(2R)-(+)-phenylmethyl 2-vinylpyrrolidine-1-carboxylate | 623938-46-5

• 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: (2R)-(+)-phenylmethyl 2-vinylpyrrolidine-1-carboxylate
• 英文别名: (R)-2-vinylpyrrolidine-1-carboxylic acid benzyl ester；benzyl (R)-2-vinylpyrrolidine-1-carboxylate
• CAS: 623938-46-5
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: REODUIIKJBAGJE-ZDUSSCGKSA-N

物化性质

• 沸点：
  336.2±41.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  benzyl (E)-hex-4-en-1-yl((mesitylsulfonyl)oxy)carbamate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 (11aR)-(+)-10,11,12,13-tetrahydrodiindeno-[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以18%的产率得到(2R)-(+)-phenylmethyl 2-vinylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  N-（甲苯磺酰氧基）氨基甲酸酯的对映选择性 Aza-Heck 环化：吡咯烷和哌啶的合成

  摘要：

  用 SPINOL 衍生的氨基磷酸酯配体修饰的 Pd(0)-系统促进烯基 N-（甲苯磺酰氧基）氨基甲酸酯的高度对映选择性 aza-Heck 环化。该方法提供了对具有挑战性的 N-杂环的通用访问，并代表了迄今为止开发的最广泛的对映选择性 aza-Heck 协议。

  DOI：

  10.1021/jacs.8b12689

文献信息

• Gold(I)-Catalyzed Enantioselective Intramolecular Dehydrative Amination of Allylic Alcohols with Carbamates
  作者：Paramita Mukherjee、Ross A. Widenhoefer

  DOI：10.1002/anie.201107877

  日期：2012.2.6

  Aliphatic nitrogen heterocycles—either five‐ or six‐membered—are formed in high yield and with up to 94 % ee when a 1:2 mixture of [(S)‐2](AuCl)2 and AgClO4 is used as the catalyst for the title reaction.

  当 [( S )- 2 ](AuCl) 2和 AgClO 4的 1:2 混合物用作催化剂时，可以高产率地形成脂肪族氮杂环（五元或六元），ee高达 94% 为标题反应。
• Highly Chiral Muscarinic Ligands:  The Discovery of (2<i>S</i>,2‘<i>R</i>,3‘<i>S</i>,5‘<i>R</i>)-1-Methyl-2-(2-methyl-1,3-oxathiolan-5-yl)pyrrolidine 3-sulfoxide Methyl Iodide, a Potent, Functionally Selective, M₂ Partial Agonist
  作者：Serena Scapecchi、Rosanna Matucci、Cristina Bellucci、Michela Buccioni、Silvia Dei、Luca Guandalini、Cecilia Martelli、Dina Manetti、Elisabetta Martini、Gabriella Marucci、Marta Nesi、Maria Novella Romanelli、Elisabetta Teodori、Fulvio Gualtieri

  DOI：10.1021/jm0510878

  日期：2006.3.1

  the series [(-)-5, (-)-7, (+)-8] are endowed with functional activity and behave as M2 selective partial agonists. Among them, compound (2S,2'R,3'S,5'R)-1-methyl-2-(2-methyl-1,3-oxathiolan-5-yl)pyrrolidine 3-sulfoxide methyl iodide [(+)-8] is particularly interesting, as it is a potent partial agonist on guinea pig atrium (force) (M2; pD2=7.65, alpha=0.41) while being a poor antagonist on M1, M3, and

  通过先前研究的高度手性毒蕈碱激动剂的进一步空间复杂性，我们获得了对映异构和非对映异构的1-甲基-2-（2-甲基-1,3-氧硫杂环戊基-5-基）吡咯烷3-亚砜的小型手性文库。对在CHO细胞中表达的克隆的人类毒蕈碱受体的结合研究表明，引入第四个立体生成中心对hm1，hm3，hM4和hm5亚型具有不可检测的亲和力，而仅对hm2亚型具有相当适度的亲和力。但是，对模型M1-M4毒蕈碱组织的功能研究表明，[[-）-5，（-）-7，（+）-8]系列中的三种化合物具有功能活性并具有M2选择性部分激动剂的作用。 。其中，化合物（2S，2'R，3'S，5'R）-1-甲基-2-（2-甲基-1，