phenethyl-carbamic acid prop-2-ynyl ester

• 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: phenethyl-carbamic acid prop-2-ynyl ester
• 英文别名: prop-2-ynyl N-(2-phenylethyl)carbamate
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: MULHXXDRYQJXJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenethyl-carbamic acid prop-2-ynyl ester 在 三甲基氯硅烷 、 三氯一茂钛 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以99%的产率得到2-苯乙胺
  参考文献：
  名称：

  烯丙基和炔丙基氨基甲酸酯的低价钛催化脱保护成胺

  摘要：

  在Me 3 SiCl的存在下，Ti（O- i- Pr）4 / Mg和CpTiCl 3 / Mg试剂可在室温下于室温下有效催化烯丙氧羰基（alloc）和炔丙基氧羰基（poc）保护的胺的脱保护。以高收率生产母体胺。通过Ti（O- i- Pr）4 / Me 3 SiCl / Mg试剂催化的反应，将对Alloc和poc保护的仲胺平滑地脱保护为母体胺。CpTiCl 3 / Me 3 SiCl / Mg试剂成功催化了分配基和poc保护的伯胺的脱保护。

  DOI：

  10.1016/j.tetlet.2016.03.093
• 作为产物：
  描述：

  炔丙基氯甲酸酯 、 2-苯乙胺 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以32%的产率得到phenethyl-carbamic acid prop-2-ynyl ester
  参考文献：
  名称：

  Synthesis of multivalent lactose derivatives by 1,3-dipolar cycloadditions: selective galectin-1 inhibition

  摘要：

  Acetylene derivatives of phenylalanine, phenethylamine and the multifunctional unnatural amino acids, phenyl-bis-alanine and phenyl-tris-alanine, were synthesized and functionalized with 2-azidoethyl beta-D-galactopyranosyl-(1 -> 4)-beta-D-glucopyranoside via regioselective copper(I)-mediated 1,3-dipolar cycloaddition to give a panel of mono-, di- and trivalent lactoside derivatives. Evaluation of the compounds as inhibitors against the tumour- and inflammation-related galectin-1, -3, 4N, 4C, -4, -7, -8N and -9N revealed a divalent compound with a K-d value as low as 3.2 mu M for galectin-1, which corresponded to a relative potency of 30 per lactose unit as compared to the natural disaccharide ligand lactose. This divalent compound had at least one order of magnitude higher affinity for galectin-1 than for any of the other galectins investigated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.028

文献信息

• Highly Efficient Synthesis of Ureas and Carbamates from Amides by Iodosylbenzene-Induced Hofmann Rearrangement
  作者：Peng Liu、Zhiming Wang、Xianming Hu

  DOI：10.1002/ejoc.201101784

  日期：2012.4

  A simple and efficient method for the synthesis of 1,3-disubstituted ureas and carbamates from amides by using iodosylbenzene as the oxidant is described. Symmetric and asymmetric ureas and carbamates can be prepared by this procedure in up to 98 % yield. Ureidopeptides can also be prepared in good yield by this method.

  描述了一种使用碘代苯作为氧化剂从酰胺合成 1,3-二取代脲和氨基甲酸酯的简单有效的方法。对称和不对称尿素和氨基甲酸酯可以通过该程序以高达 98% 的产率制备。通过该方法也可以以良好的产率制备脲肽。
• Low-valent titanium-catalyzed deprotection of allyl- and propargyl-carbamates to amines
  作者：Suchithra Madhavan、Hiromasa Takagi、Shunpei Fukuda、Sentaro Okamoto

  DOI：10.1016/j.tetlet.2016.03.093

  日期：2016.5

  effectively catalyzed the deprotection of allyloxycarbonyl (alloc)- and propargyloxycarbonyl (poc)-protected amines in THF at around room temperature to produce parent amines in good yields. Alloc- and poc-protected secondary amines were smoothly deprotected to parent amines by a reaction catalyzed by a Ti(O-i-Pr)4/Me3SiCl/Mg reagent. The deprotection of alloc- and poc-protected primary amines was successfully

  在Me 3 SiCl的存在下，Ti（O- i- Pr）4 / Mg和CpTiCl 3 / Mg试剂可在室温下于室温下有效催化烯丙氧羰基（alloc）和炔丙基氧羰基（poc）保护的胺的脱保护。以高收率生产母体胺。通过Ti（O- i- Pr）4 / Me 3 SiCl / Mg试剂催化的反应，将对Alloc和poc保护的仲胺平滑地脱保护为母体胺。CpTiCl 3 / Me 3 SiCl / Mg试剂成功催化了分配基和poc保护的伯胺的脱保护。
• Synthesis of multivalent lactose derivatives by 1,3-dipolar cycloadditions: selective galectin-1 inhibition
  作者：Johan Tejler、Erik Tullberg、Torbjörn Frejd、Hakon Leffler、Ulf J. Nilsson

  DOI：10.1016/j.carres.2006.04.028

  日期：2006.7

  Acetylene derivatives of phenylalanine, phenethylamine and the multifunctional unnatural amino acids, phenyl-bis-alanine and phenyl-tris-alanine, were synthesized and functionalized with 2-azidoethyl beta-D-galactopyranosyl-(1 -> 4)-beta-D-glucopyranoside via regioselective copper(I)-mediated 1,3-dipolar cycloaddition to give a panel of mono-, di- and trivalent lactoside derivatives. Evaluation of the compounds as inhibitors against the tumour- and inflammation-related galectin-1, -3, 4N, 4C, -4, -7, -8N and -9N revealed a divalent compound with a K-d value as low as 3.2 mu M for galectin-1, which corresponded to a relative potency of 30 per lactose unit as compared to the natural disaccharide ligand lactose. This divalent compound had at least one order of magnitude higher affinity for galectin-1 than for any of the other galectins investigated. (c) 2006 Elsevier Ltd. All rights reserved.