6-羟基-1-环己烯-1-甲腈 | 28469-48-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-羟基-1-环己烯-1-甲腈
• 英文名称: 1-cyano 1-cyclohexene 6-ol
• 英文别名: 6-hydroxy-1-cyclohexene-1-carbonitrile；6-Hydroxy-1-cyclohexen-1-carbonitril；6-hydroxycyclohexene-1-carbonitrile
• CAS: 28469-48-9
• 化学式: C₇H₉NO
• 分子量: 123.155
• InChiKey: JGQMBKRQLBWMKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  6-羟基-1-环己烯-1-甲腈 在 吡啶 、 indium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4,4'-二甲基联苯
  参考文献：
  名称：

  Efficient Palladium-Catalyzed Nucleophilic Addition of Triorganoindium Reagents to Carbocyclic Derivatives

  摘要：

  Palladium (0)-catalyzed allylic substitution reactions employing triorganoindium reagents have been investigated. In situ generated vinyl- and arylindiums react with substituted and unsubstituted cyclohex-2-enyl esters in the presence of 1-3 mol % Pd-2(dba)(3) to produce vinyl- or arylcyclohexenes in moderate to excellent yields. The stereoselectivity of this process was also examined, and evidence is presented that the reaction proceeds with inversion of stereochemical configuration.

  DOI：

  10.1021/jo0357162
• 作为产物：
  描述：

  3-Hydroxy-2-methylideneoct-7-enenitrile 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到6-羟基-1-环己烯-1-甲腈
  参考文献：
  名称：

  Intramolecular Morita–Baylis–Hillman adducts via sequential MBH and ring-closing-metathesis reactions

  摘要：

  Using a tandem Morita-Baylis-Hiliman (MBH) and ring-closing-metathesis (RCM) sequence, an alternative high yielding method for the construction of intramolecular Morita-Baylis-Hillman (IMBH) mono- and bicyclic functionalized cycloalkenols is reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.066

文献信息

• Development of Aliphatic Alcohols as Nucleophiles for Palladium-Catalyzed DYKAT Reactions:  Total Synthesis of (+)-Hippospongic Acid A
  作者：Barry M. Trost、Michelle R. Machacek、Hong C. Tsui

  DOI：10.1021/ja050340q

  日期：2005.5.1

  The ability to use aliphatic alcohols as competent nucleophiles in the palladium-catalyzed dynamic kinetic asymmetric transformation of Baylis-Hillman adducts is explored. High yield and enantioselectivity is obtained for both the kinetic transformation and dynamic kinetic transformation. The absolute stereochemistry of the products is used to explore the reactive conformation of 2-substituted pi-allyl

  探索了在钯催化的 Baylis-Hillman 加合物的动态动力学不对称转化中使用脂肪醇作为感受态亲核试剂的能力。动力学转化和动态动力学转化均获得高产率和对映选择性。产品的绝对立体化学用于探索 2-取代的 pi-烯丙基配合物与基于 DPPBA 的手性配体的反应构象。在原肠形成抑制剂 (+)-河马酸 A 的简明全合成的背景下进一步证明了该方法的实用性。该合成具有三个钯催化的烯丙基烷基化反应，以引入三种不同的键类型：CS、CH 和公司。
• [EN] CYCLOALKYLNITRILE PYRAZOLE CARBOXAMIDES AS JANUS KINASE INHIBITORS<br/>[FR] CYCLOALKYLNITRILE PYRAZOLE CARBOXAMIDES EN TANT QU'INHIBITEURS DE JANUS KINASE
  申请人：MERCK SHARP & DOHME

  公开号：WO2013040863A1

  公开（公告）日：2013-03-28

  Cycloalkylnitrile pyrazole carboxamides as JAK inhibitors useful for the treatment of JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer are provided.

  提供环烷基腈吡唑羧酰胺作为JAK抑制剂，用于治疗JAK介导的疾病，如类风湿关节炎、哮喘、慢性阻塞性肺病和癌症。
• Copper-Catalyzed Asymmetric Allylic Alkylation of Racemic Cyclic Substrates: Application of Dynamic Kinetic Asymmetric Transformation (DYKAT)
  作者：Jean-Baptiste Langlois、Alexandre Alexakis

  DOI：10.1002/adsc.200900790

  日期：2010.2.15

  The copper-catalyzed asymmetric allylic alkylation (AAA) is of great interest in organic synthesis. This reaction was extensively studied using a broad range of substrates, ligands and organometallic reagents. However, the use of racemic substrates was still limited. Although some processes of kinetic resolution are reported in the literature, no examples of quantitative deracemization are described

  铜催化的不对称烯丙基烷基化（AAA）在有机合成中非常重要。使用各种各样的底物，配体和有机金属试剂对这一反应进行了广泛的研究。但是，外消旋底物的使用仍然受到限制。尽管在文献中报道了一些动力学拆分方法，但是没有描述定量脱氨的实例，如Pd催化的烯丙基烷基化的情况。在此，我们将通过在铜催化的AAA中开发这种方法的第一个实例来全面介绍我们的研究。本文报道了高对映选择性（高达99％ee），反应范围和机理考虑。
• La reaction de Wittig-Horner en milieu heterogene IX. Bis aldolisation des phosphonates a partir des dialdehydes aliphatiques en milieu aqueux peu basique. Synthese de cyclenols fonctionnels.
  作者：M. Graff、A. Al Dilaimi、P. Seguineau、M. Rambaud、J. Villieras

  DOI：10.1016/s0040-4039(00)84318-x

  日期：1986.1

  Aqueous solutions of glutaraldehyde and succinaldehyde give respectively improved yields of 1-functional 6-cyclohexenols and 5-cyclopentenols, when subjected to WITTIG-HORNER reaction in water at room temperature, with potassium carbonate as a base.

  当在室温下以碳酸钾为碱在水中进行WITTIG-HORNER反应时，戊二醛和丁二醛的水溶液分别提高了1-官能的6-环己醇和5-环戊烯醇的产率。
• ACYCLIC CYANOETHYLPYRAZOLES AS JANUS KINASE INHIBITORS
  申请人：Brubaker Jason

  公开号：US20140228358A1

  公开（公告）日：2014-08-14

  The instant invention provides compounds of formula I which are JAK inhibitors, and as such are useful for the treatment of JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer.

  本发明提供了I型化合物，它们是JAK抑制剂，因此可用于治疗JAK介导的疾病，如类风湿性关节炎、哮喘、慢性阻塞性肺疾病和癌症。