benzyl benzyl(2-oxoethyl)carbamate | 166947-03-1

• 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: benzyl benzyl(2-oxoethyl)carbamate
• 英文别名: benzyl N-benzyl-N-(2-oxoethyl)carbamate
• CAS: 166947-03-1
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: UHOFHKFKWIHWQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  432.1±44.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl benzyl(2-oxoethyl)carbamate 在 DL-脯氨酸 作用下， 以 乙腈 为溶剂， 反应 68.0h， 生成 ethyl hydrogen 2-{2-[(benzyl)(benzyloxycarbonyl)amino]-1-(1H-indol-3-yl)ethyl}malonate
  参考文献：
  名称：

  A Convenient Synthesis of Indole-Substituted 2-Pyrrolidones and Their Cyclized Derivatives

  摘要：

  Condensation between indole, Meldrum's acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a-c. The latter were cyclized to indole-substituted 2-pyrrolidones 15a-b or 3-aminopyrrolid-2-ones 18a-b, depending on the starting material. Derivative 18a was transformed into pyrrolo[3',4' :5,6]pyrido[3,4-b]indol-3(2H)-ones 19a and 20a by a Pictet-Spengler condensation with benzaldehyde.

  DOI：

  10.1002/1099-0690(200009)2000:17<3051::aid-ejoc3051>3.0.co;2-3
• 作为产物：
  描述：

  2,2-dimethoxy-N-(phenylmethylene)-1-ethanamine 在 盐酸 、 sodium tetrahydroborate 、 水 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 水 、 乙腈 为溶剂， 反应 38.0h， 生成 benzyl benzyl(2-oxoethyl)carbamate
  参考文献：
  名称：

  A Convenient Synthesis of Indole-Substituted 2-Pyrrolidones and Their Cyclized Derivatives

  摘要：

  Condensation between indole, Meldrum's acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a-c. The latter were cyclized to indole-substituted 2-pyrrolidones 15a-b or 3-aminopyrrolid-2-ones 18a-b, depending on the starting material. Derivative 18a was transformed into pyrrolo[3',4' :5,6]pyrido[3,4-b]indol-3(2H)-ones 19a and 20a by a Pictet-Spengler condensation with benzaldehyde.

  DOI：

  10.1002/1099-0690(200009)2000:17<3051::aid-ejoc3051>3.0.co;2-3

文献信息

• α‐Amidoaldehydes as Substrates in Rhodium‐Catalyzed Intermolecular Alkyne Hydroacylation: The Synthesis of α‐Amidoketones
  作者：Ritashree Pal、Sean C. O'Brien、Michael C. Willis

  DOI：10.1002/chem.202002478

  日期：2020.9.10

  substrates for intermolecular Rh‐catalyzed alkyne hydroacylation reactions. The catalyst [Rh(dppe)(C6H5F)][BArF4] provides good reactivity, and allows a broad range of aldehydes and alkynes to be used as substrates, delivering α‐amidoketone products. High yields and high levels of regioselectivity are achieved. The use of α‐amidoaldehydes as substrates establishes that 1,4‐dicarbonyl motifs can be used as controlling

  我们表明，现成的α-酰胺醛是分子间Rh催化炔烃加氢酰化反应的有效底物。催化剂[Rh（dppe）（C 6 H 5 F）] [BAr F 4 ]具有良好的反应活性，可将各种醛和炔烃用作底物，从而提供α-酰胺酮产品。实现了高产率和高水平的区域选择性。使用α-酰胺醛作为底物可确定1,4-二羰基可以用作Rh催化加氢酰化反应中的控制基团。
• α‐Hydroxy‐Tetrazoles as Latent Ethynyl Moieties: A Mechanistic Investigation
  作者：Pierre Quinodoz、Karen Wright、Bruno Drouillat、Mikhail E. Kletskii、Oleg N. Burov、Anton. V. Lisovin、François Couty

  DOI：10.1002/ejoc.201800143

  日期：2019.1.23

  This article focuses on the dehydration of α‐hydroxy‐tetrazoles, leading to tetraazafulvenes and then to vinylic carbenes that rearrange into ethynyl moieties through the Fritsch–Buttenberg–Wiechell rearrangement. Each step of this sequence was scrutinized, either by examination of the substrate and/or dehydrating agent scope, or through AM1 calculations, in order to understand the limiting step of

  本文着重于α-羟基四唑的脱水，导致四氮杂富烯，然后再通过Fritsch–Buttenberg–Wiechell重排而重排成乙炔基的乙烯基卡宾。通过检查底物和/或脱水剂的范围，或通过AM1计算，仔细检查该序列的每个步骤，以了解该方法的限制步骤。这种低估的转化似乎是用于将醛转化为炔烃的现有方法的可行替代方案。
• Total synthesis of (+)-swainsonine and (+)-8-epi-swainsonine
  作者：Milos Trajkovic、Vesna Balanac、Zorana Ferjancic、Radomir N. Saicic

  DOI：10.1039/c4ra11978a

  日期：——

  Enantioselective total synthesis of (+)-swaisonine that hinges on a combination of organocatalyzed aldolization and reductive amination, affords the title compound in 9 steps, with 24% overall yield.

  通过有机催化的Aldol缩合和还原胺化反应，对(+) -swaisonine进行对映选择性全合成，经过9个步骤，总产率为24%。
• [EN] HETEROCYCLIC DERIVATIVES AND THEIR USE AS ANTITHROMBOTIC AGENTS<br/>[FR] DERIVES HETEROCYCLIQUES ET LEUR UTILISATION EN TANT QU'AGENTS ANTITHROMBOTIQUES
  申请人：AKZO NOBEL N.V.

  公开号：WO1998047876A1

  公开（公告）日：1998-10-29

  (EN) The present invention relates to antithrombotic compounds comprising the group Q, Q having formula (I), wherein the substructure (i) is a structure selected from (a, b and c), wherein X is O or S; X' being independently CH or N; and m is 0, 1, 2 or 3; wherein the group Q is bound through an oxygen atom or an optionally substituted nitrogen or carbon atom, or a pharmaceutically acceptable salt thereof or a prodrug thereof. The compounds of the invention are therapeutically active and in particular are antithrombotic agents.(FR) La présente invention concerne des composé antithrombotiques comprenant le groupe Q correspondant à la formule (I) dans laquelle la sous-structure (i) est une structure choisie parmi (a), (b) ou (c) où X représente O ou S, X' représente indépendamment CH ou N, et m vaut 0, 1, 2 ou 3, le groupe Q étant fixé au moyen d'un atome d'oxygène ou d'un atome de carbone ou d'azote éventuellement substitué. L'invention concerne également un sel ou un promédicament de ces composés, acceptable sur le plan pharmacologique. Les compositions de l'invention sont actives sur le plan thérapeutique et constituent notamment des agents antithrombotiques.

  该发明涉及抗血栓化合物，包括具有公式（I）的Q基团，其中亚结构（i）是从（a）、（b）和（c）中选择的结构，其中X为O或S；X'独立地为CH或N；m为0、1、2或3；其中Q基团通过氧原子或可选择的取代氮或碳原子结合，或其药学可接受的盐或前药。该发明的化合物具有治疗活性，特别是抗血栓剂。
• Preparation of Substituted Piperazinones via Tandem Reductive Amination−(<i>N</i>,<i>N</i>‘-Acyl Transfer)−Cyclization
  作者：Douglas C. Beshore、Christopher J. Dinsmore

  DOI：10.1021/ol025644l

  日期：2002.4.1

  [GRAPHICS]A one-pot, tandem reductive amination-transamidation-cyclization reaction was employed to produce substituted piperazin-2-ones in good yields. Various amino acid methyl esters and transferable acyl groups were examined to establish the reaction's scope.