1-[(4-乙烯基苯基)甲基]哌嗪 | 168270-38-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-[(4-乙烯基苯基)甲基]哌嗪
• 英文名称: 1-(4-vinylbenzyl)piperazine
• 英文别名: N-(4-vinylbenzyl)piperazine；4-vinylbenzylpiperazine；1-[(4-Ethenylphenyl)methyl]piperazine
• CAS: 168270-38-0
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: ADHMJVLPJMDBLH-UHFFFAOYSA-N

物化性质

• 沸点：
  316.7±27.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(4-乙烯基苯基)甲基]哌嗪 在 碳酸氢钠 、 肼 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 2-(4-(4-ethylbenzyl)piperazin-1-yl)acetohydrazide
  参考文献：
  名称：

  Parallel Synthesis and Biological Evaluation of 837 Analogues of Procaspase-Activating Compound 1 (PAC-1)

  摘要：

  Procaspase-Activating Compound 1 (PAC-1) is an ortho-hydroxy N-acyl hydrazone that enhances the enzymatic activity of procaspase-3 in vitro and induces apoptosis in cancer cells. An analogue of PAC-1, called S-PAC-1, was evaluated in a veterinary clinical trial in pet dogs with lymphoma and found to have considerable potential as an anticancer agent. With the goal of identifying more potent compounds in this promising class of experimental therapeutics, a combinatorial library based on PAC-1 was created, and the compounds were evaluated for their ability to induce death of cancer cells in culture. For library construction, 31 hydrazides were condensed in parallel with 27 aldehydes to create 837 PAC-1 analogues, with an average purity of 91%. The compounds were evaluated for their ability to induce apoptosis in cancer cells, and through this work, six compounds were discovered to be substantially more potent than PAC-1 and S-PAC-1. These six hits were further evaluated for their ability to relieve zinc-mediated inhibition of procaspase-3 in vitro. In general, the newly identified hit compounds are two- to four-fold more potent than PAC-1 and S-PAC-1 in cell culture, and thus have promise as experimental therapeutics for treatment of the many cancers that have elevated expression levels of procaspase-3.

  DOI：

  10.1021/co2001372
• 作为产物：
  描述：

  哌嗪 、 4-氯甲基苯乙烯 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 1-[(4-乙烯基苯基)甲基]哌嗪
  参考文献：
  名称：

  Organocatalytic Decarboxylative Doebner-Knoevenagel Reactions between Arylaldehydes and Monoethyl Malonate Mediated by a Bifunctional Polymeric Catalyst

  摘要：

  一种双功能聚苯乙烯被制备出来，具有DMAP和哌啶基团，并被用作芳醛和单乙酯丙二酸的脱羧Doebner-Knoevenagel反应的有机催化剂。所得到的肉桂酸酯的分离收率非常高，并且在所有情况下仅检测到E-异构体。当仅使用功能化为DMAP或哌啶基团的聚苯乙烯催化剂进行这些反应时，催化效果明显不如双功能聚苯乙烯。此外，使用单功能聚合物的组合进行催化的效率也低于双功能聚苯乙烯。因此，似乎通过将两种不同的催化胺基团共同定位在同一聚合物主链上，可以获得协同效应。

  DOI：

  10.1055/s-0030-1260808

文献信息

• PROCASPASE-ACTIVATING COMPOUNDS AND COMPOSITIONS
  申请人：The Board of Trustees of the University of Illinoi

  公开号：US20130096133A1

  公开（公告）日：2013-04-18

  The invention provides compounds and compositions useful for the modulation of certain enzymes. The compounds and compositions can induce of cell death, particularly cancer cell death. The invention also provides methods for the synthesis and use of the compounds and compositions, including the use of compounds and compositions in therapy for the treatment of cancer and selective induction of apoptosis in cells.

  这项发明提供了用于调节某些酶的化合物和组合物。这些化合物和组合物可以诱导细胞死亡，特别是癌细胞死亡。该发明还提供了合成和使用这些化合物和组合物的方法，包括在治疗癌症和选择性诱导细胞凋亡中使用这些化合物和组合物的方法。
• [EN] ENZYME-ACTIVATING COMPOUNDS AND COMPOSITIONS<br/>[FR] COMPOSÉS ET COMPOSITIONS ACTIVANT DES ENZYMES
  申请人：HERGENROTHER PAUL J

  公开号：WO2014022858A1

  公开（公告）日：2014-02-06

  The invention provides compounds and compositions useful for the modulation of certain enzymes. The compounds and compositions can induce of cell death, particularly cancer cell death. The invention also provides methods for the synthesis and use of the compounds and compositions, including the use of compounds and compositions in therapy for the treatment of cancer and selective induction of apoptosis in cells.

  这项发明提供了用于调节某些酶的化合物和组合物。这些化合物和组合物可以诱导细胞死亡，特别是癌细胞死亡。该发明还提供了合成和使用这些化合物和组合物的方法，包括在治疗癌症和选择性诱导细胞凋亡中使用这些化合物和组合物的方法。
• Polystyrenes with chiral phosphoramide substituents as Lewis base catalysts for asymmetric addition of allyltrichlorosilane: enhancement of catalytic performance by polymer effect
  作者：Toshiyuki Oyama、Hiroki Yoshioka、Masao Tomoi

  DOI：10.1039/b417311b

  日期：——

  In the asymmetric addition of allyltrichlorosilane to benzaldehyde, polystyrenes with chiral phosphoramide substituents as Lewis base catalysts showed up to 2.4 times better catalytic activity and 1.4 times higher enantioselectivity than the corresponding low-molecular-weight analogues.

  在烯丙基三氯硅烷与苯甲醛的不对称加成反应中，具有手性磷酰胺取代基的聚苯乙烯作为路易斯碱催化剂，其催化活性比相应的低分子量类似物高出2.4倍，选择性优异性高出1.4倍。
• Organocatalytic Decarboxylative Doebner-Knoevenagel Reactions between Arylaldehydes and Monoethyl Malonate Mediated by a Bifunctional Polymeric Catalyst
  作者：Patrick Toy、Jinni Lu

  DOI：10.1055/s-0030-1260808

  日期：2011.7

  A bifunctional polystyrene bearing both DMAP and piperidine groups has been prepared and used as an organocatalyst for decarboxylative Doebner-Knoevenagel reactions of arylaldehydes and monoethyl malonate. Isolated yields of the resulting cinnamates were very high, and in all cases only the E-isomer was detected. When a polystyrene catalyst functionalized with only DMAP or piperidine groups was used in these reactions, catalysis was much less efficient. Furthermore, catalysis using a combination of the monofunctional polymers was also less efficient than with the bifunctional polystyrene. Thus, it appears that there is a synergistic effect obtained by co-locating the two different catalytic amine groups on the same polymer backbone.

  一种双功能聚苯乙烯被制备出来，具有DMAP和哌啶基团，并被用作芳醛和单乙酯丙二酸的脱羧Doebner-Knoevenagel反应的有机催化剂。所得到的肉桂酸酯的分离收率非常高，并且在所有情况下仅检测到E-异构体。当仅使用功能化为DMAP或哌啶基团的聚苯乙烯催化剂进行这些反应时，催化效果明显不如双功能聚苯乙烯。此外，使用单功能聚合物的组合进行催化的效率也低于双功能聚苯乙烯。因此，似乎通过将两种不同的催化胺基团共同定位在同一聚合物主链上，可以获得协同效应。
• [EN] METHOD FOR PREPARING TERTIARY AMINES COMPRISING ETHYNYLBENZYL SUBSTITUENTS<br/>[FR] PROCÉDÉ DE PRÉPARATION D'AMINES TERTIAIRES COMPRENANT DES SUBSTITUANTS ÉTHYNYLBENZYLE
  申请人：SIBUR HOLDING PUBLIC JOINT STOCK CO

  公开号：WO2017116272A1

  公开（公告）日：2017-07-06

  The invention relates to the field of the organic chemistry and, in particular to a method for preparing a compound of formula (I) or (II), and/or a mixture of isomers thereof, wherein R is -Alk, -AlkN(Alk)2, -AlkN(Ar)2, -AlkNAlkAr, -AlkOH, -AlkOAlk, -AlkOAr, -AlkSAlk, -AlkSAr, or -Ar; R1, R2, R3, and R4 are independently -Alk, -Hal, - OH, -OAlk, -OAr, -SAlk, -SAr, or -NR2, wherein R is -Alk, - AlkN(Alk)2, -AlkN(Ar)2, -AlkNAlkAr, -AlkOH, -AlkOAlk, -AlkOAr, -AlkSAlk, -AlkSAr, or -Ar, wherein Alk is C1- C16alkyl, C3-C16cycloalkyl, C2-C16alkenyl, C2-C16alkynyl; Ar is phenyl; Hal is halogen selected from -Cl, -Br, and -I,

  该发明涉及有机化学领域，特别是一种制备化合物的方法，该化合物的化学式为(I)或(II)，和/或其异构体混合物，其中R为-Alk，-AlkN(Alk)2，-AlkN(Ar)2，-AlkNAlkAr，-AlkOH，-AlkOAlk，-AlkOAr，-AlkSAlk，-AlkSAr或-Ar；R1、R2、R3和R4独立地为-Alk、-Hal、-OH、-OAlk、-OAr、-SAlk、-SAr或-NR2，其中R为-Alk、-AlkN(Alk)2、-AlkN(Ar)2、-AlkNAlkAr、-AlkOH、-AlkOAlk、-AlkOAr、-AlkSAlk、-AlkSAr或-Ar，其中Alk为C1-C16烷基，C3-C16环烷基，C2-C16烯基，C2-C16炔基；Ar为苯基；Hal为从-Cl，-Br和-I中选择的卤素。