2-isocyano-3-phenyl-1-(piperidin-1-yl)propan-1-one | 85059-38-7

• 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: 2-isocyano-3-phenyl-1-(piperidin-1-yl)propan-1-one
• 英文别名: Piperidine, 1-(2-isocyano-1-oxo-3-phenylpropyl)-；2-isocyano-3-phenyl-1-piperidin-1-ylpropan-1-one
• CAS: 85059-38-7
• 化学式: C₁₅H₁₈N₂O
• 分子量: 242.321
• InChiKey: UFZUARSQMXJQBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-isocyano-3-phenyl-1-(piperidin-1-yl)propan-1-one 在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 2,7-Dibenzyl-8-hexyl-3-piperidin-1-yl-5,6,7,8-tetrahydro-[1,7]naphthyridine-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Multicomponent synthesis of epoxy-tetrahydronaphthyridine and structural diversification by subsequent fragmentation

  摘要：

  Three-component reaction of an alpha-isocyanoacetamide 7, an homoallylamine 8 and an aldehyde 9 in methanol at room temperature provides oxa-bridged tricycle 4 in good to excellent yield as a mixture of two separable diastereoisomers. In this one-pot multicomponent process, one C-N, one C-O and three C-C bonds are formed with concomitant creation of five asymmetric centers and three rings. Fragmentation of epoxy-tetrahydronaphthyridine 4 affords differentially substituted 5,6,7,8-tetrahydro-1,7-naphthyridine (5, 6) depending on the reaction conditions, providing thus additional structural diversity. A one-pot three-component synthesis of 5,6,7,8-tetrahydro-1,7-'naphthyridine (6) from 7, 8 and 9 is also documented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.017
• 作为产物：
  描述：

  N-甲酰基-DL-苯丙氨酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 2-isocyano-3-phenyl-1-(piperidin-1-yl)propan-1-one
  参考文献：
  名称：

  通过异氰酸酯对内消旋氮丙啶的不对称化发散合成对映体富集的β-功能胺

  摘要：

  在手性N，N'-二氧化物/ Mg（OTf）2络合物的存在下，内消旋氮杂环丁烷与异氰酸酯的高度对映选择性开环脱对称。原位产生的手性1,4-两性离子中间体被分子内基于氧和碳的亲核试剂或外源H 2 O和TMSN 3成功捕获，从而可以合成各种手性邻位氨基恶唑，螺二氢吲哚和β-氨基酰胺和四唑衍生物，具有中等至高收率，具有出色的对映选择性。

  DOI：

  10.1021/acs.orglett.9b02242

文献信息

• Palladium-Catalyzed Imidoylative Cyclization of α-Isocyanoacetamides: Efficient Access to C2-Diversified Oxazoles
  作者：Jian Wang、Shuang Luo、Jinbo Huang、Tingting Mao、Qiang Zhu

  DOI：10.1002/chem.201403033

  日期：2014.8.25

  A novel procedure for the synthesis of C2‐diversified oxazoles, through palladium‐catalyzed imidoylative cyclization of α‐isocyanoacetamides with aryl, vinyl, alkynyl halides, or triflates, was developed. Migratory insertion of isocyanide into a C‐palladium(II) intermediate in a cascade process was also realized, generating alkyl‐substituted oxazoles. Therefore, oxazoles functionalized at the C2 position

  通过钯催化α-异氰基乙酰胺与芳基，乙烯基，炔基卤化物或三氟甲磺酸酯的亚胺基化环化反应，开发了一种新颖的合成C2恶唑的方法。还实现了在级联过程中将异氰酸酯迁移插入C-钯（II）中间体中，生成烷基取代的恶唑。因此，可通过应用此方法获得在C2位置被sp，sp 2和sp 3杂化的碳原子官能化的恶唑。
• Synthesis of Polyheterocyclic Pyrrolo[3,4-b]pyridin-5-ones via a One-Pot (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2) Process. A Suitable Alternative towards Novel Aza-Analogues of Falipamil
  作者：Angel Zamudio-Medina、Ailyn García-González、Genesis Herrera-Carrillo、Daniel Zárate-Zárate、Adriana Benavides-Macías、Joaquín Tamariz、Ilich Ibarra、Alejandro Islas-Jácome、Eduardo González-Zamora

  DOI：10.3390/molecules23040763

  日期：——

  We describe the one-pot synthesis of twenty polyheterocyclic pyrrolo[3,4-b]pyridin-5-ones via a cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization) in 20 to 95% overall yields, as well as four pharmacologically promising analogues via an improved cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2): two piperazine-linked pyrrolo[3,4-b]pyridin-5-ones in 33 and 34%

  我们描述了通过级联过程（Ugi-3CR / Aza Diels-Alder / N-酰化/芳构化）以20％至95％的总产率一锅合成二十个多杂环吡咯并[3,4-b]吡啶基-5-酮，以及通过改进的级联过程（Ugi-3CR / Aza Diels-Alder / N-酰化/芳香化/ SN2）得到的四个在药理上有希望的类似物：两个哌嗪连接的吡咯并[3,4-b]吡啶-5-酮33％和34％，以及几个Falipamil氮杂类似物，总产率为30％和35％。值得一提的是，发现了良好的底物范围，因为最终产品配有烷基，芳基和杂环取代基。使用链环可互变异构异氰酸酯（作为Ugi型三组分反应的关键试剂）可以快速有效地组装多取代的羟吲哚，这些化合物原位用于复杂的产品，
• 1,6-Addition Arylation of para-Quinone Methides: An Approach to Unsymmetrical Triarylmethanes
  作者：Shang Gao、Xiuyan Xu、Zhenbo Yuan、Haipin Zhou、Hequan Yao、Aijun Lin

  DOI：10.1002/ejoc.201600385

  日期：2016.6

  A 1,6-addition arylation reaction of para-quinone methides with α-isocyanoacetamides and electron-rich aromatic compounds under metal-free conditions has been developed. BF3·Et2O plays two roles in the reaction: catalyzing the cyclization of α-isocyanoacetamides to give oxazoles, and activating the para-quinone methides to achieve the 1,6-addition arylation process. The reaction shows good functional

  已经开发了在无金属条件下对醌甲基化物与 α-异氰基乙酰胺和富电子芳族化合物的 1,6-加成芳基化反应。BF3·Et2O在反应中起两个作用：催化α-异氰基乙酰胺环化生成恶唑，活化对醌甲基化物以实现1,6-加成芳基化过程。该反应显示出良好的官能团耐受性、可扩展性和区域选择性。它是用于合成各种不对称三芳基甲烷的 consice 协议。所得三芳基甲烷的进一步转化为一些官能化分子提供了有效途径。
• A N,N′-dioxide/Mg(OTf)₂ complex catalyzed enantioselective α-addition of isocyanides to alkylidene malonates
  作者：Weiwei Luo、Xiao Yuan、Lili Lin、Pengfei Zhou、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c6sc00689b

  日期：——

  A simple and efficient catalytic asymmetric [small alpha]-addition of isocyanides to alkylidene malonates was realized using a chiral N,N[prime or minute]-dioxide/MgII catalyst. A variety of 2-alkyl-5-aminoxazoles were obtained in up to 99% yield and 96% ee, and could be converted to imides and dipeptides.

  使用手性N，N [伯或分钟]二氧化物/ Mg II催化剂，可以实现简单有效的异氰酸酯向亚烷基丙二酸酯的催化不对称α-小加成反应。以高达99％的收率和96％的ee获得了各种2-烷基-5-氨基恶唑，并且可以将其转化为酰亚胺和二肽。
• An efficient Ugi-3CR/aza Diels–Alder/Pomeranz–Fritsch protocol towards novel aza-analogues of (±)-nuevamine, (±)-lennoxamine and magallanesine: a diversity oriented synthesis approach
  作者：Óscar Vázquez-Vera、Jorge S. Sánchez-Badillo、Alejandro Islas-Jácome、Manuel A. Rentería-Gómez、Shrikant G. Pharande、Carlos J. Cortes-García、Mónica A. Rincón-Guevara、Ilich A. Ibarra、Rocío Gámez-Montaño、Eduardo González-Zamora

  DOI：10.1039/c6ob02572b

  日期：——

  rapid and efficient synthesis of a series of (±)-nuevamine, (±)-lennoxamine and magallanesine aza analogues is described. The synthetic strategy involves Ugi-3CR and two further condensation processes, aza-Diels–Alder cycloaddition and the Pomeranz–Fritsch reaction. The variation of the chain-size in aldehyde moieties provided structural diversity in only two operational reaction steps.

  描述了一系列（±）-新胺，（±）-伦诺明和麦加丙氨酸氮杂类似物的快速有效合成。合成策略涉及Ugi-3CR和另外两个缩合过程，即aza-Diels-Alder环加成反应和Pomeranz-Fritsch反应。醛基部分链大小的变化仅在两个操作反应步骤中提供了结构多样性。