(S)-1-(2-(hydroxymethyl)pyrrolidin-1-yl)pent-4-en-1-one | 131080-60-9

• 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: (S)-1-(2-(hydroxymethyl)pyrrolidin-1-yl)pent-4-en-1-one
• 英文别名: N-(4-pentenoyl)-2-(hydroxymethyl)pyrrolidine；1-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pent-4-en-1-one
• CAS: 131080-60-9
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: MCQXOWJVXRHADN-VIFPVBQESA-N

物化性质

• 沸点：
  332.2±25.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-(hydroxymethyl)pyrrolidin-1-yl)pent-4-en-1-one 在 sodium hydride 、 四乙基对甲苯磺酸铵 作用下， 以 四氢呋喃 为溶剂， 反应 48.25h， 生成 5-methoxy-1-(pentenoyl)-2-<(benzyloxy)methyl>pyrrolidine
  参考文献：
  名称：

  Conformationally Restricted Peptide Mimetics: The Incorporation of 6,5-Bicyclic Lactam Ring Skeletons into Peptides

  摘要：

  This manuscript describes a convenient procedure for the synthesis of peptide fragments containing 6,5-bicyclic lactam-based conformational constraints. The syntheses capitalize on an electrochemical oxidation to functionalize a substituted proline derivative, an N-acyliminium ion-initiated cyclization in order to form a transient seven-membered-ring lactam, and a rearrangement reaction to form the desired six-membered-ring lactam. The bicyclic lactam products were converted into peptide building blocks and the stereochemistry of the building blocks assigned using two-dimensional NMR techniques. Once synthesized, the building blocks were readily incorporated into peptide fragments with the use of standard peptide synthesis techniques. The synthetic route employed was shown to be compatible with both aryl and branched amino acid side chains.

  DOI：

  10.1021/jo00130a015
• 作为产物：
  描述：

  4-戊烯酰氯 在 吡啶 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.83h， 生成 (S)-1-(2-(hydroxymethyl)pyrrolidin-1-yl)pent-4-en-1-one
  参考文献：
  名称：

  The Pent-4-enoyl Group: A Novel Amine-Protecting Group That Is Readily Cleaved under Mild Conditions

  摘要：

  Primary and secondary amines are readily protected as N-pent-4-enoyl derivatives, the resulting N-pent-4-enamides being usually highly crystalline. Deprotection is rapidly and efficiently effected under mild conditions by treatment with 3 equiv of iodine in aqueous THF solution. Although an oxidizing medium, these deprotection conditions do not affect oxidizable functionalities including p-methoxybenzyl ethers and alkyl sulfides.

  DOI：

  10.1021/jo00129a036

文献信息

• Anodic amide oxidations: Fundamental studies concerning the annulation of six- and seven-membered rings onto amines
  作者：Kevin D. Moeller、Scott L. Rothfus、Poh Lee Wong

  DOI：10.1016/s0040-4020(01)87048-4

  日期：1991.1

  electrochemically based annulation procedure for fusing six- and seven-membered rings onto amines has been examined. Both monosubstituted olefins and acetylenes were found to be good nucleophiles for annulating seven-membered rings onto amines. Disubstituted olefins and acetylenes appear to be good nucleophiles for completing the annulation of six-membered rings onto amines. In addition, the compatibility of

  已经研究了烯烃和炔属亲核试剂与用于将六元和七元环融合到胺上的基于电化学的环化程序的相容性。发现单取代的烯烃和乙炔都是将七元环环合到胺上的良好亲核试剂。二取代的烯烃和乙炔似乎是完成六元环在胺上环化的良好亲核试剂。此外，还研究了几种脯氨酸衍生物与环合程序的相容性。
• SONIC HEDGEHOG MODULATORS
  申请人：MASSACHUSETTS INSTITUTE OF TECHNOLOGY

  公开号：US20160046590A1

  公开（公告）日：2016-02-18

  Sonic Hedgehog modulators and methods of use thereof are provided for.

  提供了刺猬Sonic Hedgehog调节剂及其使用方法。
• Preparation of Nonracemic 3,5-Disubstituted-.gamma.-butyrolactones: An Effective Sequent Auxiliary for Amide Alkylation and Iodolactonization
  作者：Hongsik Moon、Shawn W. E. Eisenberg、Mark E. Wilson、Neil E. Schore、Mark J. Kurth

  DOI：10.1021/jo00101a002

  日期：1994.11

  The effective dual use of a chiral auxiliary in two sequential steps is reported; this sequent auxiliary mediates diastereoselective C-C bond formation in the first step and mediates diastereoselective heterocyclization in the second step.
• Enantioselective route to .gamma.-butyrolactones: chiral auxiliary mediated amide alkylation and iodolactonization
  作者：Samir Najdi、Daniel Reichlin、Mark J. Kurth

  DOI：10.1021/jo00313a005

  日期：1990.12

  A number of chiral, gamma, delta-unsaturated amides (1 and 2) have been prepared and their subsequent alkylation and iodolactonization to gamma-butyrolactones (3) investigated.
• NAJDI, SAMIR;REICHLIN, DANIEL;KURTH, MARK J., J. ORG. CHEM., 55,(1990) N6, C. 6241-6244
  作者：NAJDI, SAMIR、REICHLIN, DANIEL、KURTH, MARK J.

  DOI：——

  日期：——