ethyl 9-cyanononanoate | 133309-93-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 9-cyanononanoate
• CAS: 133309-93-0
• 化学式: C₁₂H₂₁NO₂
• 分子量: 211.304
• InChiKey: PZAGFSBJUHCRJX-UHFFFAOYSA-N

物化性质

• 沸点：
  314.3±25.0 °C(Predicted)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 9-cyanononanoate 在 sodium phosphinate 、 水 、 sodium hexamethyldisilazane 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 顺-10-十八碳烯酸
  参考文献：
  名称：

  Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2

  摘要：

  It has been demonstrated previously that the endogenous compound N-arachidonyl-glycine inhibits the glycine transporter GlyT2, stimulates glycinergic neurotransmission, and provides analgesia in animal models of neuropathic and inflammatory pain. However, it is a relatively weak inhibitor with an IC50, of 9 mu M and is subject to oxidation via cyclooxygenase, limiting its therapeutic value. In this paper we describe the synthesis and testing of a novel series of monounsaturated C18 and C16 acyl-glycine molecules as inhibitors of the glycine transporter GIyT2. We demonstrate that they are up to 28 fold more potent that N-arachidonyl-glycine with no activity at the closely related GlyT1 transporter at concentrations up to 30 mu M. This novel class of compounds show considerable promise as a first generation of GIyT2 transport inhibitors.

  DOI：

  10.1021/acschemneuro.7b00105
• 作为产物：
  描述：

  9-溴壬酸 在 乙酰氯 作用下， 反应 22.0h， 生成 ethyl 9-cyanononanoate
  参考文献：
  名称：

  Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2

  摘要：

  It has been demonstrated previously that the endogenous compound N-arachidonyl-glycine inhibits the glycine transporter GlyT2, stimulates glycinergic neurotransmission, and provides analgesia in animal models of neuropathic and inflammatory pain. However, it is a relatively weak inhibitor with an IC50, of 9 mu M and is subject to oxidation via cyclooxygenase, limiting its therapeutic value. In this paper we describe the synthesis and testing of a novel series of monounsaturated C18 and C16 acyl-glycine molecules as inhibitors of the glycine transporter GIyT2. We demonstrate that they are up to 28 fold more potent that N-arachidonyl-glycine with no activity at the closely related GlyT1 transporter at concentrations up to 30 mu M. This novel class of compounds show considerable promise as a first generation of GIyT2 transport inhibitors.

  DOI：

  10.1021/acschemneuro.7b00105

文献信息

• Towards the rational design of palladium-N-heterocyclic carbene catalysts by a combined experimental and computational approach
  作者：Christopher J. O'Brien、Eric Assen B. Kantchev、Gregory A. Chass、Niloufar Hadei、Alan C. Hopkinson、Michael G. Organ、David H. Setiadi、Ting-Hua Tang、De-Cai Fang

  DOI：10.1016/j.tet.2005.07.101

  日期：2005.10

  approach towards the development of Pd–NHC catalysts is described. A range of benzimidazolylidinium ligands incorporating electron-rich and electron-poor substituents were prepared and evaluated in the Suzuki reaction. The most electron-rich ligand showed the highest catalytic activity. Based on this information, the first alkyl–alkyl Negishi cross-coupling reaction protocol was developed. Evaluation of

  描述了开发Pd-NHC催化剂的组合实验和计算方法。制备了一系列结合了富电子取代基和贫电子取代基的苯并咪唑基铱配体，并在Suzuki反应中进行了评估。最富电子的配体表现出最高的催化活性。基于此信息，开发了第一个烷基-烷基Negishi交叉偶联反应方案。对N，N′-二芳基-（4，5-二氢）咪唑基亚胺基鎓配体的评估显示出对金属中心周围的空间形貌的强烈依赖性。Negishi反应中活性最高的配体，其Pd（0）和PdCl 2的计算研究-复合物和相关结构是在B3LYP / DZVP和HF / 3-21G的理论水平上建模的。势能超表面随着配体尺寸的增加而变平。计算出卡宾/ Pd（0）加合物的结合能（约31–40 kcal mol -1），约为PH 3的结合能（约16 kcal mol -1）。使用AIM分析发现分子内相互作用较弱。
• Room-Temperature Negishi Cross-Coupling of Unactivated Alkyl Bromides with Alkyl Organozinc Reagents Utilizing a Pd/<i>N</i>-Heterocyclic Carbene Catalyst
  作者：Niloufar Hadei、Eric Assen B. Kantchev、Christopher J. O'Brien、Michael G. Organ

  DOI：10.1021/jo051304c

  日期：2005.10.1

  A high-yielding cross-coupling reaction of unactivated alkyl bromides possessing beta-hydrogens with alkylzinc halides utilizing a Pd/N-heterocyclic carbene (NHC) catalyst at room temperature is described. A variety of Pd sources, Pd-2(dba)(3), Pd(OAc)(2), or PdBr2, with the commercially available ligand precursor 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPr center dot HCl) successfully coupled 1-bromo-3-phenylpropane with n-butylzinc bromide in THF/NMP. An investigation of different NHC precursors showed that the bulky 2,6-diisopropylphenyl moiety was necessary to achieve high coupling yields (75-85%). The corresponding ethyl analogue was moderately active (11%). A range of unsymmetrical NHC precursors were prepared and evaluated. The ligand precursor containing one 2,6-diisopropylphenyl and one 2,6-diethylphenyl afforded the coupling product in 47% yield, clearly suggesting a direct relationship between the steric topography created by the flanking N-substituents and catalyst activity. Under optimal conditions, a number of alkyl bromides and alkylzinc halides possessing common functional groups (amide, nitrile, ester, acetal, and alkyne) were effectively coupled (61-92%). It is noteworthy that beta-substituted alkyl bromides and alkylzinc halides successfully underwent cross-coupling. Also, under these conditions alkyl chlorides were unaffected.
• The First Negishi Cross-Coupling Reaction of Two Alkyl Centers Utilizing a Pd−N-Heterocyclic Carbene (NHC) Catalyst
  作者：Niloufar Hadei、Eric Assen B. Kantchev、Christopher J. O'Brie、Michael G. Organ

  DOI：10.1021/ol0514909

  日期：2005.8.1

  The development of an NHC-based system capable of cross-coupling sp(3-)sp(3) centers in high yield has been a long-standing challenge. This communication describes the use of a Pd-NHC catalytic system that achieves room-temperature Negishi cross-couplings of unactivated, primary bromides and alkyl organozinc reagents with a variety of functionality.
• Alpha-(omega-cyanoalkanoyl)-gamma-butyrolactone and method for producing the same
  申请人：UBE INDUSTRIES, LTD.

  公开号：EP0402063B1

  公开（公告）日：1994-09-21
• US5023351A
  申请人：——

  公开号：US5023351A

  公开（公告）日：1991-06-11