(E)-7-tetradecen-5-yne | 100222-29-5

• 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)-7-tetradecen-5-yne
• 英文别名: tetradec-7-en-5-yne；(E)-tetradec-7-en-5-yne
• CAS: 100222-29-5
• 化学式: C₁₄H₂₄
• 分子量: 192.345
• InChiKey: GWBYBLSETVSJTQ-BUHFOSPRSA-N

物化性质

• 沸点：
  267.7±9.0 °C(Predicted)
• 密度：
  0.813±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  14
• 可旋转键数：
  7
• 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)-7-tetradecen-5-yne 、 联硼酸频那醇酯 、 碘甲烷 在 三苯基膦 、 copper(l) chloride 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 4,4,5,5-tetramethyl-2-((5Z,7E)-6-methyltetradeca-5,7-dien-5-yl)-1,3,2-dioxaborolane 、 4,4,5,5-tetramethyl-2-((5Z,7E)-5-methyltetradeca-5,7-dien-6-yl)-1,3,2-dioxaborolane
  参考文献：
  名称：

  Copper(I)-Catalyzed Formal Carboboration of Alkynes: Synthesis of Tri- and Tetrasubstituted Vinylboronates

  摘要：

  The first copper-catalyzed formal carboboration of alkynes, in which a C-B bond and a C-C bond are created in a single catalytic cycle, is presented. The reaction proceeds with high regioselectivity and syn-stereoselectivity to form tri- and tetrasubstituted vinylboronic esters from commercially available bis-(pinacolato)diboron. A subsequent cross-coupling reaction gives access to highly substituted alkenes.

  DOI：

  10.1021/ja307670k
• 作为产物：
  描述：

  2,3-dimethylbutan-2-yl-propan-2-yloxy-[(E)-tetradec-5-en-7-yn-6-yl]borane 以62%的产率得到
  参考文献：
  名称：

  BROWN, H. C.;BHAT, N. G.;BASAVAIAH, D., ISRAEL J. CHEM., 1984, 24, N 2, 72-75

  摘要：

  DOI：

文献信息

• The Synthesis of Internal Conjugated (<i>E</i>)-Enynyldialkylboranes and Their Applications to the Syntheses of Conjugated Alkynones, Conjugated (<i>E</i>)-Enynes, and Conjugated Enynes Bearing an Unsaturated Group on the Double Bond
  作者：Masayuki Hoshi、Yuzuru Masuda、Akira Arase

  DOI：10.1246/bcsj.58.1683

  日期：1985.6

  (E)-Enynyldialkylboranes, thus obtained, gave regio- and/or stereospecifically defined corresponding conjugated alkynones by alkaline hydrogen peroxide oxidation, conjugated (E)-enynes by protonolysis with acetic acid, and conjugated enynes bearing an unsaturated group on the internal alkenyl carbon atom by bis(acetylacetonato)copper-catalyzed cross-coupling reaction with allyl bromide or 1-bromo-1-hexyne respectively

  内共轭 (E)-烯基二烷基硼烷是通过 1-iodo-1-炔烃与二烷基硼烷和 1-炔基锂的连续反应合成的，产率为 31-79%。由此获得的 (E)-烯基二烷基硼烷通过碱性过氧化氢氧化产生区域和/或立体特异性定义的相应共轭炔酮，通过用乙酸质子分解产生共轭 (E)-烯炔，以及在内部烯基碳上带有不饱和基团的共轭烯炔原子通过双（乙酰丙酮）铜催化的交叉偶联反应分别与烯丙基溴或 1-溴-1-己炔。
• Preparation of polyfunctional diorganomercurials and their transmetallation to diorganozincs. Applications to the preparation of optically active secon
  作者：Michael J. Rozema、Duddu Rajagopal、Charles E. Tucker、Paul Knochel

  DOI：10.1016/0022-328x(92)88002-z

  日期：1992.10

  Two new methods of preparation of functionalized diorganomercurials have been developed. The first method involves a substitution reaction of (ICH2)2Hg with zinc-copper reagents FG-RCu(CN)ZnI in THF/DMF at - 60-degrees-C. Functional groups such as an ester, nitrile, ketone, phosphonate, halide, and boronic ester are tolerated in this reaction. The second method involves a reductive transmetallation between polyfunctional organozinc halides and mercurous chloride (Hg2Cl2). This very convenient procedure provides a rapid route to various functionalized diorganomercurials in good yields (61-89% yield). The synthetic utility of these mercury organometallics is demonstrated. Their transmetallation with zinc dust (toluene, 80-degrees-C, 3-5 h) affords dialkylzincs which add enantioselectively to aldehydes in the presence of a catalytic amount (20 mol%) of the norephedrine derivative 13. This transmetallation can also be used to prepare stereoselectively (E)-alkenylzinc halides (> 98% E). Addition of Cl(H)ZrCp2 to (E)-5-chloropentenylzinc bromide in CH2Cl2 (25-degrees-C, 1 min) affords a 1,1-bimetallic of zinc and zirconium Cl(CH2)4CH(ZnBr)ZrCp2(Cl) which reacts stereoselectively with an aldehyde providing the (E)-disubstituted olefin (49% yield; 100% E).
• HOSHI, MASAYUKI;MASUDA, YUZURU;ARASE, AKIRA, BULL. CHEM. SOC. JAP., 1985, 58, N 6, 1683-1689
  作者：HOSHI, MASAYUKI、MASUDA, YUZURU、ARASE, AKIRA

  DOI：——

  日期：——
• Copper(I)-Catalyzed Formal Carboboration of Alkynes: Synthesis of Tri- and Tetrasubstituted Vinylboronates
  作者：Ricardo Alfaro、Alejandro Parra、José Alemán、José Luis García Ruano、Mariola Tortosa

  DOI：10.1021/ja307670k

  日期：2012.9.19

  The first copper-catalyzed formal carboboration of alkynes, in which a C-B bond and a C-C bond are created in a single catalytic cycle, is presented. The reaction proceeds with high regioselectivity and syn-stereoselectivity to form tri- and tetrasubstituted vinylboronic esters from commercially available bis-(pinacolato)diboron. A subsequent cross-coupling reaction gives access to highly substituted alkenes.
• BROWN, H. C.;BHAT, N. G.;BASAVAIAH, D., ISRAEL J. CHEM., 1984, 24, N 2, 72-75
  作者：BROWN, H. C.、BHAT, N. G.、BASAVAIAH, D.

  DOI：——

  日期：——