(2E)-3-{1-[(4-甲基苯基)磺酰基]-1H-吲哚-3-基}丙烯酸 | 164531-22-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2E)-3-{1-[(4-甲基苯基)磺酰基]-1H-吲哚-3-基}丙烯酸
• 英文名称: trans-β-<1-(p-Toluenesulfonyl)indol-3-yl>acrylic acid
• 英文别名: trans-β-<1-(p-tolylsulfonyl)indol-3-yl>acrylic acid；3-{1-[(4-Methylphenyl)sulfonyl]-1h-indol-3-yl}acrylic acid；(E)-3-[1-(4-methylphenyl)sulfonylindol-3-yl]prop-2-enoic acid
• CAS: 164531-22-0
• 化学式: C₁₈H₁₅NO₄S
• 分子量: 341.387
• InChiKey: XOIGITWGUHKORS-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E)-3-{1-[(4-甲基苯基)磺酰基]-1H-吲哚-3-基}丙烯酸 在 copper(l) iodide 溴 、 N,N-二甲基甘氨酸盐酸盐 、 caesium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (2R,3S)-N-[(Z)-2-[1-(4-methylphenyl)sulfonylindol-3-yl]ethenyl]-3-phenyloxirane-2-carboxamide
  参考文献：
  名称：

  Highly Efficient and Stereoselective N-Vinylation of Oxiranecarboxamides and Unprecedented 8-endo-Epoxy-arene Cyclization:  Expedient and Biomimetic Synthesis of Some Clausena Alkaloids

  摘要：

  Catalyzed by CuI/N,N-dimethylglycine, oxiranecarboxamides underwent a highly efficient and stereoselective N-vinylation reaction with (Z)-1-aryl-2-bromoethenes to afford the corresponding enamides. The method has been applied to a straightforward synthesis of (-)-(2R,3S)-SB204900, the enantiomer of the natural product. Following a hypothetic biomimetic pathway, both (+)-(5R,6S)-xi-Clausenamide and (-)-(5R,6S)-balasubramide have been efficiently synthesized for the first time through the unprecedented intramolecular 8-endo-epoxy-arene cyclization of (Z)-N-(phenylvinyl)oxiranecarboxamides.

  DOI：

  10.1021/ol070292+
• 作为产物：
  描述：

  3-吲哚甲醛 在 哌啶 、 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2E)-3-{1-[(4-甲基苯基)磺酰基]-1H-吲哚-3-基}丙烯酸
  参考文献：
  名称：

  Highly Efficient and Stereoselective N-Vinylation of Oxiranecarboxamides and Unprecedented 8-endo-Epoxy-arene Cyclization:  Expedient and Biomimetic Synthesis of Some Clausena Alkaloids

  摘要：

  Catalyzed by CuI/N,N-dimethylglycine, oxiranecarboxamides underwent a highly efficient and stereoselective N-vinylation reaction with (Z)-1-aryl-2-bromoethenes to afford the corresponding enamides. The method has been applied to a straightforward synthesis of (-)-(2R,3S)-SB204900, the enantiomer of the natural product. Following a hypothetic biomimetic pathway, both (+)-(5R,6S)-xi-Clausenamide and (-)-(5R,6S)-balasubramide have been efficiently synthesized for the first time through the unprecedented intramolecular 8-endo-epoxy-arene cyclization of (Z)-N-(phenylvinyl)oxiranecarboxamides.

  DOI：

  10.1021/ol070292+

文献信息

• Synthesis and Serotonin Receptor Affinities of a Series of <i>trans</i>-2-(Indol-3-yl)cyclopropylamine Derivatives
  作者：Suwanna Vangveravong、Arthi Kanthasamy、Virginia L. Lucaites、David L. Nelson、David E. Nichols

  DOI：10.1021/jm980318q

  日期：1998.12.1

  ring-substituted trans-2-(indol-3-yl)cyclopropylamine derivatives was synthesized and tested for affinity at the 5-HT1A receptor, by competition with [3H]-8-OH-DPAT in rat hippocampal homogenates, and for affinity at the agonist-labeled cloned human 5-HT2A, 5-HT2B, and 5-HT2C receptor subtypes. None of the compounds had high affinity for the 5-HT1A receptor, with the 5-methoxy substitution being most potent (40 nM)

  通过与大鼠海马匀浆中的[3H] -8-OH-DPAT竞争，合成了一系列四个外消旋的环取代的反式-2-（吲哚-3-基）环丙胺衍生物，并测试了对5-HT1A受体的亲和力。以及对激动剂标记的克隆人5-HT2A，5-HT2B和5-HT2C受体亚型的亲和力。没有一种化合物对5-HT1A受体具有高亲和力，其中5-甲氧基取代最有效（40 nM）。在5-HT2A和5-HT2B受体同工型中，大多数化合物缺乏高亲和力。但是，在5-HT2C受体上，亲和力要高得多。5-氟取代的化合物最有效，5-HT2C受体的Ki为1.9 nM。另外，还对未取代化合物的1R，2S-（-）和1S，2R-（+）对映异构体在5-HT 2同工型下进行了评估。而1R 2S对映异构体在5-HT2A和5-HT2B位点具有较高的亲和力，而1S，2R异构体在5-HT2C受体上具有最高的亲和力。立体选择性的这种逆转可以导致选择性5-HT 2C受体激动
• Enantioselective N-Heterocyclic Carbene Catalyzed Diene Regenerative (4 + 2) Annulation
  作者：Alison Levens、Changhe Zhang、Lisa Candish、Craig M. Forsyth、David W. Lupton

  DOI：10.1021/acs.orglett.5b02693

  日期：2015.11.6

  An enantioselective N-heterocyclic carbene (NHC)-catalyzed diene regenerative (4 + 2) annulation has been achieved through the use of highly nucleophilic morpholinone-derived catalysts. The reaction proceeds with good to excellent yields, high enantioselectivity (most >92% ee), and good diastereoselectivity (most >7:1). The generality of the reaction is high, with 19 examples reported. The utility

  通过使用高度亲核的吗啉酮衍生的催化剂，实现了对映选择性的N-杂环卡宾（NHC）催化的二烯再生（4 + 2）环化反应。该反应以良好至优异的收率，高对映选择性（大多数> 92％ee）和良好的非对映选择性（大多数> 7：1）进行。该反应的普遍性很高，报道了19个实例。产品的效用已经过检验，随后使用贫电子的亲二烯体在Diels-Alder反应中进行了衍生化处理。此外，已经实现了对所提出的β-内酯中间体的拦截，从而允许合成具有四个对映体和非对映体选择性的，具有四个连续立体中心的化合物。
• Phosphate transport inhibitors
  申请人：Jozefiak H. Thomas

  公开号：US20070021509A1

  公开（公告）日：2007-01-25

  Disclosed are compounds which have been identified as inhibitors of phosphate transport. Many of the compounds are represented by Structural Formula (I): Ar 1 —W—X—Y—Ar 2 ; or a pharmaceutically acceptable salt thereof. Ar 1 and Ar 2 are independently a substituted or unsubstituted aryl group or an optionally substituted five membered or six membered non-aromatic heterocylic group fused to an optionally substituted monocylic aryl group. W and Y are independently a covalent bond or a C1-C3 substituted or unsubstituted alkylene group. X is a heteroatom-containing functional group, an aromatic heterocyclic group, substituted aromatic heterocyclic group, non-aromatic heterocyclic group, substituted non-aromatic heterocyclic group, an olefin group or a substituted olefin group. Also disclosed are methods of treating a subject with a disease associated with hyperphosphatemia, as well as a disease mediated by phosphate-transport function. The methods comprise the step of administering an effective amount of the one of the compounds described above.

  本发明涉及已被鉴定为磷酸盐转运抑制剂的化合物。其中许多化合物由结构式（I）表示：Ar1-W-X-Y-Ar2；或其药学上可接受的盐。其中，Ar1和Ar2独立地为取代或未取代的芳基团或可选取代的五元或六元非芳基杂环团与可选取代的单环芳基团融合。W和Y独立地为共价键或C1-C3取代或未取代的烷基链。X为含杂原子的官能团、芳基杂环团、取代的芳基杂环团、非芳基杂环团、取代的非芳基杂环团、烯烃基或取代的烯烃基。本发明还涉及治疗与高磷血症相关的疾病以及由磷酸盐转运功能介导的疾病的方法。该方法包括给予上述化合物之一的有效量。
• The Total Synthesis of (+)-Hapalindole Q by an Organomediated Diels−Alder Reaction
  作者：Aaron C. Kinsman、Michael A. Kerr

  DOI：10.1021/ja036191y

  日期：2003.11.1

  The total synthesis of (+)-hapalindole Q has been achieved. The key step is a Diels-Alder reaction mediated by MacMillan's organocatalyst to provide the critical intermediate with high enantioselectivity (93% ee). This step establishes the proper arrangement of the required four contiguous stereocenters, including the quaternary center, and represents the first successful application of an enantioselective organomediated Diels-Alder reaction in total synthesis.
• Stereoselective Synthesis of trans-2-(Indol-3-yl)cyclopropylamines: Rigid Tryptamine Analogs
  作者：Suwanna Vangveravong、David E. Nichols

  DOI：10.1021/jo00116a028

  日期：1995.6

  A procedure for the preparation of trans-2-(indol-3-yl)cyclopropylamines is reported. The key step in the sequence is a stereoselective palladium-catalyzed cyclopropanation of the indole-3-acryloyl derivative of Oppolzer's chiral sultam (bornane[10,2]sultam) with diazomethane, following by the purification of the resulting diastereomeric cyclopropanated sultams by recrystallization. Base hydrolysis of the pure crystalline diastereomers gave the resolved indolylcyclopropane carboxylic acids. These could be converted into enantiomers of indolylcyclopropylamine by Curtius rearrangement, which did not affect the absolute configuration. In addition, single crystal X-ray erystallography of the cyclopropanated sultam was used to determine the absolute configuration of the intermediate indolylcyclopropanecarboxylic acid and thus to establish the configuration of the final compound.