3-(naphth-1'-ylmethyl)-1-pentyl-1H-indole | 619294-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(naphth-1'-ylmethyl)-1-pentyl-1H-indole
• 英文别名: 3-(1-naphthalenylmethyl)-1-pentyl-1H-indole；3-(Naphthalen-1-ylmethyl)-1-pentylindole
• CAS: 619294-35-8
• 化学式: C₂₄H₂₅N
• 分子量: 327.469
• InChiKey: TYBRSILIYTUTSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  505.6±19.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：20mg/mL； DMSO：20mg/mL；乙醇：20mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-(naphth-1'-ylmethyl)-1-pentyl-1H-indole 在 亚硝酸特丁酯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以52%的产率得到1-戊基-3-(1-萘甲酰基)吲哚
  参考文献：
  名称：

  具有3DDQ * /叔丁基亚硝酸盐共催化系统的可见光光催化好氧苯甲酸C（sp3）-H氧合

  摘要：

  通过使用3 DDQ *（DDQ = 2,3-dichloro-5,6-dicyanoano，1,4的共催化系统）研究了芳烃和C3取代的吲哚的光催化好氧苄基C（sp 3）-H氧化苯醌）和亚硝酸叔丁酯。通过与类似的热方案进行比较，证明了这些反应条件的优异效率，并且可以以良好的收率催化和选择性地氧化多种底物。

  DOI：

  10.1002/cctc.201600704
• 作为产物：
  描述：

  3-(1-萘甲酰基)吲哚 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 生成 3-(naphth-1'-ylmethyl)-1-pentyl-1H-indole
  参考文献：
  名称：

  Synthesis, cytotoxicity and QSAR studies of indolic cannabinoid-triazole hybrids

  摘要：

  DOI：

  10.1016/j.molstruc.2023.135889

文献信息

• Tandem Organocatalysis and Photocatalysis: An Anthraquinone‐Catalyzed Indole‐C3‐Alkylation/Photooxidation/1,2‐Shift Sequence
  作者：Stephanie Lerch、Lisa‐Natascha Unkel、Malte Brasholz

  DOI：10.1002/anie.201402920

  日期：2014.6.16

  the development of sequential catalytic processes. Herein, the discovery of an anthraquinone‐catalyzed thermal indole‐C3‐alkylation with benzylamines is described, which can be combined sequentially with a new visible‐light‐driven catalytic photooxidation/1,2‐shift reaction. The one‐flask tandem process converts indoles into 3‐benzylindole intermediates, which are further transformed into new fluorescent

  醌具有正交的基态和激发态反应性，因此非常适合用于开发顺序催化过程的有机催化剂。本文描述了蒽醌催化的热吲哚-C3-烷基苄胺的发现，该发现可与新的可见光驱动的催化光氧化/ 1,2-转移反应相结合。单烧瓶串联过程将吲哚转化为3-苄基吲哚中间体，然后将其进一步转化为新的2,2-二取代的吲哚啉-3-酮荧光衍生物。
• 3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB1 cannabinoid receptor
  作者：John W Huffman、Ross Mabon、Ming-Jung Wu、Jianzhong Lu、Richard Hart、Dow P Hurst、Patricia H Reggio、Jenny L Wiley、Billy R Martin

  DOI：10.1016/s0968-0896(02)00451-0

  日期：2003.2

  A series of 1-pentyl-1H-indol-3-yl-(1-naphthyl)methanes (9 11) and 2-methyl-1-pentyl-1H-indol-3-yl-(1-naphthyl)methanes (12-14) have been synthesized to investigate the hypothesis that cannabimimetic 3-(1-naphthoyl)indoles interact with the CB I receptor by hydrogen bonding to the carbonyl group. Indoles 9-11 have significant (K-i 17-23 nM) receptor affinity, somewhat less than that of the corresponding naphthoylindoles (5, 15, 16). 2-Methyl-1-indoles 12-14 have little affinity for the CB1 receptor, in contrast to 2-methyl-3-(1-naphthoyl)indoles 17-19, which have affinities comparable to those of 5, 15, 16. A cannabimimetic indene hydrocarbon (26) was synthesized and found to have K-i = 26 +/- 4 nM. Molecular modeling and receptor docking studies of naphthoylindole 16, its 2-methyl congener (19) and indolyl-1-naphthylmethanes 11 and 14, combined with the receptor affinities of these cannabimimetic indoles, strongly suggest that these cannabinoid receptor ligands bind primarily by aromatic stacking interactions in the transmembrane helix 3-4-5-6 region of the CB1 receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.
• COMPOSITION AND METHODS TO IMPROVE STABILITY, DOSING, PHARMACODYNAMICS AND PRODUCT SHELF LIFE OF ENDOCANNABINOIDS, PHYTOCANNABINOIDS AND SYNTHETIC CANNABINOIDS DELIVERED BY NASAL INHALER
  申请人：Willinsky, Michael

  公开号：EP3247402A1

  公开（公告）日：2017-11-29
• ASSAY FOR CANNABINOIDS AND METHODS OF USE THEREOF
  申请人：Microgenics Corporation

  公开号：US20160025753A1

  公开（公告）日：2016-01-28

  Immunoassays, methods, and kits for qualitative and/or quantitative detection of cannabinoids in specimens including, without limitation, bodily fluids (e.g., blood, urine, oral fluid or sweat) or other biological specimens and potential drug samples.
• [EN] ASSAY FOR CANNABINOIDS AND METHODS OF USE THEREOF<br/>[FR] DOSAGE DE CANNABINOÏDES ET PROCÉDÉS D'UTILISATION DE CELUI-CI
  申请人：MICROGENICS CORP

  公开号：WO2016014773A1

  公开（公告）日：2016-01-28

  Immunoassays, methods, and kits for qualitative and/or quantitative detection of cannabinoids in specimens including, without limitation, bodily fluids (e.g., blood, urine, oral fluid or sweat) or other biological specimens and potential drug samples.