morpholino(1H-pyrrol-2-yl)methanone | 851384-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: morpholino(1H-pyrrol-2-yl)methanone
• 英文别名: 4-Morpholinyl-1H-pyrrol-2-ylmethanone；morpholin-4-yl(1H-pyrrol-2-yl)methanone
• CAS: 851384-79-7
• 化学式: C₉H₁₂N₂O₂
• mdl: MFCD21101516
• 分子量: 180.206
• InChiKey: FSFYYGOUHDPGGA-UHFFFAOYSA-N

物化性质

• 沸点：
  391.6±32.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  morpholino(1H-pyrrol-2-yl)methanone 在 碘 、 叔丁基锂 、 silver trifluoroacetate 作用下， 以 四氢呋喃 、 氯仿 、 正戊烷 为溶剂， 反应 22.5h， 生成 6,7-dimethoxy-5H-pyrrolo[1,2-b]isoquinolin-10-one
  参考文献：
  名称：

  An efficient entry to pyrrolo[1,2-b]isoquinolines and related systems through Parham cyclisation

  摘要：

  Aryllithiums generated by lithium-iodine exchange undergo intramolecular cyclisation to give pyrrolo[1,2-b]isoquinolines, in high yields. The best results were obtained when Weinreb or morpholine amides were used as internal electrophiles. The procedure has been extended to the preparation of seven and eight membered rings, opening a route to benzazepine and benzazocine skeletons. (c) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.105
• 作为产物：
  描述：

  (1H-吡咯-2-基)-甲醇 、 吗啡啉盐酸盐 在 叔丁基过氧化氢 、 tris(bipyridine)ruthenium(II) dichloride hexahydrate 、 calcium carbonate 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 72.0h， 以74%的产率得到morpholino(1H-pyrrol-2-yl)methanone
  参考文献：
  名称：

  可见光光氧化还原催化的苄醇酰胺化反应。

  摘要：

  提出了一种新的光催化途径，该途径是由可见光介导的由醇和胺转化为酰胺的。该反应在作为溶剂的乙酸乙酯中进行。乙酸乙酯可以定义为绿色和生物基溶剂。诸如能源之类的原材料容易获得，稳定且便宜。该反应显示出一般性和高产率。

  DOI：

  10.1021/acs.joc.0c01320

文献信息

• 신규한 메타논 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 망막 질환의 예방 또는 치료용 약학적 조성물
  申请人：The Industry & Academic Cooperation in Chungnam National University (IAC) 충남대학교산학협력단(220040084104) BRN ▼314-82-09264

  公开号：KR101555033B1

  公开（公告）日：2015-09-23

  본 발명은 신규한 메타논 유도체, 이의 제조방법, 및 이를 유효성분으로 함유하는 망막 질환의 예방 또는 치료용 약학적 조성물에 관한 것으로, 본 발명에 따른 신규한 메타논 유도체, 이의 광학 이성질체, 또는 이의 약학적으로 허용가능한 염은 RIPK1(Receptor-interacting serine/threonine-protein kinase 1)의 억제 효과가 뛰어나므로, 이를 유효성분으로 함유하는 조성물은 색소성 망막염 (RP), 레베르 선천 흑암시 (LCA), 스타가르트병, 어셔 증후군, 맥락막 결여, 로드-콘 또는 콘-로드 디스트로피, 섬모병증, 미토콘드리아 장애, 진행성 망막 위축증, 퇴행성 망막 질환, 노화-관련된 황반 변성 (AMD), 습성 AMD, 건성 AMD, 지도상 위축증, 가족형 또는 획득 황반병증, 망막 광수용체 질환, 망막 색소 상피-계 질환, 당뇨병성 망막증, 낭포성 황반 부종, 포도막염, 망막박리, 외상성 망막 손상, 의원성 망막 손상, 황반 원공, 황반 모세관확장증, 신경절 세포 질환, 시신경 세포 질환, 녹내장, 시신경병증, 허혈성 망막 질환, 미숙아 망막증, 망막 혈관 폐색, 가족형 마크로아뉴리즘, 망막 혈관 질환, 안혈관 질환, 녹내장으로 인한 망막신경세포 퇴화, 또는 허혈성 시신경병증 등의 망막 질환의 예방 또는 치료용 약학적 조성물로 유용하게 사용될 수 있다.

  本发明涉及一种新型的甲酮衍生物，其制备方法，以及用作视网膜疾病的预防或治疗药物组合物，根据本发明，由于新型的甲酮衍生物，其光学异构体或药学上可接受的盐具有出色的RIPK1（受体相互作用丝氨酸/苏氨酸蛋白激酶1）抑制作用，因此包含其作为有效成分的组合物可用作色素性视网膜炎（RP），勒贝尔先天性黑暗症（LCA），斯塔加特病，阿什尔综合征，脉络膜缺陷，罗德-锥或锥-罗德萎缩症，圆锥细胞病，线粒体疾病，进行性视网膜萎缩症，变性性视网膜疾病，与衰老相关的黄斑变性（AMD），湿性AMD，干性AMD，地图样萎缩症，家族性或获得性黄斑病变，视网膜光感受器疾病，视网膜色素上皮相关疾病，糖尿病性视网膜病变，囊性黄斑水肿，葡萄膜炎，视网膜脱离，创伤性视网膜损伤，原发性视网膜损伤，黄斑囊肿，黄斑脉络膨胀症，神经节细胞疾病，视神经细胞疾病，青光眼，视神经病变，缺血性视网膜疾病，未成熟婴儿视网膜病变，视网膜血管闭塞，家族性巨动脉瘤，视网膜血管疾病，眼内血管疾病，由青光眼引起的视神经细胞退化，或缺血性视神经病变等视网膜疾病的预防或治疗药物组合物可被有效地使用。
• Divergent synthesis of pyrrole carboxamides from pyrrole carboxaldehyde and formamides/amines <i>via</i> oxidative amidation involving pyrrole acyl radicals
  作者：Joydev K. Laha、Surabhi Panday、J. Patrick Weber、Martin Breugst

  DOI：10.1039/d3cc02766j

  日期：——

  A non-traditional approach for the synthesis of pyrrole carboxamides from pyrrole carboxaldehyde and formamides or amines with catalytic amounts of nBu4NI and TBHP as oxidants is reported herein. The method is operationally simple providing straightforward access to primary, secondary, and tertiary pyrrole carboxamides in good to excellent yields utilizing inexpensive reagents under mild conditions

  本文报道了一种由吡咯甲醛和甲酰胺或胺以催化量的n Bu 4 NI和TBHP作为氧化剂合成吡咯甲酰胺的非传统方法。该方法操作简单，可在温和条件下利用廉价试剂以良好至优异的产率直接获得伯、仲和叔吡咯甲酰胺。与涉及离子反应的传统酰胺化不同，我们当前方法的机理研究揭示了 2- 或 3-吡咯酰基自由基的参与，否则很少假设。本方法的适用性在类药物化合物，即光学纯的碳依托咪酯酰胺的合成中得到进一步证明。
• Intramolecular cyclisation of functionalised heteroaryllithiums. Synthesis of novel indolizinone-based compounds
  作者：Javier Ruiz、Esther Lete、Nuria Sotomayor

  DOI：10.1016/j.tet.2006.04.057

  日期：2006.6

  The intramolecular cyclisation of heteroaryllithiums derived from N-heteroarylmethylpyrrole-2-carboxam ides takes place smoothly at low temperature when N-methoxy-N-methyl and morpholine amides are used as internal electrophiles. Halogen-lithium exchange using n-BuLi is the method of choice to achieve metalation on the quinoline and pyridine derivatives, while directed lithiation (LDA) works better for furan. In the case of thiophene both methodologies can be applied. These metalation-cyclisation sequences provide a useful entry to several types of indolizidine based compounds (pyrrolo[1,2-b]acridinones, pyrrolo[1,2-g]quinolones, thieno and furo[3,2-f]indolizinones). (c) 2006 Elsevier Ltd. All rights reserved.
• Visible-Light Photoredox-Catalyzed Amidation of Benzylic Alcohols
  作者：Silvia Gaspa、Andrea Farina、Mariella Tilocca、Andrea Porcheddu、Luisa Pisano、Massimo Carraro、Ugo Azzena、Lidia De Luca

  DOI：10.1021/acs.joc.0c01320

  日期：2020.9.18

  A new photocatalyzed route to amides from alcohols and amines mediated by visible light is presented. The reaction is carried out in ethyl acetate as a solvent. Ethyl acetate can be defined a green and bio-based solvent. The starting materials such as the energy source are easily available, stable, and inexpensive. The reaction has shown to be general and high yielding.

  提出了一种新的光催化途径，该途径是由可见光介导的由醇和胺转化为酰胺的。该反应在作为溶剂的乙酸乙酯中进行。乙酸乙酯可以定义为绿色和生物基溶剂。诸如能源之类的原材料容易获得，稳定且便宜。该反应显示出一般性和高产率。
• An efficient entry to pyrrolo[1,2-b]isoquinolines and related systems through Parham cyclisation
  作者：Javier Ruiz、Ainhoa Ardeo、Roberto Ignacio、Nuria Sotomayor、Esther Lete

  DOI：10.1016/j.tet.2004.10.105

  日期：2005.3

  Aryllithiums generated by lithium-iodine exchange undergo intramolecular cyclisation to give pyrrolo[1,2-b]isoquinolines, in high yields. The best results were obtained when Weinreb or morpholine amides were used as internal electrophiles. The procedure has been extended to the preparation of seven and eight membered rings, opening a route to benzazepine and benzazocine skeletons. (c) 2004 Elsevier Ltd. All rights reserved.