6-­acetyl 2-­naphthonitrile | 116611-96-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-­acetyl 2-­naphthonitrile
• 英文别名: 2-acetyl-6-cyanonaphthalene；6-Cyan-2-acetylnaphthalin；6-acetylnaphthalene-2-carbonitrile
• CAS: 116611-96-2
• 化学式: C₁₃H₉NO
• 分子量: 195.221
• InChiKey: WVPHIMDBTVYZKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-­acetyl 2-­naphthonitrile 在 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 三乙胺 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (R)-1-(6-cyanonaphthalen-2-yl)ethyl pivalate
  参考文献：
  名称：

  Nickel-Catalyzed Cross-Couplings of Benzylic Pivalates with Arylboroxines: Stereospecific Formation of Diarylalkanes and Triarylmethanes

  摘要：

  We have developed a stereospecific nickel-catalyzed cross-coupling of benzylic pivalates with arylboroxines. The success of this reaction relies on the use of Ni(cod)(2) as the catalyst and NaOMe as a uniquely effective base. This reaction has broad scope with respect to the arylboroxine and benzylic pivalate, enabling the synthesis of a variety of diarylalkanes and triarylmethanes in good to excellent yields and ee's.

  DOI：

  10.1021/ja312087x
• 作为产物：
  描述：

  6-bromonaphthalene-2-carbonyl chloride 在 ammonium hydroxide 、 1,3-双(二苯基膦)丙烷 、 palladium diacetate 、 trimethyl-ammonium tetrafluoroborate 、 三乙胺 、 三氯乙酰氯 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 6-­acetyl 2-­naphthonitrile
  参考文献：
  名称：

  Nickel-Catalyzed Cross-Couplings of Benzylic Pivalates with Arylboroxines: Stereospecific Formation of Diarylalkanes and Triarylmethanes

  摘要：

  We have developed a stereospecific nickel-catalyzed cross-coupling of benzylic pivalates with arylboroxines. The success of this reaction relies on the use of Ni(cod)(2) as the catalyst and NaOMe as a uniquely effective base. This reaction has broad scope with respect to the arylboroxine and benzylic pivalate, enabling the synthesis of a variety of diarylalkanes and triarylmethanes in good to excellent yields and ee's.

  DOI：

  10.1021/ja312087x

文献信息

• The Substituent Effect. 14. The Solvolysis of 6- and 7-Substituted 1-(2-NaphthyI)ethyl Chlorides
  作者：Yuho Tsuno、Masami Sawada、Takahiro Fujii、Yasuhide Yukawa

  DOI：10.1246/bcsj.52.3033

  日期：1979.10

  and their solvolysis rates were determined in 80%(v/v) aq acetone at 45 °C. The effects of the pi-donor substituents for each substituent position are shown to be excellently described in terms of inductive(I) and pi-electronic(Pi) effects by means of the LSFE equation (logk⁄k0=ρiσi+ρπ+σπ+), Just as with those in the 1-naphthyl systems. When those data are joined with all our substituent effects data

  合成了 9 种标题化合物，并在 45 °C 下在 80%(v/v) 丙酮水溶液中测定了它们的溶剂分解率。通过 LSFE 方程 (logk⁄k0=ρiσi+ρπ+σπ+)，在电感 (I) 和 π 电子 (Pi) 效应方面，证明了对每个取代基位置的 pi 供体取代基的影响)，就像 1-萘基系统中的那些一样。当这些数据与我们在相同条件下苯基、4-联苯基、2-芴基和 1-萘基系统的所有取代基效应数据相结合时，很明显 ρi 值与杜瓦的简单场效应之间的总体对应关系功能 (1⁄r) 令人满意。另一方面，ρπ+ 值似乎对 SCF-π 电荷差异值给出了略微不同的响应（1- 和 2-萘基系统的单独相关性）；这可能归因于仅在 1-萘基溶剂分解组中对 Pi 效应的空间效应。此外，I 效应的位置恒定性 (ρi,6−X−2⁄ρi,7−X−2=...
• Rajasekaran, K.; Gnanasekaran, C., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1986, vol. 25, # 1, p. 64 - 66
  作者：Rajasekaran, K.、Gnanasekaran, C.

  DOI：——

  日期：——
• Nickel-Catalyzed Cross-Couplings of Benzylic Pivalates with Arylboroxines: Stereospecific Formation of Diarylalkanes and Triarylmethanes
  作者：Qi Zhou、Harathi D. Srinivas、Srimoyee Dasgupta、Mary P. Watson

  DOI：10.1021/ja312087x

  日期：2013.3.6

  We have developed a stereospecific nickel-catalyzed cross-coupling of benzylic pivalates with arylboroxines. The success of this reaction relies on the use of Ni(cod)(2) as the catalyst and NaOMe as a uniquely effective base. This reaction has broad scope with respect to the arylboroxine and benzylic pivalate, enabling the synthesis of a variety of diarylalkanes and triarylmethanes in good to excellent yields and ee's.