1-Pyrrolidinecarboxylic acid, 2-oxiranyl-, phenylmethyl ester, (2R)- | 623938-56-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Pyrrolidinecarboxylic acid, 2-oxiranyl-, phenylmethyl ester, (2R)-
• 英文别名: (2R)-phenylmethyl 2-(oxiran-2-yl)pyrrolidine-1-carboxylate
• CAS: 623938-56-7
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: VQVQKTLIXHDXCW-PZORYLMUSA-N

物化性质

• 沸点：
  378.8±35.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-Pyrrolidinecarboxylic acid, 2-oxiranyl-, phenylmethyl ester, (2R)- 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 异丙醇 为溶剂， 反应 98.25h， 生成 (S)-2-Amino-1-((R)-1-methyl-pyrrolidin-2-yl)-ethanol
  参考文献：
  名称：

  单手性5-（2-吡咯烷基）恶唑烷酮和2-（2-吡咯烷基）苯并二恶烷的合成及其α4β2烟碱亲和力。

  摘要：

  合成了分别在5-和2-位带有2-吡咯烷基取代基的2-恶唑烷酮和1,4-苯并二恶烷的RS和SR对映体，作为候选烟碱类化合物。两种苯并二恶烷立体异构体之一合理地适合（S）-尼古丁的药效团元素，并以亚微摩尔亲和力结合在α4beta2烟碱型乙酰胆碱受体上。有趣的是，两个合成的吡咯烷基苯并二恶烷在α（2）肾上腺素能受体上都表现出相似的亲和力，类似于一些最近被证明具有神经元烟碱亲和力的已知α（2）-AR配体的行为。

  DOI：

  10.1016/j.bmcl.2006.08.020
• 作为产物：
  描述：

  (2R)-(+)-phenylmethyl 2-vinylpyrrolidine-1-carboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以86.5%的产率得到1-Pyrrolidinecarboxylic acid, 2-oxiranyl-, phenylmethyl ester, (2R)-
  参考文献：
  名称：

  Synthesis and cholinergic affinity of diastereomeric and enantiomeric isomers of 1-methyl-2-(2-methyl-1,3-dioxolan-4-yl)- pyrrolidine, 1-methyl-2-(2-methyl-1,3-oxathiolan-5-yl)pyrrolidine and of Their iodomethylates

  摘要：

  Four out of the eight possible stereoisomers of 1-methyl-2-(2-methyl-1,3-dioxolan-4-yl)pyrrolidine, 1-methyl-2-(2methyl-1.3-oxathiolan-5-,I)pyrrolidine and the corresponding iodomethylates have been synthesised. They were formally derived from hybridisation of potent though unselective agonists studied before, such as 1,3-dioxolane 1 and 1,3-oxathiolane 2, with the structure of nicotine. It was expected that, by exalting the molecular complexity of the parent compounds, in particular through stereochemical complication in the proximity of the critical cationic head of the molecule, the chance to find agonists able to discriminate among cholinergic receptors subtypes would increase. The relative and absolute configuration of the compounds obtained has been established by means of NMR spectroscopy and X-ray crystallography. In preliminary studies, their binding affinity has been evaluated on rat brain nicotinic and muscarinic receptors. While none of the compounds showed any nicotinic affinity up to the dose of 10 muM, most of the iodomethylates were endowed with promising affinity for the muscarinic receptors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00236-0

文献信息

• Discovery of novel 1-arylmethyl pyrrolidin-2-yl ethanol amines as calcium-sensing receptor antagonists
  作者：Ashvinikumar V. Gavai、Roy J. Vaz、Amarendra B. Mikkilineni、Jacques Y. Roberge、Yalei Liu、R. Michael Lawrence、James R. Corte、Wu Yang、Mark Bednarz、John K. Dickson、Zhengping Ma、Ramakrishna Seethala、Jean H.M. Feyen

  DOI：10.1016/j.bmcl.2005.08.095

  日期：2005.12

  A 3D quantitative structure-activity relationship study for inhibition of calcium-sensing receptor in the aryloxypropanolamine series predicted that these molecules adopt a U-shaped conformation with pi-stacking between the two aromatic rings. This hypothesis led to the discovery of novel l-arylmethyl pyrrolidin-2-yl ethanol amines capable of antagonizing the calcium-sensing receptor with potency comparable to that of NPS-2143. (c) 2005 Elsevier Ltd. All rights reserved.