11-cyano-undecanoic acid ethyl ester | 52162-19-3

• 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: 11-cyano-undecanoic acid ethyl ester
• 英文别名: 11-Cyan-undecansaeure-aethylester；ω-Cyano-undecansaeure-ethylester；Ethyl 11-cyanoundecanoate
• CAS: 52162-19-3
• 化学式: C₁₄H₂₅NO₂
• 分子量: 239.358
• InChiKey: FUNUKWGHJKIQIE-UHFFFAOYSA-N

物化性质

• 沸点：
  196-198 °C(Press: 11 Torr)
• 密度：
  0.933±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  11-cyano-undecanoic acid ethyl ester 在 sodium phosphinate 、 水 、 sodium hexamethyldisilazane 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 2-[[(Z)-octadec-12-enoyl]amino]acetic acid
  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：

  1,1-二乙氧基环十二烷 在 盐酸 、 亚硝酸乙酯 、 乙醇 、 二氧化硫 作用下， 生成 11-cyano-undecanoic acid ethyl ester
  参考文献：
  名称：

  Nitrosation in organic chemistry. Nitrosolysis, a novel carbon-carbon bond cleavage effected through nitrosation. Nitrosolysis of ketones and ketone acetals

  摘要：

  DOI：

  10.1021/ja00446a031

文献信息

• Alpha-(omega-cyanoalkanoyl)-gamma-butyrolactone and method for producing the same
  申请人：UBE INDUSTRIES, LTD.

  公开号：EP0402063A2

  公开（公告）日：1990-12-12

  Disclosed are α-(ω-Cyanoalkanoyl)-γ-butyrolactone represented by the formula: wherein n represents an integer of 7 to 11, and a method for producing the same, which comprises reacting ω-cyano fatty acid ester represented by the formula: NC-(CH₂)n-COOR      (II) wherein R represents an alkyl group having 1 to 4 carbon atoms and n has the same meaning as in the above, with γ-butyrolactone in the presence of alkali metal alcoholate represented by the formula: R′OM      (III) wherein R′ represents an alkyl group having 1 to 4 carbon atoms and M represents an alkali metal.

  所公开的α-(ω-氰基烷酰基)-γ-丁内酯由式表示： 其中 n 代表 7 至 11 的整数、 以及一种生产该物质的方法，其中包括使由式.NC-(CH₂)代表的ω-氰基脂肪酸酯反应： NC-(CH₂)n-COOR (II) 其中 R 代表具有 1 至 4 个碳原子的烷基，n 的含义与上文相同、 与γ-丁内酯在碱金属醇酸酯存在下进行反应，碱金属醇酸酯的代表式为 R′OM (III) 其中 R′代表具有 1 至 4 个碳原子的烷基，M 代表碱金属。
• Barlow et al., British Journal of Pharmacology and Chemotherapy, 1955, vol. 10, p. 116,117
  作者：Barlow et al.

  DOI：——

  日期：——
• Neuberger, Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences, 1937, vol. 158, p. 93
  作者：Neuberger

  DOI：——

  日期：——
• 961. Synthesis of potential antibacterial agents. Part II. A pyrimidine analogue of chaulmoogric acid
  作者：T. D. Heyes、John C. Roberts

  DOI：10.1039/jr9520004935

  日期：——
• US5023351A
  申请人：——

  公开号：US5023351A

  公开（公告）日：1991-06-11