovarian cancer and DLD-1 colon carcinoma. Complex 5 showed the best cytotoxic activity on A2780 ovarian cancer (IC(50) value of 36.8 +/- 5.9 mu M). This represents the highest reported cytotoxic activity of a zirconocene complex on A2780 ovarian cancer. In addition, the cytotoxic activities of 5, have been compared with those obtained using cisplatin. (C) 2009 Elsevier B. V. All rights reserved.
• Regioselective preparation of vinylcyclopentadienes and selected cycloadditions
  作者：H. M. R. Hoffmann、Oskar Koch

  DOI：10.1021/jo00365a015

  日期：1986.7
• Synthese von 7-Alkyliden-tricyclo[6.3.0.02,6]undeca-4,9-dien-3,11-dionen
  作者：Axel G. Griesbeck

  DOI：10.1002/prac.19923340703

  日期：——

  The cycloaddition reaction of 6-alkyl- as well as 6,6-dialkyl substituted pentafulvenes 1a - f with 1,4-benzoquinone proceeded efficiently and highly endo-stereoselectively when water was used as the solvent. The adducts 2a - f easily underwent intramolecular photocycloaddition when irradiated in acetone or cyclohexane. The resulting trishomocubanediones 3a - f could be transformed into linearly fused tricyclopentanoids 4a - f via flash vacuum thermolysis.
• HOFFMANN H. M. R.; KOCH O., J. ORG. CHEM., 51,(1986) N 15, 2939-2944
  作者：HOFFMANN H. M. R.、 KOCH O.

  DOI：——

  日期：——