4,4-dimethyl-5-hexenenitrile | 131922-44-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4,4-dimethyl-5-hexenenitrile
• 英文别名: 1-cyano-3,3-dimethyl-4-pentene；4,4-Dimethylhex-5-enenitrile
• CAS: 131922-44-6
• 化学式: C₈H₁₃N
• 分子量: 123.198
• InChiKey: BHDRLNDMONOPOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-5-hexenenitrile 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 生成 5,5-Dimethyl-1-pyridin-2-yl-hept-6-en-2-ol
  参考文献：
  名称：

  过渡金属催化的 1,5- 和 1,6-二烯通过碳氢键的直接裂解和加成进行分子内环化

  摘要：

  钌和铑催化的 1-(2-吡啶基)-、1-(2-咪唑基)-和 1-(2-恶唑基)-1,5-二烯的分子内 C-H/烯烃偶联反应在区域特异性方式给予 5 成员...

  DOI：

  10.1246/bcsj.71.285
• 作为产物：
  描述：

  3,3-二甲基-4-戊烯酸甲酯 在 lithium aluminium tetrahydride 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.17h， 生成 4,4-dimethyl-5-hexenenitrile
  参考文献：
  名称：

  过渡金属催化的 1,5- 和 1,6-二烯通过碳氢键的直接裂解和加成进行分子内环化

  摘要：

  钌和铑催化的 1-(2-吡啶基)-、1-(2-咪唑基)-和 1-(2-恶唑基)-1,5-二烯的分子内 C-H/烯烃偶联反应在区域特异性方式给予 5 成员...

  DOI：

  10.1246/bcsj.71.285

文献信息

• Tailor-Made Silylating Agents for Efficient Surface Modification
  作者：Philippe Schneider、Roland Cloux、Klára Fóti、Ervin sz. Kováts

  DOI：10.1055/s-1990-27084

  日期：——

  N-Silyldimethylamines are efficient silylating agents for the chemical surface modification of hydroxylated silicon dioxide preparations. The synthesis of chloro(5-X-3,3-dimethylpentyl)-dimethylsilanes and their conversion to the corresponding (dimethylamino) silanes are described, where X is a methoxy, methoxymethoxy, cyano or dimethylamino group. The bulky substituent forms a two stage protecting layer at the surface. The second stage hinders the access of nucleophiles to the silicon atom resulting an enhanced hydrolytic stability.

  N-硅基二甲基胺是对羟基二氧化硅制剂进行化学表面改性的高效硅烷化剂。本文介绍了氯(5-X-3,3-二甲基戊基)-二甲基硅烷的合成及其转化为相应的（二甲基氨基）硅烷的过程，其中 X 是甲氧基、甲氧基甲氧基、氰基或二甲基氨基。笨重的取代基在表面形成了两级保护层。第二层保护层阻碍了亲核物进入硅原子，从而提高了水解稳定性。
• Cyclizations in the homolytic reactions of unsaturated nitriles withtert-butylmercury halides in the presence of proton donors
  作者：Glen A. Russell、Ping Chen

  DOI：10.1002/(sici)1099-1395(1998100)11:10<715::aid-poc30>3.0.co;2-e

  日期：1998.10

  Cyclizations are observed in the homolytic reactions of t-BuHgI with CH2=CHCH2YCH2CN [Y = CH2, O, CMe2, C(CO2Et)(2), NCH2CN] and CH2=CHCH2CH2YCH2CN [Y = CH2, O, C(CO2Et)(2)] in Me2SO in the presence of hydriodic acid. Only with Y = C(CO2Et)(2) does the adduct radical, t-BuCH2(C) over dot HCH2YCH2CN, undergo facile 5-exo cyclization in the absence of a proton donor. The other 5-exo and all 6-exo cyclizations require substrate protonation to yield t-BuCH2CH(CH2)(n)YCH2C=NH+ (n = 1, 2), which cyclizes readily to the iminium radical cation followed by electron transfer with I- or t-BuHgI2- to form the imine as a precursor to the cyclopentanone or cyclohexanone upon hydrolysis. For CH2=CHCH2C(CO2Et)(2)CH2CN the formation of the cyclopentanone is dramatically promoted by NH4I in the dark in the absence of any other acid. In this case, where cyclization of the adduct radical occurs readily without substrate activation, protonation of the cyclized iminyl radical allows the electron transfer with I- or t-BuHgI2- to occur with regeneration of t-Bu-.. A similar effect is observed with CH2=CHCH2C(CO2Et)(2)CH2N3 where only a slow reaction is observed upon photolysis with t-BuHgI in the absence of NH4I, although apparently cyclization of t-BuCH2(C) over dot HCH2C(CO2Et)(2)CH2N3 (with loss of N-2) occurs readily. In the presence of NH4I the cyclized aminyl radical can be protonated and the resulting amine radical cation readily reduced by I- or t-BuHgI2- to continue a chain process. With the thioesters CH2=CHCH2YCH2C(O)SPh [Y = O, CH2, CMe2, C(CO2Et)(2)] significant cyclization upon photolysis with t-BuHgX occurred only for Y = C(CO2Et)(2). (C) 1998 John Wiley & Sons, Ltd.
• SCHNEIDER, PHILIPPE;CLOUX, ROLAND;FOTI, KLARA;KOVATS, ERVIN SZ., SYNTHESIS,(1990) N1, C. 1027-1031
  作者：SCHNEIDER, PHILIPPE、CLOUX, ROLAND、FOTI, KLARA、KOVATS, ERVIN SZ.

  DOI：——

  日期：——
• Transition Metal-Catalyzed Intramolecular Cyclization of 1,5- and 1,6-Dienes via Direct Cleavage and Addition of the Carbon–Hydrogen Bond
  作者：Naoaki Fujii、Fumitoshi Kakiuchi、Airi Yamada、Naoto Chatani、Shinji Murai

  DOI：10.1246/bcsj.71.285

  日期：1998.1

  Ruthenium- and rhodium-catalyzed intramolecular C–H/olefin coupling reactions of 1-(2-pyridyl)-, 1-(2-imidazolyl)-, and 1-(2-oxazolyl)-1,5-dienes proceeded in a regiospecific manner to give 5-membe...

  钌和铑催化的 1-(2-吡啶基)-、1-(2-咪唑基)-和 1-(2-恶唑基)-1,5-二烯的分子内 C-H/烯烃偶联反应在区域特异性方式给予 5 成员...