N-[4-(三甲基硅烷基)-3-丁炔基]-乙酰胺 | 183208-72-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-[4-(三甲基硅烷基)-3-丁炔基]-乙酰胺
• 中文别名: 3-(N,N-二乙胺基)-L-丙氨酸
• 英文名称: N-[4-(1,1,1-trimethylsilyl)-3-butyn-1-yl]acetamide
• 英文别名: 4-trimethylsilylbut-3-ynylacetamide；N-[4-(1,1,1-trimethylsilyl)-3-butynyl]acetamide；N-(4-trimethylsilylbut-3-ynyl)acetamide
• CAS: 183208-72-2
• 化学式: C₉H₁₇NOSi
• 分子量: 183.326
• InChiKey: JDGWHYHCAOIXOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  4-(三甲基甲硅烷基)丁-3-炔-1-胺	4-(trimethylsilyl)but-3-yn-1-amine	183208-71-1	C7H15NSi	141.288

反应信息

• 作为反应物：
  描述：

  N-[4-(三甲基硅烷基)-3-丁炔基]-乙酰胺 在 钯 氧气 、 copper dichloride 作用下， 以 盐酸 、 乙腈 为溶剂， 反应 24.0h， 以40%的产率得到1-乙酰-2-吡咯烷酮
  参考文献：
  名称：

  Palladium(II)-mediated oxidative cyclization of N-carbamoyl aminoalkynes: a new route to γ-lactams

  摘要：

  DOI：

  10.1016/s0040-4039(99)01305-2
• 作为产物：
  描述：

  4-(三甲基甲硅烷基)丁-3-炔-1-胺 在 乙酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-[4-(三甲基硅烷基)-3-丁炔基]-乙酰胺
  参考文献：
  名称：

  Virtual screening-driven discovery of dual 5-HT6/5-HT2A receptor ligands with pro-cognitive properties

  摘要：

  A virtual screening campaign aimed at finding structurally new compounds active at 5-HT6R provided a set of candidates. Among those, one structure, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl) amino]methyl}furan-2-yl)phenol (1, 5-HT6R K-i = 91 nM), was selected as a hit for further optimization. As expected, the chemical scaffold of selected compound was significantly different from all the serotonin receptor ligands published to date. Synthetic efforts, supported by molecular modelling, provided 43 compounds representing different substitution patterns. The derivative 42, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl)amino]methyl}furan-2-yl)phenol (5-HT6R K-j= 25, 5-HT2AR K-i = 32 nM), was selected as a lead and showed a good brain/plasma concentration profile, and it reversed phencyclidine-induced memory impairment. Considering the unique activity profile, the obtained series might be a good starting point for the development of a novel antipsychotic or antidepressant with procognitive properties. (C) 2019 The Authors. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.111857

文献信息

• Aza-Tryptamine Substrates in Monoterpene Indole Alkaloid Biosynthesis
  作者：Hyang-Yeol Lee、Nancy Yerkes、Sarah E. O'Connor

  DOI：10.1016/j.chembiol.2009.11.016

  日期：2009.12

  as the starting substrate for a variety of alkaloid biosynthetic pathways, by replacing the indole with one of four aza-indole isomers. We show that two aza-tryptamine substrates can be successfully incorporated into the products of the monoterpene indole alkaloid pathway inCatharanthus roseus. Use of unnatural heterocycles in precursor-directed biosynthesis, in both microbial and plant natural product pathways

  通过引入新的起始材料，可以劫持生物合成途径以产生新的化合物。在这里，我们通过用四种氮杂吲哚异构体之一替换吲哚来改变色胺，色胺是各种生物碱生物合成途径的起始底物。我们表明两种氮杂色胺底物可以成功地掺入长春花中单萜吲哚生物碱途径的产物中。非天然杂环在微生物和植物天然产物途径中的前体导向生物合成中的使用尚未得到广泛证明，并且先前未报道过成功掺入含有氮杂吲哚官能团的起始底物类似物。
• 5-ZATRYPTAMINE ANALOGS AS h5-HT6 SEROTONIN RECEPTOR LIGANDS
  作者：Manik Pullagurla、Małgorzata Dukat、Bryan L. Roth、Vincent Setola、Richard A. Glennon

  DOI：10.1007/s00044-004-0121-8

  日期：2005.1

  5-Aza analogs were prepared of several tryptamine derivatives and a skatole derivative known to bind at human 5-HT6 receptors and evaluated to determine if they bind in a manner similar to their indolic analogs. In general, the azatryptamines did not behave exactly like their tryptamine counterparts, but the behavior of NI-benzenesulfonyl analogs was reminiscent of the known arylsulfonyltryptamines. For example, N-1-(4-aminobenzenesulfonyl)-5-azaskatole (18; K-i = 41 nM) displayed an affinity comparable to N-1-(4-aminobenzenesulfonyl)skatole.
• Microwave-assisted synthesis of 5-carboxymethoxy- N -acetyltryptamine derivatives
  作者：Adriana Fı̂naru、Aurélie Berthault、Thierry Besson、Gérald Guillaumet、Sabine Berteina-Raboin

  DOI：10.1016/s0040-4039(01)02273-0

  日期：2002.1

  The synthesis of the indole core structure was investigated using microwave irradiation. The experimental microwave conditions described allow significant rate enhancements and good yields compared to conventional reaction conditions. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of New Melatoninergic Ligands Including Azaindole Moiety
  作者：Marie-Claude Viaud-Massuard、Daniel Mazéas、Gérald Guillaumet

  DOI：10.3987/com-98-s(h)111

  日期：——
• Microwave-Assisted Solid-Phase Synthesis of 5-Carboxamido-<i>N</i>-acetyltryptamine Derivatives
  作者：Adriana Fînaru、Aurélie Berthault、Thierry Besson、Gérald Guillaumet、Sabine Berteina-Raboin

  DOI：10.1021/ol0259185

  日期：2002.8.1

  [GRAPHICS]The synthesis of the indole skeleton of new melatoninergic analogues was realized using solid-phase methodology in association with microwave irradiation. This combination speeds up the solid-phase drug discovery process in rigorously established conditions.