6-methoxy-3,4-dihydroquinoline-1(2H)-carbonyl chloride | 1424284-39-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-methoxy-3,4-dihydroquinoline-1(2H)-carbonyl chloride
• 英文别名: 3,4-Dihydro-6-methoxy-1(2h)-quinolinecarbonyl chloride；6-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl chloride
• CAS: 1424284-39-8
• 化学式: C₁₁H₁₂ClNO₂
• 分子量: 225.675
• InChiKey: NNFINISVZGOCIX-UHFFFAOYSA-N

物化性质

• 沸点：
  408.8±44.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methoxy-3,4-dihydroquinoline-1(2H)-carbonyl chloride 在 正丁基锂 、 碘 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 26.0h， 生成 2-iodo-1-(thiophen-3-yl)-6,7-dihydro-3H-pyrrolo[2,1-j]quinoline-3,9(5H)-dione
  参考文献：
  名称：

  Synthesis of pyrrolo-[2,1-j]quinolone framework via intramolecular electrophilic ipso-cyclization

  摘要：

  The challenging pyrrolo-12,1-j]quinolone core structure has been synthesized from N-(alkynoyl)-6-methoxytetrahydroquinoline in good yields using electrophilic cyclization as the key step. These reactions require simple starting materials and mild reaction conditions. In addition, we have demonstrated that the iodine moiety, which could be easily introduced in the final step, is very useful for further functionalization by employing various palladium-catalyzed cross-coupling reactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.014
• 作为产物：
  描述：

  光气 、 6-甲氧基-1,2,3,4-四氢喹啉 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 以80%的产率得到6-methoxy-3,4-dihydroquinoline-1(2H)-carbonyl chloride
  参考文献：
  名称：

  Synthesis of pyrrolo-[2,1-j]quinolone framework via intramolecular electrophilic ipso-cyclization

  摘要：

  The challenging pyrrolo-12,1-j]quinolone core structure has been synthesized from N-(alkynoyl)-6-methoxytetrahydroquinoline in good yields using electrophilic cyclization as the key step. These reactions require simple starting materials and mild reaction conditions. In addition, we have demonstrated that the iodine moiety, which could be easily introduced in the final step, is very useful for further functionalization by employing various palladium-catalyzed cross-coupling reactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.014

文献信息

• Medium-Ring Nitrogen Heterocycles through Migratory Ring Expansion of Metalated Ureas
  作者：Jessica E. Hall、Johnathan V. Matlock、John W. Ward、Katharine V. Gray、Jonathan Clayden

  DOI：10.1002/anie.201605714

  日期：2016.9.5

  benzo‐fused nitrogen heterocycles (indolines, tetrahydroquinolines, and their homologues) undergo migratory ring expansion through deprotonation of their benzylic urea derivatives with lithium diisopropylamide (LDA) in the presence of N,N′‐dimethylpropylideneurea (DMPU). The products of the reactions are benzodiazepines, benzodiazocines, and their homologues, with ring sizes of 8–12. The reactions tolerate a

  简单的苯并稠合的氮杂环（二氢吲哚，四氢喹啉及其同系物）在N，N'-二甲基丙稀酰胺（DMPU）的存在下，通过其苄基脲衍生物与二异丙基氨基化锂（LDA）的去质子化而经历迁移环扩展。反应的产物是苯并二氮杂,、苯并二氮杂s及其同系物，环大小为8-12。该反应容许一定范围的取代基图案和类型，并且可以表现出对映特异性或非对映选择性。这些难以获得的中环氮杂环的有效合成迅速产生了相当大的复杂性。
• In vivo engineered cereblon protein
  申请人：Vividion Therapeutics, Inc.

  公开号：US10781239B2

  公开（公告）日：2020-09-22

  Disclosed herein are in vivo engineered cereblon protein and methods of making the same. The in vivo engineered cereblon protein can include a site-specific non-naturally occurring modification at cysteine 287 as set forth in SEQ ID NO:1, or cysteine 286 as set forth in SEQ ID NO:2 or 3, the modification comprising a moiety resulting from an in vivo Michael addition reaction between an exogenous Michael acceptor and the cysteine 287 as set forth in SEQ ID NO:1, or cysteine 286 as set forth in SEQ ID NO:2 or 3.

  本文公开了体内工程化脑龙蛋白及其制造方法。体内工程化脑龙蛋白可包括 SEQ ID NO:1 所列半胱氨酸 287 或 SEQ ID NO:2 或 3 所列半胱氨酸 286 的位点特异性非天然发生修饰，该修饰包括外源迈克尔受体与 SEQ ID NO:1 所列半胱氨酸 287 或 SEQ ID NO:2 或 3 所列半胱氨酸 286 之间的体内迈克尔加成反应产生的分子。
• IN VIVO ENGINEERED CEREBLON PROTEIN
  申请人：Vividion Therapeutics, Inc.

  公开号：US20200216507A1

  公开（公告）日：2020-07-09

  Disclosed herein are in vivo engineered cereblon protein and methods of making the same. The in vivo engineered cereblon protein can include a site-specific non-naturally occurring modification at cysteine 287 as set forth in SEQ ID NO:1, or cysteine 286 as set forth in SEQ ID NO: 2 or 3, the modification comprising a moiety resulting from an in vivo Michael addition reaction between an exogenous Michael acceptor and the cysteine 287 as set forth in SEQ ID NO:1, or cysteine 286 as set forth in SEQ ID NO: 2 or 3.