16碳二烯酸 | 21964-51-2

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 无环烃
• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 16碳二烯酸
• 英文名称: hexadeca-1,15-diene
• 英文别名: 1,15-hexadecadiene；1,15-hexadecadien；Hexadeca-1,15-dien；Hexadecadien-(1,15)
• CAS: 21964-51-2
• 化学式: C₁₆H₃₀
• 分子量: 222.414
• InChiKey: JEJVUMPKJVMOEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  −14-−12 °C(lit.)
• 沸点：
  142-147 °C6 mm Hg(lit.)
• 密度：
  0.789 g/mL at 20 °C(lit.)
• 闪点：
  100 °C
• 保留指数：
  1577;1581

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  16
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 安全说明：
  S23,S24/25
• WGK Germany：
  3
• 海关编码：
  2901299090

反应信息

• 作为反应物：
  描述：

  16碳二烯酸 在 氢溴酸 、 双氧水 、 diborane(6) 作用下， 以 正辛烷 为溶剂， 反应 2.0h， 生成 16-溴-1-十六烷醇
  参考文献：
  名称：

  Multiple Electron Tunneling Paths across Self-Assembled Monolayers of Alkanethiols with Attached Ruthenium(II/III) Redox Centers

  摘要：

  Alkanethiol monolayers with pendant redox centers are deposited on gold electrolytes by self-assembly. The monolayers are composed of both an electroactive thiol, HS(CH2)(n)C(O)NHCH(2)pyRu(NH3)(5)(2+/3+), with 10-15 methylene groups, and a diluent thiol, HS(CH2)mCoOH, also with 10-15 methylene groups. The monolayers are classified as ''matched'' (n = m), ''exposed'' (n = 15, m = 10-14), and ''buried'' (n = 10, m = 11-15) according to the relative position of the redox center. Cyclic voltammograms in aqueous Na2SO4 indicate that the monolayers are close-packed with the redox centers residing in the aqueous phase in all but the most buried cases. Measurements of electron transfer kinetics by several methods (cyclic voltammetry, ac impedance spectroscopy, chronoamperometry) yield an internally consistent set of kinetic parameters, the standard rate constant k degrees, and the reorganization energy lambda of the redox centers. The reorganization energies are in good agreement with the theoretically predicted value of 1.0 eV for the pyRu(NH3)(5) redox centers. Plots of ln(k degrees) vs m are linear in all three cases. The slopes of the linear regression fit provide tunneling parameters (beta, where k degrees approximate to e(-beta m)) of 0.97 +/- 0.03 (matched cases), 0.83 +/- 0.03 (exposed cases) and 0.16 +/- 0.02 (buried cases) per methylene. This pattern of beta's is interpreted in terms of electronic coupling between the redox center and the electrode via both the redox thiol and the proximate diluent thiols, with the coupling via the diluent thiols dominating in the exposed cases.

  DOI：

  10.1021/jp962831q
• 作为产物：
  描述：

  1,10-二溴癸烷 在 乙醚 、 magnesium 作用下， 生成 16碳二烯酸
  参考文献：
  名称：

  Polymerization of Higher α-Diolefins with Metal Alkyl Coordination Catalysts¹

  摘要：

  DOI：

  10.1021/ja01526a072

文献信息

• Studies on the Synthesis of Macrocyclic Allenes by Ring Closing Metathesis and Doering-Moore-Skattebøl Reaction
  作者：Christian E. Janßen、Norbert Krause

  DOI：10.1002/ejoc.200500096

  日期：2005.6

  access to the allenic cyclophane 8. The macrocycles 13 and 17 with the allenic bridge between the aromatic units were also obtained efficiently by copper-promoted S N 2'-substitution of propargylic acetates and ring-closing metathesis. Alternatively, macrocyclic allenes can be synthesized by ring-closing metathesis of α,ω-bisallenes, as was demonstrated by the formation of the products 20, 21, and 23.

  描述了几种有效的合成方法，合成具有通用结构 2/3 的丙二烯环芳烃，它们作为手性配体或宿主分子很受关注。钌催化的闭环复分解和使用 Seyferth 试剂 PhHgCBr 3 的 Doering-Moore-Skattebel (DMS) 反应的组合提供了获得丙二烯环烷 8 的直接途径。 大环 13 和 17 与芳烃单元之间的丙二烯桥还通过铜促进的 SN 2'-丙炔乙酸酯的取代和闭环复分解有效地获得。或者，大环丙二烯可以通过 α,ω-双丙二烯的闭环复分解合成，如产物 20、21 和 23 的形成所示。
• Syntheses and Palladium, Platinum, and Borane Adducts of Symmetrical Trialkylphosphines with Three Terminal Vinyl Groups, P((CH₂)_mCH=CH₂)₃
  作者：Agnieszka J. Nawara-Hultzsch、Katrin Skopek、Takanori Shima、Michał Barbasiewicz、Gisela D Hess、Dirk Skaper、John A Gladysz

  DOI：10.1515/znb-2010-0327

  日期：2010.3.1

  Reactions of Br(CH₂)_mCH=CH₂ with Mg powder and then PCl₃ (0.33 equiv.) afford P((CH₂)_m- CH=CH₂)₃ (1; m = a, 4; b, 5; c, 6; d, 7; e, 8; f, 9; 52 - 87%). Reactions of 1a - c, e with PdX₂(COD) (X = Cl, Br) give trans-PdX₂(P((CH₂)_mCH=CH₂)₃)₂ (35 - 92%). Reactions of 1b - e with PtCl₂ in benzene give mainly trans-PtCl₂(P((CH₂)mCH=CH₂)₃)₂ (trans-5b-e; 52 - 75%), whereas those with K₂PtCl₄ in water give mainly cis-5b-e (33 - 70%). The reaction of equimolar quantities of 1c and H₃B・S(CH₃)₂ gives the 1 : 1 adduct H₃B・P((CH₂)₆CH=CH₂)₃ (85%). In none of these transformations are by-products derived from the C=C linkages observed

  Br(CH₂)ₘCH=CH₂与镁粉和PCl₃（0.33当量）的反应得到P((CH₂)ₘ- CH=CH₂)₃（1; m = a, 4; b, 5; c, 6; d, 7; e, 8; f, 9; 52 - 87％）。1a - c, e与PdX₂(COD)（X = Cl, Br）反应得到反式-PdX₂(P((CH₂)ₘCH=CH₂)₃)₂（35 - 92％）。1b - e与PtCl₂在苯中反应主要得到反式-PtCl₂(P((CH₂)ₘCH=CH₂)₃)₂（反-5b-e; 52 - 75％），而与K₂PtCl₄在水中反应主要得到顺式-5b-e（33 - 70％）。1c和H₃B・S(CH₃)₂等量反应得到1：1加合物H₃B・P((CH₂)₆CH=CH₂)₃（85％）。在这些转化中，没有观察到来自C=C键的副产物。
• Enzymatic Oxidative Tandem Decarboxylation of Dioic Acids to Terminal Dienes
  作者：Alexander Dennig、Sara Kurakin、Miriam Kuhn、Andela Dordic、Mélanie Hall、Kurt Faber

  DOI：10.1002/ejoc.201600358

  日期：2016.7

  The biocatalytic oxidative tandem decarboxylation of C7–C18 dicarboxylic acids to terminal C5–C16 dienes was catalyzed by the P450 monooxygenase OleT with conversions up to 29 % for 1,11-dodecadiene (0.49 g L–1). The sequential nature of the cascade was proven by the fact that decarboxylation of intermediate C6–C11 ω-alkenoic acids and heptanedioic acid exclusively gave nonconjugated 1,4-pentadiene;

  C7-C18 二元羧酸到末端 C5-C16 二烯的生物催化氧化串联脱羧由 P450 单加氧酶 OleT 催化，1,11-十二二烯（0.49 g L-1）的转化率高达 29%。中间体 C6-C11 ω-链烯酸和庚二酸的脱羧反应仅生成非共轭 1,4-戊二烯，证明了级联的顺序性质；放大允许分离 1,15-十六二烯和 1,11-十二二烯；该系统代表了一条从可再生二元羧酸获得末端二烯的绿色短途路线。
• Casteignau,G.; Villessot,D., Bulletin de la Societe Chimique de France, 1968, p. 3893 - 3903
  作者：Casteignau,G.、Villessot,D.

  DOI：——

  日期：——
• Reformatski; Grischkewitsch-Trochimowski; Semenzow, Chemische Berichte, 1911, vol. 44, p. 1885
  作者：Reformatski、Grischkewitsch-Trochimowski、Semenzow

  DOI：——

  日期：——

表征谱图