11-iodo-5-undecyne | 42049-47-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 11-iodo-5-undecyne
• 英文别名: 11-iodoundec-5-yne
• CAS: 42049-47-8
• 化学式: C₁₁H₁₉I
• 分子量: 278.176
• InChiKey: BKZZEPGDBJATQH-UHFFFAOYSA-N

物化性质

• 沸点：
  84-87 °C(Press: 0.25 Torr)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  11-iodo-5-undecyne 在 copper(l) iodide 、 联硼酸频那醇酯 、 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以36%的产率得到1-十一碳烯-6-炔
  参考文献：
  名称：

  Switchable Synthetic Strategy toward Trisubstituted and Tetrasubstituted Exocyclic Alkenes

  摘要：

  An efficient and facile method for the construction of tri- or tetrasubstituted exocyclic alkenes is achieved via a Cu(I)-catalytic system. This protocol exhibits mild conditions, low-cost catalyst, good functional group tolerance, and good yields. The selectivity toward tri- or tetrasubstituted alkenes can be delicately controlled by adjustment of base and solvent. A preliminary mechanism study manifested that the reaction undergoes a radical process, where B(2)pin(2) plays an indispensable role.

  DOI：

  10.1021/acs.orglett.8b02801
• 作为产物：
  描述：

  1,5-二碘戊烷 、 1-己炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 11-iodo-5-undecyne
  参考文献：
  名称：

  二甲基甲酰胺中碳阴极上电生成的镍（I）Salen存在下卤代炔烃的催化还原和分子内环化

  摘要：

  通过[[2,2 ' -[1,2-乙二基双（亚硝甲基））]双[苯酚基]催化还原1-碘-或1-溴-5-癸炔可以方便地制备亚萘基环戊烷，产率高达86％。] -N，N '，O，O '在包含四氟硼酸四甲基铵的二甲基甲酰胺中的碳阴极上电生成的]镍酸酯（I）。该电合成可以在卤代炔是电惰性的电势下完成，并且可以在室温下30分钟内完成。尝试在类似条件下分别由1-卤代4-壬炔和11-卤代5-十一炔合成戊二烯环丁烷和戊二烯环己烷可提供非常低的收率（分别为2％和6％）。衍生自各种卤代炔烃的其他产物是二聚体，炔烃和1-炔烃。由1-卤代4-壬炔和11-卤代5-十一炔产生的二聚体（alkadiynes）的产率为80％至89％，而icosa-5,15-diyne（由1-卤代获得的二聚体）发现-5-decyne）的收率明显较低（≤13％）。炔烃和1-炔烃的产率分别为3-10％和2-3％。提出了一种机制方案，该方案涉及由镍（

  DOI：

  10.1021/jo052007a

文献信息

• Intramolecular addition of alkyllithiums to acetylenes: Regiospecific 4-, 5-, and 6-exo-dig cyclizations
  作者：William F. Bailey、Timo V. Ovaska

  DOI：10.1016/s0040-4039(00)94585-4

  日期：1990.1

  Primary acetylenic alkyllithiums bearing a phenyl substituent on the triple bond, which may be prepared in virtually quantitative yield by low-temperature lithium-iodine interchange, undergo regiospecific exo-dig cyclization via stereoselective syn-addition of CH2Li to the carbon-carbon triple bond to give four-, five-, and six-membered carbocycles bearing an easily functionalized exocyclic lithiomethylidene

  可以通过低温锂-碘交换以几乎定量的方式制备在三键上带有苯基取代基的炔基烷基锂，并通过将CH 2 Li立体选择性合加成到碳-碳三元基团上进行区域特异性的ex-dig环化反应结合形成具有容易官能化的环外硫代亚甲基部分的四元，五元和六元碳环。类似的烷基取代的炔基烷基锂的环化限于5 -exo-dig模式。
• Cyclizations of .omega.-alkynyl halides by chromium(II) reduction
  作者：Jack K. Crandall、W. J. Michaely

  DOI：10.1021/jo00196a026

  日期：1984.11
• Cyclization of acetylenic alkyllithiums
  作者：William F. Bailey、Timo V. Ovaska

  DOI：10.1021/ja00061a006

  日期：1993.4

  The scope and limitations of cyclization reactions involving acetylenic alkyllithiums, which were prepared at -78-degrees-C by lithium-iodine exchange between the corresponding iodide and tert-butyllithium in a solution of n-pentane-diethyl ether (3:2 by volume), have been investigated. 4-Pentynyllithiums, 5-hexynyllithiums, and 6-heptynyllithiums bearing a phenyl or trimethylsilyl substituent on the triple bond undergo regiospecific exo-dig cyclization to give 4-, 5-, and 6-membered rings, respectively, bearing an exocyclic lithiomethylene moiety. Cyclization of the analogous alkyl-substituted acetylenic alkyllithiums seems to be confined to the 5-exo mode. The vinyllithium products of the cyclizations may be trapped by reaction with electrophiles to afford functionalized cycloalkylidene derivatives in good yield. The cyclization reactions were found to be highly stereoselective: intramolecular addition of the C-Li unit to the triple bond to produce 4- or 5-membered rings proceeds in a syn fashion to generate isomerically pure exocyclic vinyllithiums that may be functionalized to give stereoisomerically pure products. At the higher temperatures needed to effect cyclization of 6-heptynyllithiums, the initially formed (Z)-vinyllithium intermediate is isomerized to the more stable E-isomer which, when trapped with an electrophile, affords stereoisomerically pure product formally derived from anti addition to the triple bond.
• The reactions of ω-iodoalkynes with nickel tetracarbonyl-potassium t-butoxide
  作者：J.K. Crandall、W.J. Michaely

  DOI：10.1016/s0022-328x(00)93533-2

  日期：1973.4
• CRANDALL, J. K.;MICHAELY, W. J., J. ORG. CHEM., 1984, 49, N 22, 4244-4248
  作者：CRANDALL, J. K.、MICHAELY, W. J.

  DOI：——

  日期：——