non-1-en-8-yne | 66031-49-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: non-1-en-8-yne
• CAS: 66031-49-0
• 化学式: C₉H₁₄
• mdl: MFCD07780413
• 分子量: 122.21
• InChiKey: HWLAICZKIKQMDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.555
• 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：

  non-1-en-8-yne 在 Pd-BaSO₄ 氢气 作用下， 以 正己烷 为溶剂， 反应 7.0h， 生成 (Z,Z,Z)-十七-1,8,11,14-四烯
  参考文献：
  名称：

  Isolation and Total synthesis of the major constituent of the roots ofcentaurea incana : aplotaxene

  摘要：

  The major constituent of the petroleum ether extract of the root of Centaurea incana was identified as (8Z, 11Z, 14Z)-1,8,11,14-heptadecatetraene (Aplotaxene 1). A convergent and highly stereoselective synthesis of this compound is reported.

  DOI：

  10.1016/s0040-4039(00)97313-1
• 作为产物：
  描述：

  1,8-壬二炔 在 Pd-BaSO₄ 喹啉 、 氢气 作用下， 以 乙醇 为溶剂， 生成 non-1-en-8-yne
  参考文献：
  名称：

  Cirsium dipsacolepis 的八种脂肪醛及其立体选择性合成

  摘要：

  摘要 已经从 Cirsium dipsacolepis 的根中分离出两种新的和六种已知的脂肪醛，即。7-辛烯醛、(2 E )-2,8-壬二烯醛、(2 E )-2,9-癸二烯醛、(2 E )-2,10-十一烯醛、(2 E ,4 E )-2,4,10 -十一碳三烯醛、(2 E ,4 E )-2,4,11-十二碳三烯醛、(2 Z ,4 Z )-2,4,11-十二碳三烯醛和 (2 E ,4 Z )-2,4,11-十二碳三烯醛. 从烷烃-α,ω-二炔中立体选择性地鉴定和合成醛。

  DOI：

  10.1016/s0031-9422(00)81427-2

文献信息

• Palladium(0)-catalyzed thioboration of terminal alkynes with 9-(alkylthio)-9-borabicyclo[3.3.1]nonane derivatives: stereoselective synthesis of vinyl sulfides via the thioboration-cross-coupling sequence
  作者：Tatsuo Ishiyama、Kohichi Nishijima、Norio Miyaura、Akira Suzuki

  DOI：10.1021/ja00069a020

  日期：1993.8

  The addition of 9-(alkylthio)-9-borabicyclo[3.3.1]nonanes (9-(RS)-9-BBN) 1 to terminal alkynes was catalyzed by Pd(PPh 3 ) 4 3 mol %) to produce 9-[(Z)-2-(alkylthio)-1-alkenyl]-9-BBN derivatives 2 in high yields. The reactions were highly regio- and stereoselective, and their conditions were sufficiently mild that a variety of functionalized alkenylboranes 2 with defined stereochemistry were readily

  9-(烷硫基)-9-硼双环[3.3.1]壬烷(9-(RS)-9-BBN) 1 加成到末端炔烃由Pd(PPh 3 ) 4 3 mol %)催化产生9- [(Z)-2-(烷硫基)-1-烯基]-9-BBN 衍生物 2 的收率很高。这些反应具有高度的区域选择性和立体选择性，并且它们的条件足够温和，可以很容易地合成各种具有确定立体化学的官能化烯基硼烷 2。硼烷 2 在与甲醇进行质子分解以产生硫醇与 1-炔烃、2-（烷硫基）-1-烯烃 3 的马尔科夫尼科夫加合物时表现出异常高的反应性。本反应的合成效用由区域选择性和立体选择性反应证明-通过钯催化的硫代硼化-交叉偶联序列合成烯基硫化物 7
• Selective iron-catalyzed transfer hydrogenation of terminal alkynes
  作者：Gerrit Wienhöfer、Felix A. Westerhaus、Rajenahally V. Jagadeesh、Kathrin Junge、Henrik Junge、Matthias Beller

  DOI：10.1039/c2cc31091k

  日期：——

  A novel iron-catalyzed transfer hydrogenation of alkynes to the corresponding alkenes applying formic acid as a hydrogen donor is reported. An in situ combination of Fe(BF4)2·6H2O and tetraphos allows for highly selective hydrogenation of a broad range of aromatic and aliphatic alkynes tolerating different functional groups.

  报道了一种新型的铁催化转移氢化反应，将炔烃转化为相应的烯烃，使用甲酸作为氢供体。现场结合Fe(BF4)2·6H2O和四磷化物，实现了对广泛的芳香和脂肪族炔烃的高度选择性氢化，耐受多种官能团。
• Controlled Nucleation of DNA Metallization
  作者：Christian T. Wirges、Jan Timper、Monika Fischler、Alla S. Sologubenko、Joachim Mayer、Ulrich Simon、Thomas Carell

  DOI：10.1002/anie.200803123

  日期：2009.1

  Silver‐plated DNA: The deposit of a thin metal layer on biomolecules, such as DNA, requires the formation of small, “magic‐sized” metal nuclei. Through the careful design of a reducing chemical functionality in the form of a dialdehyde, the nucleation process and thus the metallization step can be controlled (see scheme).

  镀银的DNA：在生物分子（例如DNA）上沉积一层薄的金属层，需要形成小的“魔术大小”的金属核。通过精心设计二醛形式的还原化学官能团，可以控制成核过程，从而控制金属化步骤（参见方案）。
• Thermal rearrangements of cyclic allenes retro-ene reactions
  作者：John D. Price、Richard P. Johnson

  DOI：10.1016/s0040-4039(00)98820-8

  日期：1985.1

  Flow vacuum thermolysis (500–650°) of 1,2-cyclonona- and 1,2-cyclodecadienes yields, as primary products, terminal enynes and enedienes. Secondary intramolecular Diels-Alder reactions of the enedienes afford cis and trans bicyclics.

  1，2-环壬二烯和1，2-环癸二烯的流式真空热解（500-650°）作为主要产物终端烯和烯二烯。烯二烯的二次分子内Diels-Alder反应产生顺式和反式双环。
• Experimental Determination of the Activation Parameters and Stereoselectivities of the Intramolecular Diels−Alder Reactions of 1,3,8-Nonatriene, 1,3,9-Decatriene, and 1,3,10-Undecatriene and Transition State Modeling with the Monte Carlo-Jumping Between Wells/Molecular Dynamics Method
  作者：Matthias K. Diedrich、Frank-Gerrit Klärner、Brett R. Beno、K. N. Houk、Hanoch Senderowitz、W. Clark Still

  DOI：10.1021/ja9643331

  日期：1997.10.1

  Experimental activation parameters for the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene have been measured, and the Monte Carlo-Jumping between Wells/Stochastic Dynamics [MC(JBW)/SD] method, which gives relative free energies of activation, was tested as a means to predict stereoselectivities. The predictions are compared to experimental results, and to predictions from quantum and molecular mechanics methods.