2-(cyclohex-1-en-1-yl)-1H-indole | 78329-40-5

• 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
• 英文名称: 2-(cyclohex-1-en-1-yl)-1H-indole
• 英文别名: 1H-Indole, 2-(1-cyclohexen-1-yl)-；2-(cyclohexen-1-yl)-1H-indole
• CAS: 78329-40-5
• 化学式: C₁₄H₁₅N
• 分子量: 197.28
• InChiKey: KJKXOZREZXQOQE-UHFFFAOYSA-N

物化性质

• 熔点：
  137-139 °C
• 沸点：
  373.3±21.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(cyclohex-1-en-1-yl)-1H-indole 在 palladium on activated charcoal 1-己烯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 benzo[a]pyrrolo[3,4-c]carbazole-1,3(2H,8H)-dione
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel poly(ADP-ribose) polymerase-1 inhibitors

  摘要：

  A series of novel pyrrolocarbazoles was synthesized as potential PARP-1 inhibitors. Pyrrolocarbazole 1 was identified as a potent PARP-I inhibitor (IC50 = 36 nM) from our internal database. Synthesis of analogs around this template with the aid of modeling studies led to the identification of the truncated imide 14. Compound 14 (IC50 = 40 nM), with deleted B-ring, was found to be an equipotent PARP-1 inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.099
• 作为产物：
  描述：

  1-(1H-吲哚-2-基)环己烷-1-醇 在 盐酸 作用下， 生成 2-(cyclohex-1-en-1-yl)-1H-indole
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel poly(ADP-ribose) polymerase-1 inhibitors

  摘要：

  A series of novel pyrrolocarbazoles was synthesized as potential PARP-1 inhibitors. Pyrrolocarbazole 1 was identified as a potent PARP-I inhibitor (IC50 = 36 nM) from our internal database. Synthesis of analogs around this template with the aid of modeling studies led to the identification of the truncated imide 14. Compound 14 (IC50 = 40 nM), with deleted B-ring, was found to be an equipotent PARP-1 inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.099

文献信息

• [EN] VIRAL POLYMERASE INHIBITORS<br/>[FR] INHIBITEURS DE POLYMERASE VIRALE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2004065367A1

  公开（公告）日：2004-08-05

  An isomer, enantiomer, diastereoisomer or tautomer of a compound, represented by formula (I): wherein wherein A, B, R2, R3, L, M1, M2, M3, M4, Y1, Y0, Z and Sp are as defined in claim 1, or a salt thereof, as an inhibitor of HCV NS5B polymerase.

  化合物的异构体、对映体、非对映异构体或互变异构体，由式(I)所代表：其中A、B、R2、R3、L、M1、M2、M3、M4、Y1、Y0、Z和Sp如权利要求1中定义，或其盐，作为HCV NS5B聚合酶的抑制剂。
• Photochemistry of Benzotriazoles: Generation of 1,3-Diradicals and Intermolecular Cycloaddition as a New Route toward Indoles and Dihydropyrrolo[3,4-b]Indoles
  作者：Nader Al-Jalal、Maher Ibrahim、Nouria Al-Awadi、Mohamed Elnagdi、Yehia Ibrahim

  DOI：10.3390/molecules191220695

  日期：——

  Irradiation of benzotriazoles 1a–e at λ = 254 nm in acetonitrile solution generated the corresponding 1,3-diradicals which underwent intermolecular cycloaddition with maleimides to afford the corresponding dihydropyrrolo[3,4-b]indoles and with acetylene derivatives to afford indoles as the major products. This offers an interesting and simple access to such ring systems of potential synthetic and biological

  在乙腈溶液中以 λ = 254 nm 照射苯并三唑 1a-e 产生相应的 1,3-双自由基，它们与马来酰亚胺进行分子间环加成反应，得到相应的二氢吡咯并 [3,4-b] 吲哚，并用乙炔衍生物得到吲哚作为主要产品。这提供了对具有潜在合成和生物学意义的此类环系统的有趣且简单的访问。光产物的结构是通过光谱和单晶 X 射线晶体学确定的。
• DBSA‐Catalyzed Regioselective Dehydrative Friedel‐Crafts Arylation of CF ₃ ‐Containing 3‐Indolyl(2‐thiophenyl)methanols with 2‐Substituted Indoles in Water
  作者：Di An、Xinzhu Miao、Xiangxiang Ling、Xianxiao Chen、Weidong Rao

  DOI：10.1002/adsc.202000020

  日期：2020.4.8

  A green and efficient regioselective dehydrative Friedel‐Crafts arylation of trifluorinated 3‐indolyl(2‐thiophenyl) methanols with 2‐substituted indoles, catalyzed by DBSA (dodecylbenzenesulfonic acid) in water is described. This simple and atom‐economical protocol features a unique regioselective 1,8‐addition, operational simplicity, mild conditions, excellent functional group compatibility, and environmental

  描述了由DBSA（十二烷基苯磺酸）在水中催化的绿色高效的区域选择性脱水Friedel-Crafts三氟3-吲哚基（2-噻吩基）甲醇与2-取代吲哚的芳基化反应。这种简单而经济的方案具有独特的区域选择性1,8-加成，操作简便，条件温和，出色的官能团相容性和环境友好性。
• Simple Indole Synthesis by One-Pot Sonogashira Coupling-NaOH-Mediated Cyclization
  作者：Roberto Sanz、Verónica Guilarte、M. Castroviejo

  DOI：10.1055/s-0028-1083624

  日期：2008.12

  Coupling of o-iodoanilines with terminal alkynes under standard Sonogashira conditions, and further treatment with NaOH under conventional heating or microwave irradiation, afford 2-substituted indoles in usually high yields. Functionalities such as halides, nitro, and cyano groups are tolerated under the reaction conditions.

  在标准Sonogashira条件下，将o-碘苯胺与末端炔烃偶联，并在常规加热或微波辐照下进一步处理NaOH，通常可以获得高产率的2-取代吲哚。在反应条件下，卤素、硝基和氰基等功能团均可耐受。
• CH Alkenylations with Alkenyl Acetates, Phosphates, Carbonates, and Carbamates by Cobalt Catalysis at 23 °C
  作者：Marc Moselage、Nicolas Sauermann、Sven C. Richter、Lutz Ackermann

  DOI：10.1002/anie.201412319

  日期：2015.5.18

  N‐heterocyclic carbene ligands enable direct arene alkenylations with easily accessible alkenyl acetates through regioselective CH/CO functionalizations in a stereoconvergent fashion. The versatile cobalt catalyst was broadly applicable and thus also allowed for the efficient conversion of alkenyl phosphates, carbonates, and carbamates at ambient temperature.

  便宜的钴催化剂与N-杂环碳烯配体能够通过区域选择性下用容易获得的烯基乙酸酯直接芳烃alkenylations  H / C  Ò官能化以stereoconvergent方式。通用的钴催化剂具有广泛的用途，因此也可以在环境温度下有效地转化烯基磷酸盐，碳酸盐和氨基甲酸酯。