tert-butyl 4-(2H,3H-benzo[e]-1,4-dioxin-6-yl)piperazinecaboxylate | 750573-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: tert-butyl 4-(2H,3H-benzo[e]-1,4-dioxin-6-yl)piperazinecaboxylate
• 英文别名: Tert-butyl 4-(2,3-dihydro-1,4-benzodioxin-6-yl)piperazine-1-carboxylate
• CAS: 750573-08-1
• 化学式: C₁₇H₂₄N₂O₄
• 分子量: 320.389
• InChiKey: NZIDBQNRHPCAGV-UHFFFAOYSA-N

物化性质

• 沸点：
  464.1±45.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(2H,3H-benzo[e]-1,4-dioxin-6-yl)piperazinecaboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%的产率得到哌嗪,1-(2,3-二氢-1,4-苯并二噁烯-6-基)
  参考文献：
  名称：

  6-(4-Benzylpiperazin-1-yl)benzodioxanes as selective ligands at cloned primate dopamine D4 receptors

  摘要：

  A series of novel 6-(4-benzylpiperazin-1-yl)benzodioxanes were prepared and screened at selected dopamine receptor subtypes. 6-(4-[4-Chlorobenzyl]piperazin-1-yl)benzodioxane (2d) had high affinity and selectivity for the D-4 dopamine receptor subtype and was identified as a D-4 antagonist via its attenuation of dopamine-induced GT gamma S-35 binding at the D-4 receptor. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00226-7
• 作为产物：
  描述：

  6-溴-1,4-苯并恶烷 、 N-Boc-哌嗪 在 三(邻甲基苯基)磷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 生成 tert-butyl 4-(2H,3H-benzo[e]-1,4-dioxin-6-yl)piperazinecaboxylate
  参考文献：
  名称：

  Synthesis of arylpiperazines via palladium-catalysed aromatic amination reactions of bromoarenes with N-tert-butoxycarbonylpiperazine

  摘要：

  Reaction of a series of bicyclic bromoarenes with N-tert-butoxycarbonylpiperazine (N-Boc-piperazine) under palladium-calalysed coupling conditions followed by routine removal of the Boc group with trifluoroacetic acid in dichloromethane gave the corresponding arylpiperazines in moderate to good yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00179-8

文献信息

• 6-(4-Benzylpiperazin-1-yl)benzodioxanes as selective ligands at cloned primate dopamine D4 receptors
  作者：Kevin J Hodgetts、Andrzej Kieltyka、Robbin Brodbeck、Jennifer N Tran、Jan W.F Wasley、Andrew Thurkauf

  DOI：10.1016/s0968-0896(01)00226-7

  日期：2001.12

  A series of novel 6-(4-benzylpiperazin-1-yl)benzodioxanes were prepared and screened at selected dopamine receptor subtypes. 6-(4-[4-Chlorobenzyl]piperazin-1-yl)benzodioxane (2d) had high affinity and selectivity for the D-4 dopamine receptor subtype and was identified as a D-4 antagonist via its attenuation of dopamine-induced GT gamma S-35 binding at the D-4 receptor. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of arylpiperazines via palladium-catalysed aromatic amination reactions of bromoarenes with N-tert-butoxycarbonylpiperazine
  作者：Frank Kerrigan、Claire Martin、Gerard H. Thomas

  DOI：10.1016/s0040-4039(98)00179-8

  日期：1998.4

  Reaction of a series of bicyclic bromoarenes with N-tert-butoxycarbonylpiperazine (N-Boc-piperazine) under palladium-calalysed coupling conditions followed by routine removal of the Boc group with trifluoroacetic acid in dichloromethane gave the corresponding arylpiperazines in moderate to good yield. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Discovery of small molecules that inhibit melanogenesis via regulation of tyrosinase expression
  作者：Jiho Song、Hyun-e Lee、Young Jin Kim、Su Yeon Kim、Dong-Seok Kim、Kyung Hoon Min

  DOI：10.1016/j.bmcl.2012.09.003

  日期：2012.11

  5,6,7,8-Tetrahydro-4H-cyclohepta[d]isoxazole derivatives were synthesized and evaluated as a novel class of inhibitors for alpha-melanocyte-stimulating hormone (alpha-MSH) induced melanogenesis in a mouse melanoma B16F10 cell line. Compound 8e (IC50 = 0.67 mu M), 8h (IC50 = 1.01 mu M) and 9b (IC50 = 0.99 mu M) exhibited a potent inhibitory activity approximately 85- to 126-fold greater than kojic acid, a well-known potent inhibitor. A biochemical study indicates that the activity of this series should be displayed via down-regulation of the expression of tyrosinase. (C) 2012 Elsevier Ltd. All rights reserved.