3-[1-(2,2-Dimethylpropanoyl)indol-3-yl]propanoyl chloride | 1028267-60-8

• 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-[1-(2,2-Dimethylpropanoyl)indol-3-yl]propanoyl chloride
• CAS: 1028267-60-8
• 化学式: C₁₆H₁₈ClNO₂
• 分子量: 291.777
• InChiKey: QCKQVVKEEAQCPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  408.3±28.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 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：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[1-(2,2-Dimethylpropanoyl)indol-3-yl]propanoyl chloride 在 aluminum (III) chloride 、 氯化亚砜 、 盐酸羟胺 、 水 、 sodium acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 氯乙酰氯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 34.0h， 生成 3,4,5,6-tetrahydro-1H-azepino<5,4,3-cd>indol-6-one
  参考文献：
  名称：

  Poly(ADP-ribose) Polymerase in Neurodegeneration: Radiosynthesis and Radioligand Binding in ARC-SWE tg Mice

  摘要：

  We report the synthesis, radiosynthesis, and characterization of a radioligand for poly(ADP-ribose) polymerase (PARP). PARP is of central importance in cell homeostasis, neuroplasticity, and neurodegeneration in the brain. A radiolabeled PARP inhibitor was developed and used for autoradiographic quantification of PARP protein concentration in wild-type and transgenic rodent brains ex vivo in high resolution. The binding of [H-3]rucaparib was found to be confined to PARP-expressing domains, for example, cerebellar cortex or hippocampal regions in both models. Saturation binding experiments confirmed selective and reversible binding to a single site (K-d = 1.1 +/- 0.2 nM).

  DOI：

  10.1021/acschemneuro.8b00053
• 作为产物：
  描述：

  3-吲哚丙酸 在 正丁基锂 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 3-[1-(2,2-Dimethylpropanoyl)indol-3-yl]propanoyl chloride
  参考文献：
  名称：

  通过吲哚-3-基丙酰氯的区域选择性friedel-crafts环化反应，轻松实现拟酮的仿生合成

  摘要：

  在存在大量由氯乙酰氯和氯化铝产生的羰基碳氧离子的情况下，3-（1-三甲基乙酰吲哚-3基）-丙酰氯区域选择性地反应，以极好的收率得到Uhle酮的新戊酰衍生物。

  DOI：

  10.1016/0040-4039(94)88275-4

文献信息

• Concise and very efficient synthesis of the N-methylwelwistatin tetracyclic core based on an anionic domino process
  作者：Miriam Ruiz、Pilar López-Alvarado、J. Carlos Menéndez

  DOI：10.1039/c0ob00382d

  日期：——

  An efficient synthesis of the N-methylwelwistatin tetracyclic core in only two steps from Kornfeld's ketone is described, whose key transformation involves the generation of a fused bicyclo[4.3.1]decane ring system through a one-pot sequence comprising a Michael-intramolecular aldolization anionic domino process and a DBU-promoted hydrolysis of the N-pivaloyl protecting group. Besides providing the

  描述了仅需两步即可从Kornfeld's酮高效合成N-甲基welwistatin四环核的方法，其关键转变包括通过一个包含迈克尔-分子内醛缩醛化反应的一锅序列生成稠合的双环[4.3.1]癸烷环系统。阴离子多米诺过程和DBU促进的N-新戊酰基保护基水解。除了提供迄今为止最有效的威维他汀核心的合成方法外，该方法还具有在威维他汀D环上安装氧化功能的优势。
• Conformationally constrained amino-acids: Synthesis of novel β, β-, 2,3-, and 3,4-cyclised tryptophans
  作者：David C. Horwell、Mary J. McKiernan、Simon Osborne

  DOI：10.1016/s0040-4039(98)01920-0

  日期：1998.11

  The synthesis of novel conformationally constrained tryptophan mimetics is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
• [EN] ERGOLINE-DERIVED AGONISTS OF THE 5-HT2A RECEPTOR<br/>[FR] AGONISTES DÉRIVÉS D'ERGOLINE DU RÉCEPTEUR 5-HT2A
  申请人：[en]DIAMOND THERAPEUTICS INC.

  公开号：WO2023073423A1

  公开（公告）日：2023-05-04

  Provided herein are novel lisuride compounds, processes for their preparation, compositions comprising said compounds, and use in therapy. More particularly, the present disclosure relates to fluorinated and/or deuterated analog useful in the treatment of diseases, disorders or conditions treatable by modulating ther 5-HT2 receptor subtypes.
• A facile biomimetic synthesis of uhle's ketone by the regioselective friedel-crafts cyclization of indole-3-ylpropionyl chloride
  作者：Katsunori Teranishi、Syunzi Hayashi、Shin-ichi Nakatsuka、Toshio Goto

  DOI：10.1016/0040-4039(94)88275-4

  日期：1994.10

  In the presence of a larg amount of oxocarbonium ion species generated from chloroacetyl chloride and aluminum chloride, 3-(1-trimethylacetylindol-3yl)-propionyl chloride reacts regioselectively to give a pivaloyl derivative of Uhle's ketone in excellent yield.

  在存在大量由氯乙酰氯和氯化铝产生的羰基碳氧离子的情况下，3-（1-三甲基乙酰吲哚-3基）-丙酰氯区域选择性地反应，以极好的收率得到Uhle酮的新戊酰衍生物。
• Poly(ADP-ribose) Polymerase in Neurodegeneration: Radiosynthesis and Radioligand Binding in ARC-SWE tg Mice
  作者：Santosh R. Alluri、Patrick J. Riss

  DOI：10.1021/acschemneuro.8b00053

  日期：2018.6.20

  We report the synthesis, radiosynthesis, and characterization of a radioligand for poly(ADP-ribose) polymerase (PARP). PARP is of central importance in cell homeostasis, neuroplasticity, and neurodegeneration in the brain. A radiolabeled PARP inhibitor was developed and used for autoradiographic quantification of PARP protein concentration in wild-type and transgenic rodent brains ex vivo in high resolution. The binding of [H-3]rucaparib was found to be confined to PARP-expressing domains, for example, cerebellar cortex or hippocampal regions in both models. Saturation binding experiments confirmed selective and reversible binding to a single site (K-d = 1.1 +/- 0.2 nM).