1-propenyl-pyrrolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-propenyl-pyrrolidin-2-one
• 英文别名: 1-(prop-1-en-1-yl)pyrrolidin-2-one；N-propenyl-pyrrolidone；1-prop-1-enylpyrrolidin-2-one
• 化学式: C₇H₁₁NO
• 分子量: 125.17
• InChiKey: BFYSJBXFEVRVII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-propenyl-pyrrolidin-2-one 在 ruthenium trichloride 、 sodium periodate 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 2-氧吡咯烷-1-甲醛
  参考文献：
  名称：

  钌，酰胺，内酰胺，酰亚胺和同类物中烯丙基保护基的实际钌催化裂解。

  摘要：

  开发了一种方便的方法，用于脱保护N-烯丙基酰胺样部分。通过顺序使用Grubbs卡宾（异构化步骤）和RuCl（3）（氧化步骤）获得了第一个实例，说明了钌催化的酰胺，内酰胺，酰亚胺，吡唑烷酮，乙内酰脲和恶唑烷酮的脱羧反应。可以使用多种底物，包括对映纯多功能β-和γ-内酰胺。

  DOI：

  10.1002/chem.200501227
• 作为产物：
  描述：

  1-(烯丙基)吡咯烷-2-酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.5h， 生成 1-propenyl-pyrrolidin-2-one
  参考文献：
  名称：

  Radiosynthesis of ¹¹C-Levetiracetam: A Potential Marker for PET Imaging of SV2A Expression

  摘要：

  The multistep preparation of C-11-levetiracetam ((CLEV)-C-11) was carried out by a one-pot radiosynthesis with 8.3 +/- 1.6% (n = 8) radiochemical yield in 50 +/- 5.0 min. Briefly, the propionaldehyde was converted to propan-l-imine in situ as labeling precursor by incubation with ammonia. Without further separation, the imine was reacted with C-11-HCN to form C-11-aminonitrile. This crude was then reacted with 4-chlorobutyryl chloride and followed by hydrolysis to yield C-11-LEV after purification by chiral high-performance liquid chromatography (HPLC). Both the radiochemical and enantiomeric purities of C-11-LEV were >98%.

  DOI：

  10.1021/ml500285t

文献信息

• Iron(III)-Mediated Oxysulfonylation of Enamides with Sodium and Lithium Sulfinates
  作者：Philipp Kramer、Miro Halaczkiewicz、Yu Sun、Harald Kelm、Georg Manolikakes

  DOI：10.1021/acs.joc.9b03299

  日期：2020.3.6

  the oxysulfonylated products in moderate to excellent yields. Moreover, the direct incorporation of sulfur dioxide into the sulfonylated products via organolithium chemistry has been achieved. The formed N-O-acetals are competent acylimine precursors. Their utilization as building blocks for the synthesis of biologically relevant β-amidosulfones is described as well.

  描述了铁与亚氨基磺酸盐和醇的铁介导的邻位双官能化。该反应在温和的条件下进行，并以中等至极好的收率提供氧磺酰化产物。此外，已经实现了通过有机锂化学将二氧化硫直接掺入磺酰化产物中。所形成的NO-乙缩醛是合格的嘧啶前体。还描述了它们作为合成生物学上相关的β-氨基砜的基础材料的用途。
• A Giese reaction for electron-rich alkenes
  作者：Qi Huang、Sankar Rao Suravarapu、Philippe Renaud

  DOI：10.1039/d0sc06341j

  日期：——

  terminal and non-terminal alkenes such as enol esters, alkenyl sulfides, enol ethers, silyl enol ethers, enamides and enecarbamates has been developed. The reactions are carried out at room temperature under air initiation in the presence of triethylborane acting as a chain transfer reagent and 4-tert-butylcatechol (TBC) as a source of hydrogen atom. The efficacy of the reaction is best explained by very

  已经开发了一种用于富电子末端和非末端烯烃例如烯醇酯、烯基硫化物、烯醇醚、甲硅烷基烯醇醚、烯酰胺和烯氨基甲酸酯的加氢烷基化的通用方法。反应在室温下在空气引发下在作为链转移试剂的三乙基硼烷和作为氢原子源的4-叔丁基儿茶酚 (TBC) 存在下进行。该反应的功效最好通过非常有利的极性效应来解释，该效应支持链式过程并最大限度地减少不希望的极性反应。手性N- (alk-1-en-1-yl)oxazolidin-2-ones的立体选择性加氢烷基化反应具有良好的非对映控制。
• Percutaneous absorption-type pharmaceutical preparation
  申请人：Inosaka Keigo

  公开号：US20060275354A1

  公开（公告）日：2006-12-07

  A stable percutaneous absorption-type pharmaceutical preparation for percutaneous administration of drugs except for selegiline and selegiline hydrochloride, which does not suffer a decrease in the cohesive force of the adhesive layer therein even in the presence of sweat components due to perspiration during wear and which is free from cohesive failure and resultant adhesive remaining when stripped off. A percutaneous absorption-type pharmaceutical preparation which comprises: a support; and an adhesive layer containing an adhesive, a metal chloride and a percutaneously-absorptive drug except for selegiline and selegiline hydrochloride, wherein the adhesive layer is subjected to a crosslinking treatment.

  一种稳定的经皮吸收型药物制剂，用于除去赛洛吉林和赛洛吉林盐酸盐以外的药物的经皮给药，即使在穿戴过程中由于出汗而存在汗液成分时也不会减少粘合层的粘合力，并且在剥离时不会出现内聚力失效和残留粘合剂。一种经皮吸收型药物制剂，包括：一种支撑物；和一个含有粘合剂、金属氯化物和除赛洛吉林和赛洛吉林盐酸盐之外的经皮吸收药物的粘合层，其中粘合层经过交联处理。
• A Photochemical Two-Step Formal [5+2] Cycloaddition: A Condensation–Ring-Expansion Approach to Substituted Azepanes
  作者：Scott Thullen、David Rubush、Tomislav Rovis

  DOI：10.1055/s-0036-1589049

  日期：2017.12

  relatively understudied photochemical rearrangement of N-vinylpyrrolidinones to azepin-4-ones in good yields. This transformation allows for the conversion of readily available pyrrolidinones and aldehydes to densely functionalized azepane derivatives in a facile two step procedure.

  与其五元和六元类似物相比，七元含氮杂环在文献中的代表性明显不足。在此，我们报告了相对未充分研究的 N-乙烯基吡咯烷酮以良好产率将光化学重排为 azepin-4-one。这种转化允许在一个简单的两步程序中将容易获得的吡咯烷酮和醛转化为密集官能化的氮杂环庚烷衍生物。
• Re(I)-catalyzed hydropropargylation of enamides: a useful method for the preparation of 4-pentynylamine derivatives
  作者：Shoya Watanabe、Akane Ario、Nobuharu Iwasawa

  DOI：10.1038/s41429-019-0162-3

  日期：2019.6

  complex intermediate, followed by intramolecular hydrogen transfer to the iminium carbon. This method is useful for the synthesis of 4-pentynylamine derivatives from enamides and easily available propargyl ether. Moreover, tandem cyclization reaction was achieved to afford a pyrrolidine derivative in a single operation by using a secondary enamide.

  通过将酰胺的1，4-加成到α，β-不饱和卡宾配合物中间体上，然后将分子内的氢转移到亚胺碳上，可以以高收率实现酰胺的加氢炔丙基化。该方法可用于由酰胺和容易获得的炔丙基醚合成4-戊炔胺衍生物。此外，通过使用仲烯酰胺在一次操作中实现串联环化反应以提供吡咯烷衍生物。