N-苄基-4-氧代-4-苯基丁酰胺 | 7510-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N-苄基-4-氧代-4-苯基丁酰胺
• 英文名称: N-benzyl-4-oxo-4-phenylbutanamide
• CAS: 7510-08-9
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: RRGZDQMVNQZKET-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C(Solv: ethanol (64-17-5))
• 沸点：
  509.4±43.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)
• 溶解度：
  >40.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-苄基-4-氧代-4-苯基丁酰胺 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 11.0h， 以93%的产率得到4-oxo-4-phenylbutanamide
  参考文献：
  名称：

  Selective N-debenzylation of amides with p-TsOH

  摘要：

  N-Benzylamides were debenzylated efficiently with 4 equiv. of p-TsOH in refluxing toluene. Good to quantitative yields of the desired primary amides were obtained within 2-4 h from a wide variety of N-2,4-dimethoxybenzylamides. N-4-Methoxyl-benzyl amides and N-benzylamides were also debenzylated cleanly. In the case of N-2,4-dimethoxylbenzylamides, selective N-debenzylation was possible in the presence of N-Fmoc, N-t-BOC or N-trityl-protection. Protected amino acid amides survived these conditions without any detectable epimerization. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02738-7
• 作为产物：
  描述：

  N-benzyl-4-hydroxy-4-phenyl-2-butynamide 在 Lindlar's catalyst 氢气 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 3.0h， 生成 N-苄基-4-氧代-4-苯基丁酰胺
  参考文献：
  名称：

  Coppola, Gary M.; Damon, Robert E., Journal of Heterocyclic Chemistry, 1995, vol. 32, # 4, p. 1133 - 1140

  摘要：

  DOI：

文献信息

• 3,3′-(Phenylphosphinylidene)bis[2(3<i>H</i>)-benzoxazolone] and 3,3′-(Phenylphosphinylidene)bis[2(3<i>H</i>)-benzothiazolone]. New Activating Agents
  作者：Mitsuru Ueda、Amane Mochizuki、Ichir\={o} Hiratsuka、Hideaki Oikawa

  DOI：10.1246/bcsj.58.3291

  日期：1985.11

  New activating agents, 3,3′-(phenylphosphinylidene)bis[2(3H)-benzoxazolone] (4) and 3,3′-(phenylphosphinylidene)bis[2(3H)-benzothiazolone] (5), were readily prepared by the reaction of phenylphosphonic dichloride (3) with 2(3H)-benzoxazolone (1) and 2(3H)-benzothiazolone (2) respectively in the presence of triethylamine at room temperature. The new activating agents 4 and 5 were found to be useful

  新的活化剂 3,3'-(苯基亚膦基)双 [2(3H)-苯并恶唑酮] (4) 和 3,3'-(苯基亚膦基)双[2(3H)-苯并噻唑酮] (5) 可以通过以下方式轻松制备在室温下，在三乙胺存在下，苯基膦酰二氯 (3) 分别与 2(3H)-苯并恶唑酮 (1) 和 2(3H)-苯并噻唑酮 (2) 反应。发现新的活化剂 4 和 5 可用于在温和条件下制备酰胺、酯和二肽。此外，间苯二甲酸与芳族二胺在吡啶存在下使用活化剂 4 的直接缩聚反应在室温下快速进行，以产生特性粘度高达 0.80 dL/g 的聚酰胺。
• Cobalt-Catalyzed Regioselective Synthesis of Pyrrolidinone Derivatives by Reductive Coupling of Nitriles and Acrylamides
  作者：Ying-Chieh Wong、Kanniyappan Parthasarathy、Chien-Hong Cheng

  DOI：10.1021/ja9088296

  日期：2009.12.30

  A convenient and highly regioselective method for the synthesis of 5-methylenepyrrolidinone derivatives from various nitriles and acrylamides via a cobalt-catalyzed reductive coupling reaction is described. A possible mechanism that involves the formation of a cobaltaazacyclopentene intermediate from nitrile and acrylamide, protonation, keto-amide cyclization, and dehydration is proposed.

  描述了一种方便且高度区域选择性的方法，用于通过钴催化还原偶联反应从各种腈和丙烯酰胺合成 5-亚甲基吡咯烷酮衍生物。提出了一种可能的机制，涉及从腈和丙烯酰胺形成钴氮杂环戊烯中间体、质子化、酮酰胺环化和脱水。
• Acid promoted cyclodehydration of amino alcohols with amide acetal
  作者：Soonho Hwang、Heemin Park、Yongseok Kwon、Sanghee Kim

  DOI：10.1039/c4ra10625c

  日期：——

  A convenient acid-promoted cyclization protocol for the formation of azaheterocycles from amino alcohols is described. The reaction involves the use of N,N-dimethylacetamide dimethyl acetal (DMADA) as the activating reagent of the hydroxyl group. Using this protocol, pyrrolidines or piperidines with various substituents can be synthesized in good to high yields.

  描述了一种方便的酸促进的环化方案，用于从氨基醇形成氮杂杂环。该反应涉及使用N，N-二甲基乙酰胺二甲基乙缩醛（DMADA）作为羟基的活化剂。使用该方案，可以以高产率到高产率合成具有各种取代基的吡咯烷或哌啶。
• Elevation of HDL cholesterol by 4-&lsqb;(Aminothioxomethyl)-hydrazono&rsqb;-N-(substituted)-4-arylbutanamides
  申请人：American Home Products Corporation

  公开号：US06316467B1

  公开（公告）日：2001-11-13

  Compounds of this invention increase plasma levels of high density lipoprotein or HDL, the “good” cholesterol and as such may be useful for treating diseases such as atherosclerosis. These compounds are represented by the formula wherein: R1, R2, and R3 are independently hydrogen, C1-C6 alkyl, phenyl or —(CH2)1-6 phenyl where phenyl is optionally substituted by halogen, cyano, nitro, C1-C6 alkyl, C1-C6alkoxy, trifluoromethyl, C1-C6 alkoxycarbonyl, —CO2H or OH; R4 and R5 are independently hydrogen, C1-C10 alkyl, C3-C8 cycloalkyl, —(CH2)0-6Ar1 where Ar1 is phenyl, naphthyl, furanyl, pyridinyl or thenyl and Ar1 can be optionally substituted by halogen, cyano, nitro, C1-C6 alkyl, phenyl, C1-C6 alkoxy, phenoxy, trifluoromethyl, C1-C6 alkoxycarbonyl, —CO2H or OH, or R4 and R5 together with the nitrogen to which R4 and R5 are attached form a ring containing 4-7 carbon atoms; and Ar is phenyl, naphthyl, furanyl, pyridinyl or thienyl which may be optionally substituted by halogen, cyano, nitro, C1-C6 alkyl, C3-C6 cycloalkyl, phenyl, C1-C6 alkoxy, phenoxy, trifluoromethyl, C1-C6 alkoxycarbonyl, —CO2H or OH.

  本发明的化合物可以增加高密度脂蛋白或HDL的血浆水平，即“好”胆固醇，因此可用于治疗动脉粥样硬化等疾病。这些化合物的表示式如下：其中：R1、R2和R3独立地为氢、C1-C6烷基、苯基或—（CH2）1-6苯基，其中苯基可以被卤素、氰基、硝基、C1-C6烷基、C1-C6烷氧基、三氟甲基、C1-C6烷氧羰基、—CO2H或OH取代；R4和R5独立地为氢、C1-C10烷基、C3-C8环烷基、—（CH2）0-6Ar1，其中Ar1为苯基、萘基、呋喃基、吡啶基或噻吩基，且Ar1可以被卤素、氰基、硝基、C1-C6烷基、苯基、C1-C6烷氧基、苯氧基、三氟甲基、C1-C6烷氧羰基、—CO2H或OH取代，或者R4和R5与它们连接的氮一起形成一个含有4-7个碳原子的环；Ar为苯基、萘基、呋喃基、吡啶基或噻吩基，可以被卤素、氰基、硝基、C1-C6烷基、C3-C6环烷基、苯基、C1-C6烷氧基、苯氧基、三氟甲基、C1-C6烷氧羰基、—CO2H或OH取代。
• Stereoselective synthesis of 3,4-di-substituted mercaptolactones via photoredox-catalyzed radical addition of thiophenols
  作者：Farzana Kouser、Vijay Kumar Sharma、Masood Rizvi、Shaista Sultan、Neha Chalotra、Vivek K. Gupta、Utpal Nandi、Bhahwal Ali Shah

  DOI：10.1016/j.tetlet.2018.04.046

  日期：2018.5

  A visible light mediated radical addition of thiophenols on 4-phenylbut-3-enoic acids to give diastereoselective synthesis of 3,4-disubstituted γ-lactones is reported. The reaction precludes the conventional prerequisite of conjugate addition. Furthermore, the lactones were successfully utilized in the synthesis of γ-ketoamides.

  报道了在4-苯基丁-3-烯酸上可见光介导的苯酚的自由基加成，以非对映选择性合成3,4-二取代的γ-内酯。该反应排除了缀合物添加的常规先决条件。此外，内酯已成功用于γ-酮酰胺的合成。