(E,E)-6,8-tetradecadiene | 72858-66-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (E,E)-6,8-tetradecadiene
• 英文别名: (6E,8E)-tetradeca-6,8-diene；(6E,8E)-6,8-tetradecadiene
• CAS: 72858-66-3
• 化学式: C₁₄H₂₆
• 分子量: 194.36
• InChiKey: MQFIWEBAWCLIQO-PHEQNACWSA-N

物化性质

• 沸点：
  259.5±7.0 °C(Predicted)
• 密度：
  0.787±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (E,E)-6,8-tetradecadiene 在 sodium hydroxide 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 39.0h， 生成 N-(2-hydroxy-1-phenylethyl)-3,6-dipentyl-3,6-dihydro-2H-thiopyran-2-carboxyamide
  参考文献：
  名称：

  ACAT inhibitors derived from hetero-Diels-Alder cycloadducts of thioaldehydes

  摘要：

  Acyl-CoA:cholesterol acyltransferase (ACAT) is the enzyme largely responsible for intracellular cholesterol esterification. A systemic inhibitor of ACAT is believed to be able to slow or even reverse the atherosclerotic process. Towards that goal, a series of cyclic sulfides, derived from the hetero-Diels-Alder reaction of thioaldehydes with 1,3-dienes, and bearing carboxamide substituents, were prepared and evaluated for in vitro (in several tissues and species) and ex vivo ACAT inhibition. Minor changes in subsequent structure were found to have a significant effect in optimization of the biological activity of this series of compounds. Copyright (C) 1996 The DuPont Merck Pharmaceutical Company.

  DOI：

  10.1016/0968-0896(96)00143-5
• 作为产物：
  描述：

  1-庚炔 在 sodium hydride 、 copper(l) chloride 、 magnesium bromide 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到(E,E)-6,8-tetradecadiene
  参考文献：
  名称：

  炔烃的加氢处理：（E，E）-1,3-二烯的简单合成

  摘要：

  使用NaBH 4 -MgBr 2 -Et 3 N-CuCl或NaH-MgBr 2 -CuCl试剂系统在四氢呋喃中原位制备的氢化铜（I），将末端炔烃转化为（E，E）-1,3-二烯良品率高。

  DOI：

  10.1039/c39870000495

文献信息

• Ti(OiPr)4/nBuLi: an attractive reagent system for [2+2+2] cyclotrimerisation reactions
  作者：V. A. Rassadin、E. Nicolas、Y. Six

  DOI：10.1039/c4cc02698e

  日期：——

  A convenient method for the [2+2+2] cyclotrimerisation of alkynes using Ti(OiPr)4/nBuLi is presented. Homotrimerisation of arylacetylenes proceeds within minutes with excellent regioselectivity. Moreover, the intermolecular construction of ABB heterotrimers can be achieved selectively from two different alkynes with similar electronic properties. The method is also suitable for the synthesis of pyridines.

  本文介绍了一种使用Ti(OiPr)4/nBuLi进行[2+2+2]环三聚化的便捷方法。芳基炔烃的同聚三聚在几分钟内进行，并且具有优异的区域选择性。此外，可以选择性地从两种具有相似电子特性的不同炔烃中合成ABB异聚三聚物。该方法也适用于吡啶的合成。
• A general and stereoselective synthesis of (e,e)-conjugated dienes.
  作者：R. Bloch、J. Abecassis

  DOI：10.1016/s0040-4039(00)81626-3

  日期：1983.1

  Cis-2,5-disubstituted-2,5-dihydrothiofene-1,1-dioxides, generated by a retro Diels-Alder reaction, lead with high stereoselectivity to (E,E)-1,4-disubstituted-1,3-dienes. The efficiency of this method is illustrated by the synthesis of two dienic insect sex pheromones.

  通过逆Diels-Alder反应生成的顺式2,5-二取代-2,5-二氢噻吩-1,1-二氧化物导致高立体选择性生成（E，E）-1,4-二取代-1,3-二烯。该方法的效率通过两种二齿昆虫性信息素的合成来说明。
• [3,3]-Sigmatropic Rearrangements in the Enantioselective Synthesis of (-)-Methylenolactocin
  作者：Xavier Ariza、Jordi Garcia、Natalia Fernández、Marta López、Laia Montserrat、Jordi Ortiz

  DOI：10.1055/s-2003-44351

  日期：——

  A Pd(II)-catalyzed [3,3]-sigmatropic rearrangement is used to transfer chirality from an enantio-enriched alk-3-ene-1,2-diol to a C 2 -symmetrical alk-2-ene-1,4-diol which, in turn, can be converted into a precursor of (-)-methylenolactocin through an additional [3,3]-sigmatropic rearrangement (either Johnson orthoester or Ireland-Claisen rearrangement).

  Pd(II) 催化的 [3,3]-sigmatropic 重排用于将手性从富含对映体的 alk-3-ene-1,2-二醇转移到 C 2 -对称 alk-2-ene-1， 4-二醇反过来又可以通过额外的 [3,3]-σ- 重排（约翰逊原酸酯或爱尔兰-克莱森重排）转化为 (-)-亚甲基内酯的前体。
• Nickel-Catalyzed Electrochemical Couplings of Vinyl Halides:  Synthetic and Stereochemical Aspects
  作者：C. Cannes、S. Condon、M. Durandetti、J. Périchon、J.-Y. Nédélec

  DOI：10.1021/jo000182f

  日期：2000.7.1

  Homo- and cross-coupling involving alkenyl halides have been performed efficiently using an electroassisted nickel-complex catalysis. Valuable product such as conjugated dienes, beta,gamma- or gamma,delta-unsaturated esters, ketones, or nitriles, as well as alkenylated aryl compounds are thus prepared with high yields and high stereoselectivity. Partial isomerization is only observed in a few cases, when the alkenyl halide is involved in a late step of the catalytic cycle. This is the case in the preparation of (Z,Z)-1,3-diene.
• Highly Stereoselective Hydrocarbation of Terminal Alkynes via Pt-Catalyzed Hydrosilylation/Pd-Catalyzed Cross-Coupling Reactions
  作者：Scott E. Denmark、Zhigang Wang

  DOI：10.1021/ol0156751

  日期：2001.4.1

  [GRAPHICS]The formal addition of an aryl-H or alkenyl-H bond across a terminal alkyne has been accomplished by the combination of platinum-catalyzed hydrosilylation followed by palladium-catalyzed cross-coupling, The use of the t-Bu3P-Pt(DVDS) catalyst in combination with tetramethyldisiloxane gave excellent regio- and stereoselectivity with a number of alkyne substrates, Subsequent, fluoride-promoted cross-coupling proceeded in high yield and stereospecificity for a variety of aryl halides.