4-(hydroxyheptyl)-benzonitrile | 212197-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(hydroxyheptyl)-benzonitrile
• 英文别名: 4-(1-hydroxyheptyl)benzonitrile；4-(1-Hydroxyheptyl)benzonitrile
• CAS: 212197-71-2
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: NBHIJUZUTDLXGC-UHFFFAOYSA-N

物化性质

• 沸点：
  359.8±25.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-碘己烷 、 4-氰基苯甲醛 在 indium chloride copper(l) iodide 、 sodium oxalate 、 锌 作用下， 以14%的产率得到4-(hydroxyheptyl)-benzonitrile
  参考文献：
  名称：

  使用未活化的烷基卤在水中进行 Barbier-Grignard 型羰基烷基化

  摘要：

  开发了醛与未活化的烷基碘和溴化物的水性 Barbier-Grignard 型烷基化反应。通过使用由氯化铟 (I) 催化的锌和碘化亚铜的组合，我们成功地将叔、仲和伯烷基卤化物添加到 0.07 M Na2C2O4 水溶液中的各种芳香醛中。已经提出了反应成功的机械原理。

  DOI：

  10.1021/ja029649p

文献信息

• Chromium-Catalyzed Linear-Selective Alkylation of Aldehydes with Alkenes
  作者：Yuki Hirao、Yuri Katayama、Harunobu Mitsunuma、Motomu Kanai

  DOI：10.1021/acs.orglett.0c03180

  日期：2020.11.6

  We developed a chromium-catalyzed, photochemical, and linear-selective alkylation of aldehydes with alkylzirconium species generated in situ from a wide range of alkenes and Schwartz’s reagent. Photochemical homolysis of the C–Zr bond afforded alkyl radicals, which were then trapped by a chromium complex catalyst to generate the alkylchromium(III) species for polar addition to aldehydes. The reaction

  我们开发了铬催化，光化学和线性选择的醛醛烷基化反应，以及从各种烯烃和Schwartz试剂中就地生成的烷基锆物种。C-Zr键的光化学均质化提供了烷基，然后被铬络合物催化剂捕获，从而生成了烷基铬（III）物种，用于极性加成到醛中。反应在可见光照射下于环境温度下以高官能团耐受性进行。
• Halogen-Magnesium Exchange via Trialkylmagnesates for the Preparation of Aryl- and Alkenylmagnesium Reagents
  作者：Kazuya Kitagawa、Atsushi Inoue、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1002/1521-3773(20000717)39:14<2481::aid-anie2481>3.0.co;2-j

  日期：2000.7.17
• Selective Halogen−Magnesium Exchange Reaction via Organomagnesium Ate Complex
  作者：Atsushi Inoue、Kazuya Kitagawa、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1021/jo015597v

  日期：2001.6.1

  Halogen-magnesium exchange of various aryl halides is achieved with a magnesium ate complex at low temperatures; Tributylmagnesate ((Bu3MgLi)-Bu-n) induces facile iodine-magnesium exchange at -78 degreesC. Dibutylisopropylmagnesate ((PrBu2MgLi)-Pr-i-Bu-n) is more reactive than (Bu3MgLi)-Bu-n, and this reagent accomplishes selective bromine-magnesium exchange at -78 degreesC. This procedure is utilized for the preparation of various polyfunctionalized arylmagnesium species. The exchange of alkenyl halides using this method proceeds with retention of configuration of the double bond.
• Preparation of Highly Functionalized Grignard Reagents by an Iodine-Magnesium Exchange Reaction and its Application in Solid-Phase Synthesis
  作者：Laure Boymond、Mario Rottländer、Gérard Cahiez、Paul Knochel

  DOI：10.1002/(sici)1521-3773(19980703)37:12<1701::aid-anie1701>3.0.co;2-u

  日期：1998.7.3

  At -40°C aryl iodides that contain other functional groups can be selectively converted into Grignard reagents, which react with electrophiles such as benzaldehyde in the usual manner [Eq. (a)]. Aryl bromides and iodides that are immobilized as esters on a Wang resin behave analogously.
• The Barbier−Grignard-Type Carbonyl Alkylation Using Unactivated Alkyl Halides in Water
  作者：Charlene C. K. Keh、Chunmei Wei、Chao-Jun Li

  DOI：10.1021/ja029649p

  日期：2003.4.1

  The aqueous Barbier-Grignard-type alkylation of aldehydes with unactivated alkyl iodides and bromides was developed. By using a combination of zinc and cuprous iodide, catalyzed by indium(I) chloride, we successfully added tertiary, secondary, and primary alkyl halides to various aromatic aldehydes in 0.07 M aqueous Na2C2O4. A mechanistic rationale for the success of the reaction has been proposed

  开发了醛与未活化的烷基碘和溴化物的水性 Barbier-Grignard 型烷基化反应。通过使用由氯化铟 (I) 催化的锌和碘化亚铜的组合，我们成功地将叔、仲和伯烷基卤化物添加到 0.07 M Na2C2O4 水溶液中的各种芳香醛中。已经提出了反应成功的机械原理。