allyl pyroglutamate | 4931-79-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: allyl pyroglutamate
• 英文别名: (±)-allyl 5-oxopyrrolidine-2-carboxylate；Prop-2-enyl 5-oxopyrrolidine-2-carboxylate
• CAS: 4931-79-7
• 化学式: C₈H₁₁NO₃
• mdl: MFCD24388809
• 分子量: 169.18
• InChiKey: ORDPRBNUVCKAST-UHFFFAOYSA-N

物化性质

• 沸点：
  342.8±35.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  allyl pyroglutamate 在 sodium tetrahydroborate 、 potassium phosphate 、 copper(l) iodide 、 sodium hydride 、 三(3,5-二甲基-1-吡唑基)甲烷 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 118.5h， 生成 (±)-methyl 2-((5-(allyloxymethyl)-1-phenylpyrrolidin-2-ylidene)amino)-5-methylbenzoate
  参考文献：
  名称：

  Synthesis of C-ring-modified blebbistatin derivatives and evaluation of their myosin II ATPase inhibitory potency

  摘要：

  (S)-Blebbistatin is a micromolar myosin II ATPase inhibitor that is extensively used in research. In search of analogs with improved potency, we have synthesized for the first time C-ring modified analogs. We introduced hydroxymethyl or allyloxymethyl functionalities in search of additional favorable interactions and a more optimal filling of the binding pocket. Unfortunately, the resulting compounds did not significantly inhibit the ATPase activity of rabbit skeletal-muscle myosin II. This and earlier reports suggest that rational design of potent myosin II inhibitors based on the architecture of the blebbistatin binding pocket is an ineffective strategy.

  DOI：

  10.1016/j.bmcl.2018.05.041
• 作为产物：
  描述：

  烯丙醇 、 DL-焦谷氨酸 在 calcium carbide 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以46%的产率得到allyl pyroglutamate
  参考文献：
  名称：

  吡咯烷酮的研究。具有杀菌和杀真菌性能的N-酰基焦谷氨酸酯的合成

  摘要：

  制备N-酰基焦谷氨酸酯的最佳方法是使N-三甲基甲硅烷基焦谷氨酸酯与酰氯或双烯酮反应。这些酰基酯具有针对几种微生物的杀菌和杀真菌特性。

  DOI：

  10.1002/jhet.5570250108

文献信息

• [EN] CONTROLLED RELEASE FROM MACROMOLECULAR CONJUGATES<br/>[FR] LIBÉRATION CONTRÔLÉE À PARTIR DE CONJUGUÉS MACROMOLÉCULAIRES
  申请人：PROLYNX LLC

  公开号：WO2011140393A1

  公开（公告）日：2011-11-10

  The invention relates to conjugates of macromolecular carriers and drugs comprising linkers that release the drug or a prodrug through rate-controlled beta-elimination, and methods of making and using the conjugates.

  这项发明涉及大分子载体和药物的共轭物，包括释放药物或前药的连接剂，通过速率控制的β-消除释放药物，以及制备和使用这些共轭物的方法。
• The Formation oftrans-Fused Macrocycles fromN3,N3′-Polymethylenebis(hydantoins) by Ring-Closing Metathesis
  作者：Diederica D. Claeys、Christian V. Stevens、Nicolai Dieltiens

  DOI：10.1002/ejoc.200700836

  日期：2008.1

  polymethylenebis(hydantoins) was extended, as these are HMBA analogues. Firstly, ethyl or allyl pyroglutamate was carbamoylated with a diisocyanate. Upon treatment with KOtBu in allyl alcohol the bis(carbamoyllactam) rearranged to give the hydantoin, which was followed by the ring-opening of the pyrrolidinone with formation of the allyl ester. These compounds were subsequently ring-closed in the presence

  得到聚亚甲基双（乙内酰脲）的直接环转化得到扩展，因为它们是 HMBA 类似物。首先，焦谷氨酸乙酯或焦谷氨酸烯丙酯用二异氰酸酯进行氨基甲酰化。在烯丙醇中用 KOtBu 处理后，双（氨基甲酰基内酰胺）重排得到乙内酰脲，随后吡咯烷酮开环形成烯丙酯。这些化合物随后在第二代格鲁布斯催化剂的存在下闭环，形成环中含有酯官能团的大环。通过反向检测的 HSQC 实验确定，在 24 和 26 元杂环的情况下，仅形成 E 异构体。
• CONTROLLED RELEASE FROM MACROMOLECULAR CONJUGATES
  申请人：Ashley Gary

  公开号：US20130116407A1

  公开（公告）日：2013-05-09

  The invention relates to conjugates of macromolecular carriers and drugs comprising linkers that release the drug or a prodrug through rate-controlled beta-elimination, and methods of making and using the conjugates.

  该发明涉及大分子载体和药物的共轭物，包括通过速率控制的β-消除释放药物或前药的连接剂，以及制备和使用这些共轭物的方法。
• Use of pyroglutamic acid alkyl esters for the manufacture of a medicament for the treatment of ichthyosis
  申请人：UNILEVER PLC

  公开号：EP0342055A2

  公开（公告）日：1989-11-15

  A therapeutic composition for the treatment of skin disorders comprises a therapeutically effective amount of a curative agent chosen from special esters of pyroglutamic acid, and mixtures thereof, in a therapeutically acceptable vehicle for topical application.

  一种用于治疗皮肤疾病的治疗组合物，包括一种治疗有效量的治疗剂，该治疗剂选自焦谷氨酸的特殊酯类及其混合物，并置于治疗上可接受的载体中，供局部使用。
• π-Facial Diastereoselection in [3 + 2]-Cycloadditions of Isomünchnone Dipoles
  作者：Albert Padwa、Michael Prein

  DOI：10.1021/jo970625o

  日期：1997.10.1

  The Rh(II)-catalyzed reaction of 1-[diazo(methoxycarbonyl)acetyl]-2-oxopyrrolidine derivatives led to the formation of ring-fused isomunchnone betaines which are trapped with various dipolarophiles to give the corresponding [3 + 2]-cycloadducts in excellent yield. The cycloaddition reaction proceeded with high levels of diastereoselectivity leading to the predominant formation of the exo dipolar cycloadduct. The influence of substituents on the stereoselectivity of the reaction was investigated. Diastereotopic facial selectivity by the dipolarophile on the mesoionic betaine was found to depend upon the nature of the stereogenic center. Inclusion of substituents at any position of the fused five-membered ring was found to enhance exo selectivity. Isomunchnone dipoles derived from pyrrolidinones containing a carboalkoxy substituent in the 5-position of the ring afforded mainly exo-syn cycloadducts. In contrast, when a methyl group was present at the 3-position of the pyrrolidinone ring, the facial selectivity was reversed with the exo-anti adduct being the major product. A computational study was carried out to rationalize the observed product distribution.