4-methoxyphenyl(2-thienyl)methanol | 40310-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxyphenyl(2-thienyl)methanol
• 英文别名: α-[(4'-methoxyphenyl)]-2-thienylmethanol；α-(4-methoxyphenyl)-2-thiophenemethanol；(4-methoxy-phenyl)-thiophen-2-yl-methanol；(4-methoxyphenyl)-thiophen-2-ylmethanol
• CAS: 40310-33-6
• 化学式: C₁₂H₁₂O₂S
• 分子量: 220.292
• InChiKey: YDQODCKLZJJDCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl(2-thienyl)methanol 在 四氯化钛 、 三乙基硼氢化锂 、 N,N-二异丙基乙胺 作用下， 生成 (2R)-3-(4-methoxyphenyl)-2-methyl-3-thiophen-2-ylpropan-1-ol
  参考文献：
  名称：

  铟（III）盐的协同立体选择性有机催化

  摘要：

  摘要 铟（III）路易斯酸与水和胺的相容性使其可用于协同催化和协同催化。铟盐的存在促进了其中生成碳正离子的立体选择性有机催化S N 1型反应。可以在有机催化中利用铟盐的特殊性质来设计与水相容的，良性的，绿色的工艺。这种铟（III）促进的有机催化方法的发展是我们最近研究的重点，本文对此进行了总结。 铟（III）路易斯酸与水和胺的相容性使其可用于协同催化和协同催化。铟盐的存在促进了其中生成碳正离子的立体选择性有机催化S N 1型反应。可以在有机催化中利用铟盐的特殊性质来设计与水相容的，良性的，绿色的工艺。这种铟（III）促进的有机催化方法的发展是我们最近研究的重点，本文对此进行了总结。

  DOI：

  10.1055/s-0033-1341022
• 作为产物：
  描述：

  2-(4-甲氧基苄氧基)噻吩 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到4-methoxyphenyl(2-thienyl)methanol
  参考文献：
  名称：

  Krishnaswamy, N. R.; Kumar, Ch. Siva Sai Kamana; Prasanna, S., Journal of Chemical Research, Miniprint, 1991, # 7, p. 1801 - 1830

  摘要：

  DOI：

文献信息

• Thiophene containing triarylmethanes as antitubercular agents
  作者：Maloy Kumar Parai、Gautam Panda、Vinita Chaturvedi、Y.K. Manju、Sudhir Sinha

  DOI：10.1016/j.bmcl.2007.10.083

  日期：2008.1

  A new series of thiophene containing triarylmethane derivatives were synthesized from the Friedel-Crafts alkylation of diarylcarbinols followed by incorporation of amino alkyl chains. These were evaluated against Mycobacterium tuberculosis H37R(v) and showed the activity in the range of 3.12-12.5 microg/mL in vitro.

  由二芳基甲醇的弗瑞德-克来福特烷基化反应，然后结合氨基烷基链，合成了一系列新的含噻吩的三芳基甲烷衍生物。对它们进行了针对结核分枝杆菌H37R（v）的评估，并在体外显示其活性在3.12-12.5 microg / mL的范围内。
• Chemoselective C-Benzylation of Unprotected Anilines with Benzyl Alcohols Using Re₂O₇ Catalyst
  作者：Rajender Nallagonda、Mohammad Rehan、Prasanta Ghorai

  DOI：10.1021/jo4028598

  日期：2014.4.4

  An unprecedented dehydrative C–C bond formation between unprotected anilines with benzyl alcohols is disclosed. Re2O7 catalyst (5 mol %) at elevated reaction temperature (80 °C) provided C-benzylanilines with high to excellent yields and with good chemoselectivities (over N-alkylation). A probable mechanism has been proposed based on mechanistic studies.

  公开了未保护的苯胺与苄醇之间前所未有的脱水C-C键形成。再2 ö 7在提供升高的反应温度（80℃）催化剂（5摩尔％）Ç高到优异的产率-benzylanilines并具有良好的chemoselectivities（超过N-烷基化）。基于机理研究，提出了一种可能的机制。
• Porphyrin derivatives
  申请人：Yahioglu Gokhan

  公开号：US20070015742A1

  公开（公告）日：2007-01-18

  The present invention relates to a compound of formula (I): Formula (I) wherein one or two of A, B, C and D are each independently selected from S, O, Se and Te, and the remainder are N; a, b, c and d are each independently substituted or unsubstituted 5-membered heterocyclic groups having the members necessary to complete a porphyrin, chlorin, bacteriochlorin or isobacteriochlorin nucleus in which one or two of the nitrogens are replaced by S, O, Se or Te; M is H or a metal; R 1 , R 2 , R 3 and R 4 are each independently selected from: H; alkyl; cycloalkyl; halogen; aryl or heteroaryl, each of which may be optionally substituted by one or more substituents selected from OH, CN, CF 3 , alkyl, alkoxy, haloalkyl, halogen, an isothiocyanate group, a haloacetamide, maleimide, NH 2 , NO 2 , CONH 2 , COOH, COO-alkyl, —OZ, —COOZ, a polyethylene glycol group, an alkyl sulfonate group, an alkyl-COOH group, a substituted or unsubstituted benzyl group, a sugar derivative, —C≡C—(CH 2 ) p CO 2 R 10 , where R 10 is H or alkyl, and O(CH 2 ) r COR 11 , where R 11 , is OH, O-alkyl or —N-succinimide, and p and r are each independently an integer from 1 to 10; Formula (II) wherein W is an aryl, alkyl or heteroaryl group, each of which may be optionally substituted by one or more substituents listed above where Z is a silicon-containing protecting groups; and wherein when a, b, c and d have the members necessary to complete a porphyrin nucleus in which one or two of the nitrogens are replaced by S, O, Se or Te, (c) R 1 , R 2 and R 3 are identical, and R 4 ≠R 1 , R 2 , R 3 ; or (d) R 1 =R 3 ; R 2 =R 4 , where R 1 , R 3 ≠R 2 , R 4 ; or (d) R 2 =R 3 ; R 1 ≠R 4 ; and R 1 , R 4 ≠R 2 , R 3 .

  本发明涉及以下公式（I）的化合物：公式（I）其中A，B，C和D中的一个或两个分别独立地选择自S，O，Se和Te，其余为N; a，b，c和d分别是取代或未取代的5元杂环基团，其中包含完成卟啉，氯啉，细菌叶绿素或异细菌叶绿素核的必要成员，其中一或两个氮被S，O，Se或Te取代; M为H或金属; R1，R2，R3和R4分别选择自：H;烷基;环烷基;卤素;芳基或杂环芳基，每个可以选择性地被一个或多个取代基取代，所述取代基选择自OH，CN，CF3，烷基，烷氧基，卤代烷基，卤素，异硫氰酸酯基，卤代乙酰胺，马来酰亚胺，NH2，NO2，CONH2，COOH，COO-烷基，-OZ，-COOZ，聚乙二醇基团，烷基磺酸基团，烷基-COOH基团，取代或未取代的苯甲基基团，糖衍生物，-C≡C-（CH2）pCO2R10，其中R10为H或烷基，以及O（CH2）rCOR11，其中R11为OH，O-烷基或-N-琥珀酰亚胺，p和r分别是从1到10的整数; 公式（II）其中W是芳基，烷基或杂环芳基基团，每个可以选择性地被上述一个或多个取代基取代，其中Z是含硅保护基; 当a，b，c和d具有完成一或两个氮被S，O，Se或Te取代的卟啉核所需的成员时，（c）R1，R2和R3相同，R4≠R1，R2，R3; 或（d）R1 = R3; R2 = R4，其中R1，R3≠R2，R4; 或（d）R2 = R3; R1≠R4; 且R1，R4≠R2，R3。
• Boron Lewis Acid Catalysis Enables the Direct Cyanation of Benzyl Alcohols by Means of Isonitrile as Cyanide Source
  作者：Tong-Tong Xu、Jin-Lan Zhou、Guang-Yuan Cong、Jiang-Yi-Hui Sheng、Shi-Qi Wang、Yating Ma、Jian-Jun Feng

  DOI：10.3390/molecules28052174

  日期：——

  The development of an efficient and straightforward method for cyanation of alcohols is of great value. However, the cyanation of alcohols always requires toxic cyanide sources. Herein, an unprecedented synthetic application of an isonitrile as a safer cyanide source in B(C6F5)3-catalyzed direct cyanation of alcohols is reported. With this approach, a wide range of valuable α-aryl nitriles was synthesized

  开发一种有效且直接的醇氰化方法具有重要价值。然而，醇的氰化总是需要有毒的氰化物源。在此，报道了异腈作为更安全的氰化物源在 B(C6F5)3 催化的醇直接氰化中前所未有的合成应用。通过这种方法，以良好到极好的收率（高达 98%）合成了多种有价值的 α-芳基腈。反应可以放大，这种方法的实用性在抗炎药萘普生的合成中得到进一步体现。此外，还进行了实验研究来说明反应机理。
• Thiophene containing trisubstituted methanes [TRSMs] as identified lead against Mycobacterium tuberculosis
  作者：Priyanka Singh、Sudipta Kumar Manna、Amit Kumar Jana、Tiash Saha、Pankaj Mishra、Saurav Bera、Maloy Kumar Parai、Srinivas Lavanya Kumar M、Sankalan Mondal、Priyanka Trivedi、Vinita Chaturvedi、Shyam Singh、Sudhir Sinha、Gautam Panda

  DOI：10.1016/j.ejmech.2015.03.036

  日期：2015.5

  Triarylmethanes (TRAMs) and thiophene containing trisubstituted methanes (TRSMs) have been reported by us, having potential against Mycobacterium tuberculosis and Mycobacterium fortuitum strains, respectively. Further, extension through synthesis and biological evaluation of novel TRSMs resulted into an identified lead 36 (S006-830) [(diisopropyl-(2-4-[(4-methoxy-phenyl)- thiophen-2-yl-methyll-phenoxy}-ethyl)-amine)] with MIC: 1.33 mg/L, non-toxic against Vero C-1008 cell line with selectivity index >10, ex vivo efficacy equivalent to first line TB drugs-isoniazid (INH), rifampicin (RFM) and pyrazinamide (PZA) in the mouse and human macrophages, and lung CFU count of 2.2 x 10(7) (approximately 15 fold lesser than untreated mice, 31 x 10(7)) with efficacies comparable to ethambutol (EMB) (1.27 x 10(7)) and PZA (1.9 x 10(7)). Further, S006-830 also showed potent bactericidal activity against multi-drug resistant and single-drug resistant clinical isolates of M. tuberculosis. (C) 2015 Elsevier Masson SAS. All rights reserved.