3-Hydroxy-2-methylideneoctanenitrile | 22056-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Hydroxy-2-methylideneoctanenitrile
• CAS: 22056-02-6
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: AJBOTJSEBIQYDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  110-111 °C(Press: 2.4 Torr)
• 密度：
  0.938±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-2-methylideneoctanenitrile 在 三溴化磷 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 13.0h， 生成 2-cyanooct-2-enyl formate
  参考文献：
  名称：

  A New and Efficient Method for the Isomerization of Secondary Functional Allylic Alcohols into their Primary Isomers

  摘要：

  DOI：

  10.1055/s-1998-2220
• 作为产物：
  描述：

  正己醛 、 丙烯腈 在 三乙烯二胺 作用下， 以 neat (no solvent) 为溶剂， 生成 3-Hydroxy-2-methylideneoctanenitrile
  参考文献：
  名称：

  碘介导通过烯丙基腙中间体从 MBH 乙酸酯一锅法合成 1,4,5-取代吡唑

  摘要：

  描述了通过 Morita-Baylis-Hillman 乙酸酯和肼之间以烯丙基腙为中介的碘介导反应，一锅法区域选择性合成 1,4,5-吡唑。

  DOI：

  10.1002/ejoc.202300355

文献信息

• An efficient synthesis of Baylis–Hillman adducts of acrylamide: Pd-catalyzed hydration of Baylis–Hillman adducts of acrylonitrile
  作者：Eun Sun Kim、Hyun Seung Lee、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2009.08.127

  日期：2009.11

  An efficient palladium-catalyzed two-step protocol for the synthesis of Baylis–Hillman adducts of acrylamide was developed. The method involved the preparation of Baylis–Hillman adducts of acrylonitrile and a Pd-catalyzed hydration of nitrile with acetaldoxime.

  开发了一种有效的钯催化两步法合成丙烯酰胺的Baylis-Hillman加合物。该方法涉及丙烯腈Baylis-Hillman加合物的制备以及乙二醛与乙醛肟的Pd催化水合反应。
• The Friedel-Crafts reaction of the Baylis-Hillman adducts
  作者：Deevi Basavaiah、Marimganti Krishnamacharyulu、Rachakonda Suguna Hyma、Subramanian Pandiaraju

  DOI：10.1016/s0040-4039(97)00266-9

  日期：1997.3

  A simple and convenient methodology for the stereoselective construction of 2-benzyl substituted trisubstituted olefins via sulfuric acid catalyzed Fredel-Crafts reaction of benzene with Baylis-Hillman adducts is described.

  描述了一种简单方便的方法，用于通过硫酸催化苯与Baylis-Hillman加合物的立体催化构造2-苄基取代的三取代的烯烃。
• APPLICATION OF TMSOTf IN THE BAYLIS-HILLMAN ADDUCTS
  作者：Subramanian Ravichandran

  DOI：10.1081/scc-100104835

  日期：2001.1

  A simple and convenient methodology for the stereoselective construction of 2-benzyl substituted trisubstituted olefins1-2 via TMSOTf catalyzed reaction of benzene with Baylis- Hillman adducts is described.

  描述了通过 TMSOTf 催化苯与 Baylis-Hillman 加合物反应立体选择性构建 2-苄基取代的三取代烯烃 1-2 的简单方便的方法。
• Selenonium ionic liquid as efficient catalyst for the Baylis–Hillman reaction
  作者：Eder J. Lenardão、Josiane de Oliveira Feijó、Samuel Thurow、Gelson Perin、Raquel G. Jacob、Claudio C. Silveira

  DOI：10.1016/j.tetlet.2009.06.132

  日期：2009.9

  The new acidic ionic liquid phenyl butyl ethyl selenomum tetrafluoroborate, [pbeSe]BF4, Was Successful used as a co-catalyst in the Baylis-Hillman reaction of aldehydes and electron-deficient alkenes. The Baylis-Hillman adducts were obtained in moderated to good yields and in relatively short reaction times under mild conditions. (C) 2009 Elsevier Ltd. All rights reserved.
• Sulpholane––A new solvent for the Baylis–Hillman reaction
  作者：Palakodety Radha Krishna、A. Manjuvani、V. Kannan、G.V.M. Sharma

  DOI：10.1016/j.tetlet.2003.11.137

  日期：2004.2

  Sulpholane, a commercially available solvent, is used for the first time as a new solvent for the Baylis-Hillman reaction tinder ambient conditions; a wide variety of olefins as well as aldehydes participate very efficiently resulting in good to excellent yields of products. Acrylamide also underwent the Baylis-Hillman reaction with 4-nitrobenzaldehyde under these reaction conditions. (C) 2003 Elsevier Ltd. All rights reserved.