ethyl 3-(oxiran-2-yl)propanoate | 73697-60-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-(oxiran-2-yl)propanoate
• 英文别名: Ethyl 4,5-epoxy-4-pentenoate；Ethyl 4,5-epoxypentanoate；4,5-epoxy-valeric acid ethyl ester；4,5-Epoxy-valeriansaeure-aethylester；Ethyl (R,S)-4,5-epoxypentanoate；Oxiranepropanoic acid, ethyl ester
• CAS: 73697-60-6
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: MFZSRRBSNGQXRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(oxiran-2-yl)propanoate 在 氢气 作用下， 105.0 ℃ 、15.0 MPa 条件下， 反应 2.0h， 以99.7%的产率得到5-羟基戊酸乙酯
  参考文献：
  名称：

  一种用于制造δ-戊内酯的方法

  摘要：

  本发明提供了一种用于制造δ‑戊内酯的新方法。该方法包括：1)式(I)的乙酸烷基酯与环氧氯丙烷发生亲核取代反应，生成式(III)的4,5‑环氧基戊酸烷基酯；2)步骤1)所得式(III)的4,5‑环氧基戊酸烷基酯进行加氢反应生成式(IV)的5‑羟基戊酸烷基酯；3)步骤2)所得式(IV)的5‑羟基戊酸烷基酯发生环化反应生成δ‑戊内酯。本发明的方法反应总收率达95％以上。该方法原料廉价易得，对环境污染小，反应条件温和、成本低，产率高且产品易提纯，适合工业化生产。

  公开号：

  CN107987044B
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 3-(oxiran-2-yl)propanoate
  参考文献：
  名称：

  A practical one-pot radical-ionic sequence for the preparation of epoxides: application to the synthesis of unnatural polyhydroxylated alkaloids

  摘要：

  An efficient one-pot sequence for the preparation of epoxides from alpha-iodoesters or alpha-iodonitriles and allylic alcohols is described. This sequence is based on the use of iodine atom transfer reaction onto allylic alcohols followed by a ring closing epoxidation reaction of the halohydrin intermediates. The feasibility of this sequence is showcased in the synthesis of the perhydroaza-azulene, an unnatural analog of castanospermine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.042

文献信息

• Regio- and chemoselective rearrangement of terminal epoxides into methyl alkyl and aryl ketones
  作者：Yingying Tian、Eva Jürgens、Doris Kunz

  DOI：10.1039/c8cc06503a

  日期：——

  The development of the highly active pincer-type rhodium catalyst 2 for the nucleophilic Meinwald rearrangement of functionalised terminal epoxides into methyl ketones under mild conditions is presented. An excellent regio- and chemoselectivity is obtained for the first time for aryl oxiranes.

  提出了在温和条件下将官能化的末端环氧化物亲核性迈恩瓦尔德重排成甲基酮的高活性钳型铑催化剂2的开发。芳基环氧乙烷首次获得了优异的区域选择性和化学选择性。
• Piperazine, piperidine and tetrahydropyridine derivative of
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US05807857A1

  公开（公告）日：1998-09-15

  Compounds of formula (I), or a salt or prodrug thereof, wherein Z represents an optionally substituted five-membered heteroaromatic ring selected from furan, thiophene, pyrrole, oxazole, thiazole, isoxazole, isothiazole, imidazole, pyrazole, oxadiazole, thiadiazole, triazole and tetrazole; E represents a chemical bond or a straight or branched alkylene chain containing from 1 to 4 carbon atoms; Q represents a straight or branched alkylene chain containing from 1 to 6 carbon atoms, optionally substituted in any position by a hydroxy group; T represents nitrogen or CH; U represents nitrogen or C--R.sup.2 ; V represents oxygen, sulphur or N--R.sup.3 ; --F--G-- represents --CH2--N--, --CH2--CH-- or --CH.dbd.C--; R.sup.1 represents C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, aryl(C.sub.1-6)alkyl or heteroaryl(C.sub.1-6)alkyl, any of which groups may be optionally substituted; and R.sup.2 and R.sup.3 independently represent hydrogen or C.sub.1-6 alkyl are selective agonists of 5-HT1D receptors, being potent agonists of the human 5-HT1Dalpha receptor subtype, while possessing at least a 10-fold selective affinity for the 5-HT1Dalpha receptor subtype, relative to the 5-HT1Dbeta subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT1D receptors is indicated, while eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT1D receptor agonists.

  式(I)的化合物，或其盐或前药，其中Z代表从呋喃、噻吩、吡咯、噁唑、噻唑、异噁唑、异噻唑、咪唑、吡唑、噁二唑、噻二唑、三唑和四唑中选择的可选择性取代的五元杂芳环；E代表化学键或含有1至4个碳原子的直链或支链烷基链；Q代表含有1至6个碳原子的直链或支链烷基链，在任何位置可选择性地被羟基取代；T代表氮或CH；U代表氮或C--R.sup.2；V代表氧、硫或N--R.sup.3；--F--G--代表--CH2--N--，--CH2--CH--或--CH.dbd.C--；R.sup.1代表C.sub.3-6烯基、C.sub.3-6炔基、芳基(C.sub.1-6)烷基或杂芳基(C.sub.1-6)烷基，其中任何一个基团可选择性地被取代；而R.sup.2和R.sup.3独立地代表氢或C.sub.1-6烷基，是5-HT1D受体的选择性激动剂，是人类5-HT1Dα受体亚型的有效激动剂，同时相对于5-HT1Dbeta亚型，具有至少10倍的选择性亲和力；因此，在治疗和/或预防临床病症方面特别是偏头痛及相关疾病方面，对于需要5-HT1D受体亚型选择性激动剂的情况，比非亚型选择性5-HT1D受体激动剂引起的副作用更少，尤其是不良心血管事件。
• The conversion of racemic terminal epoxides into either (+)- or (−)-diol γ- and δ-lactones
  作者：Zhi-Yu Liu、Jian-Xin Ji、Bo-Gang Li

  DOI：10.1039/b003793l

  日期：——

  The conversion of racemic terminal epoxides into either (+)- or (−)-diol γ- and δ-lactones is described with hydrolytic kinetic resolution (HKR) as the key step.

  描述了将外消旋末端环氧化物转化为(+)-或(−)-diol γ-和δ-内酯的方法，其中水解动力学拆分（HKR）是关键步骤。
• Piperazine, piperidine and tetrahydropyridine derivatives
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US05977116A1

  公开（公告）日：1999-11-02

  A class of N-substituted piperazine, piperidine and tetrahydropyridine derivatives, linked by a fluoro-substituted alkylene chain to a fused bicyclic heteroaromatic moiety such as indolyl, and further substituted at the 4-position by an optionally substituted alkenyl, alkynyl, aryl-alkyl or heteroaryl-alkyl moiety, are selective agonists of 5-HT.sub.1 -like receptors, being potent agonists of the human 5-HT.sub.1D.alpha. receptor subtype whilst possessing at least a 10-fold selective affinity for the 5-HT.sub.1D.alpha. receptor subtype relative to the 5-HT.sub.1D.beta. subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT.sub.1D receptors is indicated, whilst eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT.sub.1D recptor agonists.

  一类N-取代哌嗪、哌啶和四氢吡啶衍生物，通过含氟取代的烷基链连接到融合的双环杂芳基团（如吲哚），并在4-位进一步取代为可选择取代的烯烃基、炔基、芳基-烷基或杂芳基-烷基团，是5-HT.sub.1-类受体的选择性激动剂，是人类5-HT.sub.1D.alpha.受体亚型的有效激动剂，同时相对于5-HT.sub.1D.beta.亚型具有至少10倍的选择性亲和力；因此，它们在治疗和/或预防临床疾病中特别是偏头痛及相关疾病方面具有用处，这些疾病需要5-HT.sub.1D受体的亚型选择性激动剂，同时引起的副作用较少，尤其是不良心血管事件，相比于与非亚型选择性5-HT.sub.1D受体激动剂相关的副作用。
• TiCl₄-Promoted Tandem Carbonyl or Imine Addition and Friedel–Crafts Cyclization: Synthesis of Benzo-Fused Oxabicyclooctanes and Nonanes
  作者：Arun K. Ghosh、Cuthbert D. Martyr、Chun-Xiao Xu

  DOI：10.1021/ol300494q

  日期：2012.4.20

  A new and convenient synthesis of benzo-fused 8-oxabicyclo[3.2.1]octane and 9-oxabicyclo[4.2.1]nonane derivatives are described. The reaction involved a TiCl4-mediated tandem carbonyl or imine addition followed by a Friedel–Crafts cyclization to provide these functionalized derivatives in good to excellent yields and high diastereoselectivity.

  描述了苯并稠合的 8-氧杂双环 [3.2.1] 辛烷和 9-氧杂双环 [4.2.1] 壬烷衍生物的新型便捷合成方法。该反应涉及 TiCl 4介导的串联羰基或亚胺加成，然后是 Friedel-Crafts 环化，以提供这些功能化的衍生物，收率非常好，并且具有高非对映选择性。