3-n-propyl-1-hexyne | 900865-50-1

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 3-n-propyl-1-hexyne
• 英文别名: 3-propyl-hex-1-yne；4-Ethynylheptane；4-ethynylheptane
• CAS: 900865-50-1
• 化学式: C₉H₁₆
• 分子量: 124.226
• InChiKey: OIEYWUGXWUYKJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-n-propyl-1-hexyne 在 4-二甲氨基吡啶 、 正丁基锂 、 二甲基硫 、 三氟化硼乙醚 、 氯化二乙基铝 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 1-[5'-(1-hydroxy-5-propyl-oct-3-ynyl)-octahydro-[2,2']bifuranyl-5-yl]-5-propyl-oct-3-yn-1-ol
  参考文献：
  名称：

  Function of the alkyl side chains of Δlac-acetogenins in the inhibitory effect on mitochondrial complex I (NADH-ubiquinone oxidoreductase)

  摘要：

  We synthesized a series of Alac-acetogenins in which the two alkyl side chains were systematically modified, and examined their inhibitory effect on bovine heart mitochondrial complex I (NADH-ubiquinone oxidoreductase). The results revealed that the physicochemical properties of the side chains, such as the balance of hydrophobicity and the width (or bulkiness) of the chains, are important structural factors for a potent inhibitory effect of amphiphilic Alac-acetogenins. This is probably because such properties decide the precise location of the hydrophilic bis-THF ring moiety in the enzyme embedded in the inner mitochondrial membrane. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.082
• 作为产物：
  描述：

  2-丙基-1-戊醇 在 正丁基锂 、 三苯基膦 作用下， 生成 3-n-propyl-1-hexyne
  参考文献：
  名称：

  Function of the alkyl side chains of Δlac-acetogenins in the inhibitory effect on mitochondrial complex I (NADH-ubiquinone oxidoreductase)

  摘要：

  We synthesized a series of Alac-acetogenins in which the two alkyl side chains were systematically modified, and examined their inhibitory effect on bovine heart mitochondrial complex I (NADH-ubiquinone oxidoreductase). The results revealed that the physicochemical properties of the side chains, such as the balance of hydrophobicity and the width (or bulkiness) of the chains, are important structural factors for a potent inhibitory effect of amphiphilic Alac-acetogenins. This is probably because such properties decide the precise location of the hydrophilic bis-THF ring moiety in the enzyme embedded in the inner mitochondrial membrane. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.082

文献信息

• A new reaction of 1-bromoalk-1-ynes; synthesis of 3-alkylalk-1-ynes from terminal acetylenes
  作者：Augustus J. Quillinan、Ejaz A. Khan、Feodor Scheinmann

  DOI：10.1039/c39740001030

  日期：——

  The reaction of 1-bromoalk-1-ynes with two equivalents of butyl-lithium in hexane gives 3-butylalk-1-ynes; the reactive intermediate is a dilithioalkyne which can also be directly prepared from terminal acetylenes, and selective reaction with alkyl halides in hexane occurs at the propargylic site to provide a general synthesis of 3-alkylalk-1-ynes.

  1-溴代烷基-1-炔与两当量的丁基锂在己烷中的反应得到3-丁基代烷基-1-炔；反应性中间体是二硫代炔烃，也可以直接从末端乙炔制备，并且在炔丙基位点发生与烷基卤在己烷中的选择性反应，从而提供3-烷基烷-1-炔的一般合成。
• Function of the alkyl side chains of Δlac-acetogenins in the inhibitory effect on mitochondrial complex I (NADH-ubiquinone oxidoreductase)
  作者：Naoya Ichimaru、Masato Abe、Masatoshi Murai、Mai Senoh、Takaaki Nishioka、Hideto Miyoshi

  DOI：10.1016/j.bmcl.2006.03.082

  日期：2006.7

  We synthesized a series of Alac-acetogenins in which the two alkyl side chains were systematically modified, and examined their inhibitory effect on bovine heart mitochondrial complex I (NADH-ubiquinone oxidoreductase). The results revealed that the physicochemical properties of the side chains, such as the balance of hydrophobicity and the width (or bulkiness) of the chains, are important structural factors for a potent inhibitory effect of amphiphilic Alac-acetogenins. This is probably because such properties decide the precise location of the hydrophilic bis-THF ring moiety in the enzyme embedded in the inner mitochondrial membrane. (c) 2006 Elsevier Ltd. All rights reserved.