1-戊基-1H-吲哚 | 59529-21-4

• 物质功能分类: 医药中间体 - 吲哚类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-戊基-1H-吲哚
• 英文名称: 1-pentyl-1H-indole
• 英文别名: 1-pentylindole；N-pentylindole
• CAS: 59529-21-4
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: QWLCOOAYMQWDPR-UHFFFAOYSA-N

物化性质

• 沸点：
  110-113 °C(Press: 2 Torr)
• 密度：
  0.96±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  1-戊基-1H-吲哚 在 lithium aluminium tetrahydride 、 ammonium acetate 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 16.25h， 生成 (+/-)-1-(1-n-amylindol-3-yl)-2-aminopropane
  参考文献：
  名称：

  Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region

  摘要：

  Taking advantage of a proposed hydrophobic region on 5-HT2 receptors previously identified by radioligand-binding studies utilizing various phenylisopropylamine derivatives, we prepared and evaluated several N1 - and/or C7-alkyl-substituted derivatives of alpha-methyltryptamine in order to improve its affinity and selectivity. It was determined that substitution of an n-propyl or amyl group has similar effect on affinity regardless of location (i.e., N1 or C7). The low affinity of several N1-alkylpyrroleethylamines suggests that the benzene portion of the alpha-methyltryptamines is necessary for significant affinity. Whereas tryptamine derivatives generally display little selectivity for the various populations of 5-HT receptors, N1-n-propyl-5-methoxy-alpha-methyltryptamine (3h) binds with significant affinity (Ki = 12 nM) and selectivity at 5-HT2 receptors relative to 5-HT1A (Ki = 7100 nM), 5-HT1B (Ki = 5000 nM), 5-HT1C (Ki = 120 nM), and 5-HT1D (Ki greater than 10,000 nM) receptors. As a consequence, this is the most 5-HT2-selective indolylalkylamine derivative reported to date.

  DOI：

  10.1021/jm00172a016
• 作为产物：
  描述：

  吲哚 以78%的产率得到
  参考文献：
  名称：

  BARCO A.; BENETTI S.; POLLINI G. P., SYNTHESIS , 1976, NO 2, 124-125

  摘要：

  DOI：

文献信息

• Divergent Dehydrogenative Coupling of Indolines with Alcohols
  作者：Xue Jiang、Weijun Tang、Dong Xue、Jianliang Xiao、Chao Wang

  DOI：10.1021/acscatal.6b03667

  日期：2017.3.3

  The dehydrogenative coupling of indolines with alcohols catalyzed by an iridium complex has been achieved to afford both N- and C3-alkylated indoles selectively, by simply changing the addition time of a base additive. The iridacycle catalyst plays multiple roles in these reactions, which dehydrogenates both amines and alcohols and catalyzes the coupling reactions. Mechanistic studies reveal that a

  通过简单地改变基础添加剂的添加时间，已经实现了二氢吲哚与被铱络合物催化的醇的脱氢偶联，从而选择性地提供了N-和C3-烷基化的吲哚。iridacycle催化剂在这些反应中起多种作用，使胺和醇都脱氢并催化偶联反应。机理研究表明，借用氢-脱氢过程和脱氢-借入氢过程分别涉及N-烷基化和C3-烷基化反应。C3-烷基化反应涉及两个sp3碳中心的直接偶联。
• Iridium- and Rhodium-Catalyzed Directed C–H Heteroarylation of Benzaldehydes with Benziodoxolone Hypervalent Iodine Reagents
  作者：Erwann Grenet、Jérôme Waser

  DOI：10.1021/acs.orglett.8b00337

  日期：2018.3.2

  The C–H heteroarylation of benzaldehydes with indoles and pyrroles was realized using the benziodoxolone hypervalent iodine reagents indole- and pyrroleBX. Functionalization of the aldehyde C–H bond using either an o-hydroxy or amino directing group and catalyzed by an iridium or a rhodium complex allowed the synthesis of salicyloylindoles and (2-sulfonamino)benzoylindoles, respectively, with good

  苯甲醛与吲哚和吡咯的C–H杂芳基化是使用苯并恶唑啉酮高价碘试剂吲哚和吡咯BX实现的。使用邻羟基或氨基直接基团并通过铱或铑络合物催化的醛CH键的功能化可以分别合成水杨基羟吲哚和（2-磺氨基）苯甲酰基吲哚，产率高至优异（74– 98％）。这种新的转化可以在温和的条件下（室温至40°C）进行，并且可以耐受各种功能，例如醚，卤素，羰基或硝基。
• A Gold- and<i>Brønsted</i>Acid Catalytic Interplay Towards the Synthesis of Highly Substituted Tetrahydrocarbazoles
  作者：David Garayalde、Giulia Rusconi、Cristina Nevado

  DOI：10.1002/hlca.201600333

  日期：2017.3

  and stabilized cyclopropyl alkynes under gold‐ and/or gold & Brønsted acid‐catalysis provided access to highly substituted tetrahydrocarbazoles. A mechanistic study revealed the complex mechanism underlying these processes and the opportunistic cooperation of Lewis and Brønsted acid‐catalysts towards the formation of complex molecular scaffolds.

  在金和/或金和布朗斯台德酸催化下，吲哚和稳定的环丙基炔烃的反应提供了获得高度取代的四氢咔唑的途径。机理研究揭示了这些过程背后的复杂机制，以及路易斯和布朗斯台德酸催化剂向复杂分子支架形成的机会合作。
• Friedel–Crafts Fluoroacetylation of Indoles with Fluorinated Acetic Acids for the Synthesis of Fluoromethyl Indol-3-yl Ketones under Catalyst- and Additive-Free Conditions
  作者：Shun-Jiang Yao、Zhi-Hui Ren、Yao-Yu Wang、Zheng-Hui Guan

  DOI：10.1021/acs.joc.6b00580

  日期：2016.5.20

  indoles is reported. The reaction uses fluorinated acetic acids as the fluoroacetylation reagents to synthesize diverse fluoromethyl indol-3-yl ketones in good yields under catalyst- and additive-free conditions. In addition, the only byproduct is water in this transformation. The synthetic utility of this reaction was also demonstrated by the concise synthesis of α-(trifluoromethyl)(indol-3-yl)methanol

  报道了一种简单有效的吲哚氟乙酰化方案。该反应使用氟化乙酸作为氟乙酰化试剂，在无催化剂和无添加剂的条件下以高收率合成了多种氟甲基吲哚-3-基酮。另外，在这种转化中唯一的副产物是水。该反应的合成效用还通过α-（三氟甲基）（吲哚-3-基）甲醇和吲哚-3-羧酸的简明合成来证明。
• Novel indole and azaindole (pyrrolopyridine) cannabinoid (CB) receptor agonists: Design, synthesis, structure–activity relationships, physicochemical properties and biological activity
  作者：Antoni R. Blaazer、Jos H.M. Lange、Martina A.W. van der Neut、Arie Mulder、Femke S. den Boon、Taco R. Werkman、Chris G. Kruse、Wytse J. Wadman

  DOI：10.1016/j.ejmech.2011.08.021

  日期：2011.10

  efforts, several high affinity CB1/CB2 dual cannabinoid receptor ligands were identified. Indole-3-carboxamide 17 displayed single-digit nanomolar affinity and ∼80 fold selectivity for CB1 over the CB2 receptor. The azaindoles displayed substantially improved physicochemical properties (lipophilicity; aqueous solubility). Azaindole 21 elicited potent cannabinoid activity. Cannabinoid receptor agonists 17

  报告了一系列新型的大麻素1（CB 1）和大麻素2（CB 2）受体配体的发现，合成和构效关系（SAR）。基于所述aminoalkylindole类大麻素受体激动剂，联苯部分被引入作为新颖的亲脂性的吲哚3-酰基取代基在11 - 16。此外，系绳是与羧酰胺接头取代-3-羰基17 - 20和氮杂吲哚（吡咯并吡啶）核被设计为具有改进的物理化学性质的吲哚生物电子等排在21 - 25。通过这些SAR努力，几个高亲和力CB 1 / CB 2确定了双重大麻素受体配体。吲哚-3-羧酰胺17对CB 1比CB 2受体具有几位数的纳摩尔亲和力和约80倍的选择性。氮杂吲哚显示出显着改善的理化性质（亲脂性；水溶性）。氮杂吲哚21引起有效的大麻素活性。大麻素受体激动剂17和21在大麻素受体调节的神经传递的急性大鼠脑切片模型中有效地调节了兴奋性突触传递。