5-碘苯酞 | 41284-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 中文名称: 5-碘苯酞
• 英文名称: 5-iodoisobenzofuran-1(3H)-one
• 英文别名: 5-iodo-phthalide；5-Jod-phthalid；5-iodo-3H-isobenzofuran-1-one；5-iodo-2-benzofuran-1(3H)-one；5-Iodophthalide；5-iodo-3H-2-benzofuran-1-one
• CAS: 41284-92-8
• 化学式: C₈H₅IO₂
• 分子量: 260.031
• InChiKey: CQAKANQMFXBJJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  193 °C
• 沸点：
  397.4±42.0 °C(Predicted)
• 密度：
  2.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-碘苯酞 在 bis-triphenylphosphine-palladium(II) chloride 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium fluoride 、 sodium carbonate 、 silver nitrate 作用下， 以 乙醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 3.0h， 生成 5-(5-(2-methoxyphenyl)thiophen-2-yl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  Diarylthiophenes as inhibitors of the pore-forming protein perforin

  摘要：

  Evolution from a furan-containing high-throughput screen (HTS) hit (1) resulted in isobenzofuran-1(3H)-one (2) as a potent inhibitor of the function of both isolated perforin protein and perforin delivered in situ by intact KHYG-1 NK cells. In the current study, structure-activity relationship (SAR) development towards a novel series of diarylthiophene analogues has continued through the use of substituted-benzene and -pyridyl moieties as bioisosteres for 2-thioxoimidazolidin-4-one (A) on a thiophene (B) -isobenzofuranone (C) scaffold. The resulting compounds were tested for their ability to inhibit perforin lytic activity in vitro. Carboxamide (23) shows a 4-fold increase over (2) in lytic activity against isolated perforin and provides good rationale for continued development within this class. (C) 2015 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license.

  DOI：

  10.1016/j.bmcl.2015.12.003
• 作为产物：
  描述：

  5-溴苯酞 在 copper(l) iodide 、 (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 、 sodium iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以87%的产率得到5-碘苯酞
  参考文献：
  名称：

  Diarylthiophenes as inhibitors of the pore-forming protein perforin

  摘要：

  Evolution from a furan-containing high-throughput screen (HTS) hit (1) resulted in isobenzofuran-1(3H)-one (2) as a potent inhibitor of the function of both isolated perforin protein and perforin delivered in situ by intact KHYG-1 NK cells. In the current study, structure-activity relationship (SAR) development towards a novel series of diarylthiophene analogues has continued through the use of substituted-benzene and -pyridyl moieties as bioisosteres for 2-thioxoimidazolidin-4-one (A) on a thiophene (B) -isobenzofuranone (C) scaffold. The resulting compounds were tested for their ability to inhibit perforin lytic activity in vitro. Carboxamide (23) shows a 4-fold increase over (2) in lytic activity against isolated perforin and provides good rationale for continued development within this class. (C) 2015 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license.

  DOI：

  10.1016/j.bmcl.2015.12.003

文献信息

• <i>gem</i> ‐Difluoroallylation of Aryl Halides and Pseudo Halides with Difluoroallylboron Reagents in High Regioselectivity
  作者：Shu Sakamoto、Trevor W. Butcher、Jonathan L. Yang、John F. Hartwig

  DOI：10.1002/anie.202111476

  日期：2021.12

  coupling of a difluoroallylboronate with aryl and heteroaryl halides and triflates provides a convenient and broadly applicable synthesis of difluoroallylarenes. The difluoroallyl boron reagent is formed by a copper-catalyzed defluorinative borylation of the inexpensive reagent 3,3,3-trifluoropropene, and the products undergo a wide range of reactions to a series of difluoro-substituted analogs of common

  二氟烯丙基硼酸酯与芳基和杂芳基卤化物和三氟甲磺酸酯的偶联提供了方便且广泛适用的二氟烯丙基芳烃的合成。二氟烯丙基硼试剂是通过铜催化的廉价试剂 3,3,3-三氟丙烯的脱氟硼基化形成的，并且产物经历广泛的反应，形成一系列常见的具有生物价值的结构单元的二氟取代的类似物。
• Method for the preparation of citalopram
  申请人：H. Lundbeck A/S

  公开号：US20020077353A1

  公开（公告）日：2002-06-20

  Method for the preparation of citalopram comprising reaction of a compound of Formula (IV) 1 wherein R is halogen, or CF 3 —(CF 2 ) n —SO 2 —, n being 0 to 8, with a cyanide source in the presence of a palladium catalyst and a catalytic amount of C + or Zn 2+ , or with Zn(CN) 2 in the presence of a palladium catalyst.

  制备西酞普兰的方法包括在存在钯催化剂和催化量的C+或Zn2+的情况下，将化合物IV的反应物（其中R为卤素，或CF3—(CF2)n—SO2—，n为0至8）与氰化物源反应，或在存在钯催化剂的情况下将其与Zn(CN)2反应。
• Photoredox mediated C N cross coupling of sulfoximines with aryl iodides
  作者：Sudhir Hande、Adelphe Mfuh、Scott Throner、Ye Wu、Qing Ye、XiaoLan Zheng

  DOI：10.1016/j.tetlet.2019.151100

  日期：2019.10

  A new photoredox-catalyzed CN coupling reaction of sulfoximines with aryl halides has been developed for a general N-arylation of sulfoximines. The reactions proceed in the presence of visible light with high levels of chemoselectivity and a wide range of functionality is tolerated. There is a rapidly increasing interest in sulfoximines as pharmacophores in drug discovery and this new method offers

  已经开发了新的光氧化还原催化的亚砜亚砜与芳基卤化物的C N偶联反应，用于亚砜亚砜的一般N-芳基化。反应在具有高化学选择性水平的可见光存在下进行，并且宽泛的功能性是可以容忍的。在药物发现中，对亚砜亚砜作为药效团的兴趣迅速增长，这种新方法在高官能团耐受性和化合物的后期官能化方面提供了潜力。
• [EN] A PROCESS FOR THE PREPARATION OF ESCITALOPRAM<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE L'ESCITALOPRAM
  申请人：NATCO PHARMA LTD

  公开号：WO2006025071A1

  公开（公告）日：2006-03-09

  The present invention relates to an improved process for the preparation of escitalopram of the formula-(I) which consists of a sequential double Grignard reaction on 5-iodophthalide to get the dihydroxy compound of formula-(XVI), its resolution using a chiral acid, cyclization of resolved compound of the formula-(XVII), and cyanation of compound of the formula-(XVIII) using DMF and copper (I) cyanide. The present process utilizes the facile displacement of iodo group with cyano group in the final step of escitalopram. Escitalopram is a widely used anti-depressant.

  本发明涉及一种改进的制备埃司他普兰的方法，其包括在5-碘邻苯二甲酸酯上进行顺序双格氏试剂反应，得到化学式-(XVI)的二羟基化合物，使用手性酸对该化合物进行分离，环化分离后的化合物得到化学式-(XVII)，并使用DMF和铜(I)氰化物对化学式-(XVIII)的化合物进行氰化。本方法利用在埃司他普兰的最后一步中碘原子与氰基易于替换的特性。埃司他普兰是一种广泛使用的抗抑郁药物。
• METHOD FOR THE PREPARATION OF CITALOPRAM
  申请人：H. Lundbeck A/S

  公开号：US20020198391A1

  公开（公告）日：2002-12-26

  The invention provides a new and improved method for the preparation of 5-cyano-phtalid, which is a key intermediate in the preparation of the antidepressant compound citalopram.

  本发明提供了一种新的和改进的制备5-氰基邻酞酸的方法，该方法是制备抗抑郁化合物西酞普兰的关键中间体。