3-(5-chloro-1H-indol-3-yl)propanal | 843656-18-8

• 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: 3-(5-chloro-1H-indol-3-yl)propanal
• CAS: 843656-18-8
• 化学式: C₁₁H₁₀ClNO
• 分子量: 207.659
• InChiKey: WVJAOFXEMFUYEY-UHFFFAOYSA-N

物化性质

• 沸点：
  376.9±27.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(5-chloro-1H-indol-3-yl)propanal 在 C₁₆H₂₁N₃Rh⁽²⁺⁾*2F₆Sb^(1-) 、 cesium acetate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 74.75h， 生成
  参考文献：
  名称：

  含重氮化合物的铑催化的吲哚CH-H功能化：结构多样的2,3-熔融吲哚的合成

  摘要：

  据报道，铑通过重氮化合物催化吲哚的C2-H官能化，然后向C = O或C = C键分子内亲核加成，从而合成了2,3稠合的吲哚。除受体/受体重氮化合物外，对受体/受体重氮化合物的耐受性也很广，可为各种2,3稠合的吲哚提供完美的非对映控制。值得注意的是，通过简单地改变反应条件，在吲哚的C 2和C 7位置处的选择性CH 2-二烷基化反应也已经发展。这种对环境无害的转化会在温和的条件下进行，从而使二氮成为唯一的副产物。

  DOI：

  10.1002/adsc.201700974
• 作为产物：
  描述：

  3-(5-chloro-1H-indol-3-yl)propan-1-ol 在 吡啶 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 以 氯苯 为溶剂， 反应 16.0h， 以61%的产率得到3-(5-chloro-1H-indol-3-yl)propanal
  参考文献：
  名称：

  Advances toward New Antidepressants with Dual Serotonin Transporter and 5-HT_1A Receptor Affinity within a Class of 3-Aminochroman Derivatives. Part 2

  摘要：

  Novel compounds combining a 5-HT1A moiety (3-aminochroman scaffold) and a 5-HT transporter (indole analogues) linked through,a common basic nitrogen via an alkyl chain attached at the 1- or 3-position of the indole were evaluated for dual affinity at both the 5-HT reuptake site and the 5-HT1A receptor. Compounds of most interest were found to have a 5-carbamoyl-8-fluoro-3-amino-3,4-dihydro-2H-1-benzopyran linked to a 3-alkylindole (straight chain), more specifically substituted with a 5-fluoro ((R)-(-)-35c), 5-cyano ((-)-52a), or 5,7-difluoro ((-)-52g). Several factors contributed to 5-HT1A affinity, serotonin rat transporter affinity, and functional antagonism in vitro. Although most of our analogues showed good to excellent affinities at both targets, specific features such as cyclobutyl substitution on the basic nitrogen and stereochemistry at the 3-position of the chroman moiety seemed necessary for antagonism at the 5-HT1A receptor. Branched linkers seemed to impart antagonism even as racemates, however, potency of these analogues in the functional assay was not desirable enough to further pursue these compounds.

  DOI：

  10.1021/jm8007097

文献信息

• Conjugate Addition of Electron-rich Aromatics to Acrolein in the Confined Space of Zeolite Y
  作者：Shouhei Imachi、Makoto Onaka

  DOI：10.1246/cl.2005.708

  日期：2005.5

  Acrolein gas was spontaneously entrapped in supercages of NaY zeolite and the sorption was confirmed by solid 13C MAS NMR spectra. In the confined cavities, acrolein smoothly underwent conjugate addition with electron-rich aromatics such as indoles and anisole.

  丙烯醛气体自发地被捕获在NaY沸石的超级笼中，通过固态13C魔角旋转核磁共振（MAS NMR）谱确认了吸附现象。在受限的孔道中，丙烯醛能够顺利地与富电子芳香化合物如吲哚和茴香醚发生亲核加成反应。
• Palladium-Mediated Oxidative Annulation of δ-Indolyl-α,β-Unsaturated Compounds toward the Synthesis of Cyclopenta[<i>b</i>]indoles and Heterogeneous Hydrogenation To Access Fused Indolines
  作者：André Capretz Agy、Manoel T. Rodrigues、Lucas A. Zeoly、Deborah A. Simoni、Fernando Coelho

  DOI：10.1021/acs.joc.9b00505

  日期：2019.5.3

  The cyclopenta[b]indole moiety represents a key skeletal unit in several natural and synthetic compounds that exhibit diverse biological properties. We described herein a two-step sequence for synthesizing cyclopenta[b]indoles with great structural diversity in overall yields up to 37%. The key step was a palladium-catalyzed oxidative annulation of 3-alkylindoles (Fujiwara–Moritani reaction). The obtained

  环戊[ b ]吲哚部分代表几种天然和合成化合物的关键骨架单元，这些化合物表现出多种生物学特性。我们在本文中描述了用于合成具有巨大结构多样性的环戊并[ b ]吲哚的两步序列，总产率高达37％。关键步骤是钯催化的3-烷基吲哚的氧化环化反应（藤原-莫里塔尼反应）。所获得的环戊[ b ]吲哚被用作非均相氢化反应的底物，从而以中等收率提供了新的熔融二氢吲哚。三个这样的二氢吲哚的酸催化的分子内环化反应以89％，90％和61％的收率得到四环内酰胺。
• [EN] 3-AMINO CHOMAN AND 2-AMINO TETRALIN DERIVATIVES<br/>[FR] DERIVES 3-AMINO CHOMANE ET 2-AMINO TETRALINE
  申请人：WYETH CORP

  公开号：WO2005012291A1

  公开（公告）日：2005-02-10

  3-Amino chroman and 2-amino tetralin derivatives and compositions containing such compounds are disclosed. Methods of using the 3-amino chroman and 2-amino tetralin compounds and compositions containing such compounds in the treatment of serotonin disorders, such as depression and anxiety, are also disclosed.

  揭示了3-氨基色苷和2-氨基四氢萘衍生物以及含有这些化合物的组合物。还揭示了在治疗血清素失调症，如抑郁症和焦虑症中使用3-氨基色苷和2-氨基四氢萘化合物以及含有这些化合物的组合物的方法。
• 3-Amino chroman and 2-amino tetralin derivatives
  申请人：Hatzenbuhler Theriault Nicole

  公开号：US20050032873A1

  公开（公告）日：2005-02-10

  3-Amino chroman and 2-amino tetralin derivatives and compositions containing such compounds are disclosed. Methods of using the 3-amino chroman and 2-amino tetralin compounds and compositions containing such compounds in the treatment of serotonin disorders, such as depression and anxiety, are also disclosed.

  本文披露了3-氨基色满和2-氨基四氢萘衍生物及含有这些化合物的组合物。还披露了使用3-氨基色满和2-氨基四氢萘化合物及含有这些化合物的组合物治疗血清素失调症，如抑郁和焦虑的方法。
• Bi-functional complexes and methods for making and using such complexes
  申请人：Gouliaev Alex Haahr

  公开号：US11225655B2

  公开（公告）日：2022-01-18

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.

  本发明涉及一种合成双功能复合物的方法，该复合物包括分子部分和识别分子部分的识别寡核苷酸部分。根据本发明的合成方法的一部分优选在一种或多种有机溶剂中进行，此时包含可选保护标签或寡核苷酸标识符的新生双功能复合物与固体支持物相连接，合成方法的另一部分优选在适合于将寡核苷酸标签酶加到溶液中的新生双功能复合物的条件下进行。