[2E]-2-Cyano-3-phenylprop-2-enol | 131202-39-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: [2E]-2-Cyano-3-phenylprop-2-enol
• 英文别名: [E]-α-Cyanocinnamyl alcohol；(E)-2-(hydroxymethyl)-3-phenylprop-2-enenitrile
• CAS: 131202-39-6
• 化学式: C₁₀H₉NO
• 分子量: 159.188
• InChiKey: YABIRQWDGVZHLL-UXBLZVDNSA-N

物化性质

• 沸点：
  350.3±30.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  [2E]-2-Cyano-3-phenylprop-2-enol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以71%的产率得到2-Cyano-3-phenylpropenal
  参考文献：
  名称：

  Applications of the Baylis-Hillman Adducts in Organic Synthesis: A Facile Synthesis of [E]-α-Cyanocinnamyl Alcohols and [E]-α-Cyanocinnamic Aldehydes

  摘要：

  介绍了在水硫酸介导下将 Baylis-Hillman 加合物（即 3-芳基-3-羟基-2-亚甲基丙腈）转化为 [E]-δ±-氰基肉桂醇，然后用 PCC 氧化，形成立体化学纯的 [E]-δ±-氰基肉桂醛，这是克诺文纳格尔缩合反应的一种有效替代途径。

  DOI：

  10.1055/s-1999-2893
• 作为产物：
  描述：

  2-丙烯腈,2-(溴甲基)-3-苯基-,(Z)- 在 盐酸 、 甲醇 作用下， 以 乙腈 为溶剂， 反应 15.0h， 生成 [2E]-2-Cyano-3-phenylprop-2-enol
  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

文献信息

• Hypervalent iodine catalysis for selective oxidation of Baylis–Hillman adducts via in situ generation of o-iodoxybenzoic acid (IBX) from 2-iodosobenzoic acid (IBA) in the presence of oxone
  作者：Raktani Bikshapathi、Parvathaneni Sai Prathima、Vaidya Jayathirtha Rao

  DOI：10.1039/c6nj02628a

  日期：——

  An efficient, environmentally benign, eco-friendly protocol for selective oxidation of primary and secondary Baylis–Hillman alcohols to the corresponding carbonyl compounds has been developed. We have demonstrated the catalytic use of o-iodoxybenzoic acid (IBX) generated in situ from 2-iodosobenzoic acid (IBA) in the presence of oxone (2KHSO5·KHSO4·K2SO4) as a co-oxidant. This efficient method notably

  已经开发出一种有效的，对环境无害的，环境友好的方案，用于将伯利兹和仲伯利兹-希尔曼醇选择性氧化为相应的羰基化合物。我们已经证明了在氧酮（2KHSO 5 ·KHSO 4 ·K 2 SO 4）作为助氧化剂存在下，由2-碘代苯甲酸（IBA）原位生成的邻碘氧苯甲酸（IBX）的催化用途。这种有效的方法尤其可以在不使用任何有毒重金属和直接使用棘手的IBX的情况下更好地提高产量。此外，可以通过还原后处理方便地回收合成的催化剂。
• Synthesis of stereochemically defined (E)-cinnamyl alcohol derivatives from the Baylis–Hillman adducts
  作者：Hyoung Shik Kim、Tae Yi Kim、Ka Young Lee、Yun Mi Chung、Hong Jung Lee、Jae Nyoung Kim

  DOI：10.1016/s0040-4039(00)00229-x

  日期：2000.4

  The reaction of the Baylis–Hillman adducts 1a–g and trifluoroacetic acid at 30–70°C gave the rearranged cinnamyl alcohols 2a–g stereoselectively in moderate yields.

  Baylis–Hillman加合物1a – g和三氟乙酸在30–70°C的反应以中等收率选择性地重排了肉桂醇2a – g。
• A Simple Route to 3-Substituted 2-Cyano Allylic Alcohols
  作者：Mouna Aiai、Michèle Baudy-Floc’h、Albert Robert、Philippe Le Grel

  DOI：10.1055/s-1996-4214

  日期：1996.3

  The first original and simple route to 3-substituted 2-cyano allylic alcohols with very good yields is described. The epoxide function in the key step acts as a protecting group during the synthesis of these allylic alcohols.

  描述了第一个以非常好的收率制备 3-取代 2-氰基烯丙醇的原始且简单的路线。关键步骤中的环氧化物官能团在这些烯丙醇的合成过程中充当保护基团。
• Electrochemical, Regioselective, and Stereoselective Synthesis of Allylic Thioethers and Selenoethers under Transition-Metal-Free and Oxidant-Free Conditions
  作者：Kusum Ucheniya、Amreen Chouhan、Lalit Yadav、Pooja Kumari Jat、Satpal Singh Badsara

  DOI：10.1021/acs.joc.3c00473

  日期：2023.5.5

  coupling protocol between allylic iodides and disulfides/diselenides for the formation of C–S/Se bonds in the absence of transition metals, bases, and oxidants. The stereochemically different densely functionalized allylic iodides gave regio- and stereoselective diverse thioethers in good yields. This strategy demonstrates a sustainable promising approach for the synthesis of allylic thioethers in 38–80%

  我们公开了一种温和的、可扩展的、电促进的烯丙基碘化物和二硫化物/二硒化物之间的交叉偶联方案，用于在没有过渡金属、碱和氧化剂的情况下形成 C-S/Se 键。立体化学不同的密集官能化烯丙基碘化物以良好的产率提供了区域选择性和立体选择性的不同硫醚。该策略展示了一种可持续的有前途的合成烯丙基硫醚的方法，产率为 38-80%。该协议还为烯丙基硒醚的合成提供了一个合成平台。还通过自由基清除剂实验和循环伏安法数据验证了单电子转移自由基途径。
• A simple protocol for the synthesis of a piperidine-2,6-dione framework from Baylis–Hillman adducts
  作者：Deevi Basavaiah、Dandamudi V. Lenin、Badugu Devendar

  DOI：10.1016/j.tetlet.2009.03.038

  日期：2009.7

  3-Hydroxy-2-methylenealkanenitriles, the Baylis-Hillman alcohols, derived from various aldehydes and acrylonitrile, have been conveniently transformed into 3-arylidene(or alkylidene)piperidine-2,6-diones in an operationally simple one-pot multi-step process involving Johnson-Claisen (J-C) rearrangement, partial hydrolysis, and cyclization. Rearranged Baylis-Hillman alcohols, (E)-2-hydroxymethyl-3-arylprop-2-enenitriles, have been converted into 4-aryl-3-methylidenepiperidine-2,6-diones in a similar reaction sequence. 4-Aryl-3,5-dimethylidenepiperidine-2,6-dione derivatives have been synthesized from Baylis-Hillman compounds, 3-aryl-4-cyano-2-methoxycarbonylpenta-1,4-dienes, obtained via the Baylis-Hillman reaction of methyl (2Z)-2-(bromomethyl)-3-arylprop-2-enoates with acrylonitrile, in a one-pot process. (C) 2009 Elsevier Ltd. All rights reserved.