2-苯基-3-噻吩甲醛; 3-甲酰基-2-苯基噻吩 | 38115-13-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-苯基-3-噻吩甲醛; 3-甲酰基-2-苯基噻吩
• 中文别名: 3-甲酰基-2-苯基噻吩
• 英文名称: 2-phenylthiophene-3-carbaldehyde
• 英文别名: 2-phenyl-thiophene-3-carbaldehyde
• CAS: 38115-13-8
• 化学式: C₁₁H₈OS
• mdl: MFCD01927364
• 分子量: 188.25
• InChiKey: XRPQDWNLPCJCMI-UHFFFAOYSA-N

物化性质

• 沸点：
  331℃
• 密度：
  1.207
• 闪点：
  124℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氨基-4-甲基嘧啶 、 2-苯基-3-噻吩甲醛; 3-甲酰基-2-苯基噻吩 生成 (E/Z)-4-(2-(2-phenylthiophen-3-yl)vinyl)pyrimidin-2-amine
  参考文献：
  名称：

  Discovery of imidazole vinyl pyrimidines as a novel class of kinase inhibitors which inhibit Tie-2 and are orally bioavailable

  摘要：

  Tie-2 is a receptor tyrosine kinase which is involved in angiogenesis and thereby growth of human tumours. The discovery and SAR of a novel class of imidazole-vinyl-pyrimidine kinase inhibitors, which inhibit Tie-2 in vitro is reported. Their synthesis was carried out by condensation of imidazole aldehydes with methyl pyrimidines. These compounds are lead-like, with low molecular weight, good physical properties and oral bioavailability. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.106
• 作为产物：
  描述：

  2-溴噻吩-3-甲醛 、 苯硼酸 在 potassium fluoride 、 palladium diacetate 、 2-二叔丁基膦-1-苯基吲哚 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以70%的产率得到2-苯基-3-噻吩甲醛; 3-甲酰基-2-苯基噻吩
  参考文献：
  名称：

  Highly Efficient and Versatile Synthesis of Polyarylfluorenes via Pd-Catalyzed C−H Bond Activation

  摘要：

  A facile protocol for the Pd-catalyzed preparative synthesis of fluorene derivatives has been developed. While a wide range of fluorenes; were easily obtained with high efficiency and selectivity under mild conditions, excellent functional group tolerance was also demonstrated. On the basis of Hammett and KIE studies, the present reaction is proposed to proceed via a base-assisted deprotonative metalation pathway.

  DOI：

  10.1021/ol901854f

文献信息

• COMPOUNDS OF PHOSPHINANES AND AZAPHOSPHINANES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：LES LABORATOIRES SERVIER

  公开号：US20180016288A1

  公开（公告）日：2018-01-18

  Compounds of formula (I) wherein: Ak 1 represents an alkyl chain, X represents —(CH 2 ) m —, —CH(R)—, —N(R)—, —CH 2 —N(R)—, —N(R)—CH 2 — or —CH 2 —N(R)—CH 2 —, m and R are as defined in the description, R 1 and R 2 each represent H when X represents —(CH 2 ) m —, —CH(R)—, —N(R)—, —CH 2 —N(R)— or —N(R)—CH 2 —, or together form a bond when X represents —CH 2 —N(R)—CH 2 —, R 3 represents NH 2 , Cy-NH 2 , Cy-Ak 3 -NH 2 or piperidin-4-yl, Cy and Ak 3 are as defined in the description, R 4 and R 5 , which may be identical or different, each represent H or F, their optical isomers, and addition salts thereof with a pharmaceutically acceptable acid. Medicinal products containing the same which are useful in treating conditions requiring a TAFIa inhibitor.

  式(I)的化合物中： Ak1代表一个烷基链， X代表—(CH2)m—，—CH(R)—，—N(R)—，—CH2—N(R)—，—N(R)—CH2—或—CH2—N(R)—CH2—， m和R如描述中所定义， R1和R2分别在X代表—(CH2)m—，—CH(R)—，—N(R)—，—CH2—N(R)—或—N(R)—CH2—时代表H， 或者当X代表—CH2—N(R)—CH2—时，它们一起形成一个键， R3代表NH2，Cy-NH2，Cy-Ak3-NH2或哌啶-4-基， Cy和Ak3如描述中所定义， R4和R5，可能相同也可能不同，每个代表H或F， 它们的光学异构体， 以及它们与药学上可接受的酸形成的盐。 包含这些化合物的药品，在治疗需要TAFIa抑制剂的情况下有用。
• Extension of the Heck reaction to the arylation of activated thiophenes
  作者：L. Lavenot、C. Gozzi、K. Ilg、I. Orlova、V. Penalva、M. Lemaire

  DOI：10.1016/s0022-328x(98)00667-6

  日期：1998.9

  The direct arylation of activated thiophenes was accomplished in moderate to good yields using a Heck-type reaction with the mixture of Pd(OAc)2 and n-Bu4NBr as a catalytic system. This new arylation method is applied to different derivatives and has proved to be compatible with sensitive functional groups. Furthermore, the substituent nature and position on the thiophene moiety influence the cross

  使用Heck型反应，将Pd（OAc）2和n- Bu 4 NBr的混合物作为催化体系，可以中等至良好的产率完成活化噻吩的直接芳基化反应。这种新的芳基化方法适用于不同的衍生物，并已证明与敏感的官能团兼容。此外，噻吩部分上的取代基性质和位置影响交叉偶联。特别是当杂环在第2位被吸电子基团取代时，该取代是区域特异性的。
• Direct thiophene arylation catalysed by palladium
  作者：Christel Gozzi、Laurence Lavenot、Kerstin Ilg、Vincent Penalva、Marc Lemaire

  DOI：10.1016/s0040-4039(97)10395-1

  日期：1997.12

  Direct thiophene arylation using a Heck-type reaction with as catalytic system is reported. Reactions with 2- and 3-substituted thiophenes have shown that substituent nature and position influence the cross-coupling. In particular, the substitution is regiospecific when the heterocycle is 2-substituted with an electron withdrawing group.

  报道了使用Heck型反应作为催化体系的直接噻吩芳基化。与2-和3-取代的噻吩的反应表明，取代基的性质和位置影响交叉偶联。特别地，当杂环被吸电子基团2-取代时，该取代是区域特异性的。
• Compounds of phosphinanes and azaphosphinanes, a process for their preparation and pharmaceutical compositions containing them
  申请人：LES LABORATOIRES SERVIER

  公开号：US10654878B2

  公开（公告）日：2020-05-19

  Compounds of formula (I) wherein: Ak1 represents an alkyl chain, X represents —(CH2)m—, —CH(R)—, —N(R)—, —CH2—N(R)—, —N(R)—CH2— or —CH2—N(R)—CH2—, m and R are as defined in the description, R1 and R2 each represent H when X represents —(CH2)m—, —CH(R)—, —N(R)—, —CH2—N(R)— or —N(R)—CH2—, or together form a bond when X represents —CH2—N(R)—CH2—, R3 represents NH2, Cy-NH2, Cy-Ak3-NH2 or piperidin-4-yl, Cy and Ak3 are as defined in the description, R4 and R5, which may be identical or different, each represent H or F, their optical isomers, and addition salts thereof with a pharmaceutically acceptable acid. Medicinal products containing the same which are useful in treating conditions requiring a TAFIa inhibitor.

  式(I)化合物 其中 Ak1 代表烷基链、 X 代表-(CH2)m-、-CH(R)-、-N(R)-、-CH2-N(R)-、-N(R)-CH2-或-CH2-N(R)-CH2-、 m 和 R 如说明中所定义、 当 X 代表-(CH2)m-、-CH(R)-、-N(R)-、-CH2-N(R)-或-N(R)-CH2-时，R1 和 R2 各自代表 H、 或当 X 代表-CH2-N(R)-CH2-时共同形成键、 R3 代表 NH2、Cy-NH2、Cy-Ak3-NH2 或哌啶-4-基、 Cy和Ak3如描述中所定义、 R4 和 R5 可以相同或不同，各自代表 H 或 F、 它们的光学异构体，以及它们与药学上可接受的酸的加成盐。 含有这些成分的医药产品可用于治疗需要 TAFIa 抑制剂的病症。
• Synthesis and evaluation of new arylbenzo[b]thiophene and diarylthiophene derivatives as inhibitors of the NorA multidrug transporter of Staphylococcus aureus
  作者：Jérémie Fournier dit Chabert、Béatrice Marquez、Luc Neville、Lionel Joucla、Sylvie Broussous、Pascale Bouhours、Emilie David、Stéphane Pellet-Rostaing、Bernard Marquet、Nicole Moreau、Marc Lemaire

  DOI：10.1016/j.bmc.2007.04.023

  日期：2007.7

  The synthesis based on palladium catalytic coupling of 38 new-arylated benzo[b]thiophenes or thiophenes is described in a few steps. We also report the direct arylation of the position 3 of the benzo[b]thiophenic structure, a 'one pot' 2,5-heterodiarylation of thiophenes as well as the synthesis of precursors of amino-acids with a 2-arylated benzo[b]thiophene core. These compounds were evaluated on bacteria strains: most of them did not exhibit any antibiotic activity but were found to selectively inhibit the NorA multidrug transporter of Staphylococcus aureus. As such, they restored the activity of the NorA substrates ciprofloxacin against a resistant S. aureus strain in which this efflux pump is over-expressed. (c) 2007 Elsevier Ltd. All rights reserved.