3-methylidene-1,7-octadiene | 68695-13-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 3-methylidene-1,7-octadiene
• 英文别名: 3-methylene-1,7-octadiene；3-methylene-octa-1,7-diene；3-Methyliden-1,7-octadien；3-Methylen-1,7-octadien；1,7-Octadiene, 3-methylene-；3-methylideneocta-1,7-diene
• CAS: 68695-13-6
• 化学式: C₉H₁₄
• 分子量: 122.21
• InChiKey: VPSGNUSPERBOFO-UHFFFAOYSA-N

物化性质

• 沸点：
  149.1±10.0 °C(Predicted)
• 密度：
  0.753±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3-methylidene-1,7-octadiene 反应 0.01h， 生成 二环[3.3.1]壬-1-烯
  参考文献：
  名称：

  应变对化学反应性的影响。MCPBA环氧化中扭转扭曲双键的相对反应性

  摘要：

  测量了MCPBA在CH 2 Cl 2 中环氧化一系列环烯烃（包括桥头烯烃和反式环烯烃）的二级反应速率。正如预期的那样，应变桥头烯烃和反式环烯烃比未应变的顺式环烯烃表现出更快的反应速率。计算烯烃、烷烃及其相应环氧化物的 MM-2 空间能以评估每个反应中释放的应变能 (ΔSE)。log k rel 与烯烃菌株的图没有显示出良好的相关性

  DOI：

  10.1021/ja00034a042
• 作为产物：
  描述：

  1-Acetoxybicyclo<3.3.1>nonane 生成 3-methylidene-1,7-octadiene
  参考文献：
  名称：

  BECKER K. B.; PFLUGER R. W., TETRAHEDRON LETT., 1979, NO 39, 3713-3716

  摘要：

  DOI：

文献信息

• Interaction of Acyclic Tetraenes and Trienes with Transition Metals: Organonickel Compounds
  作者：E. Dreher、B. Gabor、P. W. Jolly、C. Kopiske、C. Krueger、A. Limberg、R. Mynott

  DOI：10.1021/om00004a049

  日期：1995.4

  The tetraene 3,6-dimethylene-1,7-octadiene (DMOD) reacts with zerovalent [NiPR(3)] species to give (eta(2),eta(2)-DMOD)NiPR(3) in which the methylene group of one 1,3-diene fragment and the vinyl group of the second interact with the metal atom. This unsymmetrical complexation of the tetraene has been confirmed by X-ray diffraction for the P(OC6H4-o-Ph)(3)-stabilized derivative (space group P2(1)/c, a = 10.057(1) Angstrom, b = 36.196(1) Angstrom, c = 10.944(1) Angstrom, a = y = 90 degrees, beta = 105.76(1)degrees, Z = 4, R = 0.056, R(W) = 0.071) and is the result of the preferred coordination of a 1,6-heptadiene chain to the metal atom. The NMR spectra indicate that the molecule is fluxional with a pairwise exchange of the methylene groups and of the vinyl groups. The structure of the product formed in the presence of the bidentate ligands (Pr2P)-P-i(CH2)(n)PPr2i (n = 1, 2, 3) is dependent upon the length of the chain bridging the two P-atoms, and compounds have been isolated having the composition (eta(2),eta(2),eta(2),eta(2)-DMOD)Ni-2(Pr-2(i)- PCH2PPr2i), (eta(4),eta(4)-DMOD)[Ni((Pr2PC2H4PPr2i)-P-i)](2), and (eta(2),eta(2)-DMOD)[Ni((Pr2PC3H6PPr)-P-i(2)(i))](2). The molecular structure of the bis(diisopropylphosphino)ethane-containing compound has been established by X-ray diffraction (space group C2/c, a = 17.535(2) Angstrom, b = 24.152(1) Angstrom, c = 11.767(1) Angstrom, a = y = 90 degrees, beta = 120.65(1)degrees, Z = 4, R = 0.034, R(W) = 0.035) and confirms that the two 1,3-diene fragments of the tetraene interact with [Ni((Pr2PC2H4PPr2i)-P-i)] moieties. The trienes 3-methylene-1,6-heptadiene and 3-methylene-1,7-octadiene react with [NiPPr3i] species to give (eta(2),eta(2)-triene)NiPPr3i compounds in which a 1,6-heptadiene chain is complexed to the metal atom.
• Interaction of Acyclic Tetraenes and Trienes with Transition Metals: Organoiron Compounds
  作者：P. W. Jolly、C. Kopiske、C. Krueger、A. Limberg

  DOI：10.1021/om00004a048

  日期：1995.4

  The tetraene 3,6-dimethylene-1,7-octadiene (DMOD) reacts with zerovalent [FePR(3)] species (prepared by reduction of FeCl2 . nTHF with active Mg in the presence of the donor ligand) to give (eta(4),eta(4) -DMOD)FePR(3) compounds. The crystal structure of the PPh(3)-stabilized derivative (space group R ($) over bar 3, a = b = c = 20.290(9) Angstrom, alpha = beta = gamma = 117.47(3)degrees, Z = 6, R = 0.048, R(W) = 0.052) confirms that the iron atom lies at the center of a square pyramid with the P atom at the apex and the two 1,3-diene fragments forming the base. That the products of the reaction of the trienes 3-methylene-1,6-heptadiene (MHD) and 3-methylene-1,7-octadiene (MOD) with zerovalent [Fe((Pr2P)-P-i(CH2)(n)PPr2i)] species (n = 1, 2, 3) contain a triene molecule bonded in an eta(2),eta(4)-manner to the metal atom has been confirmed by X-ray diffraction for (eta(2),eta(4)-MHD)Fe((Pr2PC2H4PPr2i)-P-i) (space group P2(1)/c, a = 11.831(1) Angstrom, b = 9.744(1) Angstrom, c = 20.917(2) Angstrom, beta = 104.87(1)degrees, Z = 4, R 0.042, R(W) = 0.039). Warming a red ethereal solution of (eta(2),eta(4)-MOD)Fe((Pr2PC3H6PPr2i)-P-i) to room temperature causes dissociation of the nonconjugated double bond of the triene to give the green, paramagnetic compound (eta(4)-MOD)Fe(Pr-2(i)-PC3H6PPr2i) which reacts with CO to give the yellow, diamagnetic compound (eta(4)-MOD)Fe(CO)((Pr2PC3H6PPr2i)-P-i).
• Synthese stereoselective de dienes conjugues a partir d'alcools α-alleniques
  作者：Dariouche Djahanbini、Bernard Cazes、Jacques Gore

  DOI：10.1016/s0040-4020(01)88795-0

  日期：1984.1
• Applications of the intramolecular Diels-Alder reaction to the formation of strained molecules. Synthesis of bridgehead alkenes
  作者：Kenneth J. Shea、Sean Wise、Lonnie D. Burke、Peter D. Davis、Jeffrey W. Gilman、Arthur C. Greeley

  DOI：10.1021/ja00385a027

  日期：1982.10
• Intramolecular diels-alder cycloadditions. Synthesis of substituted derivatives of bicyclo[3.n.1]bridgehead alkenes.
  作者：Kenneth J. Shea、Sean Wise

  DOI：10.1016/s0040-4039(01)87176-8

  日期：1979.1