α-(2-thiazolyl)diphenylmethanol | 42074-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-(2-thiazolyl)diphenylmethanol
• 英文别名: diphenyl(thiazol-2-yl)methanol；diphenyl(1,3-thiazol-2-yl)methanol；Phenyl-2-thiazol-phenylcarbinol；Diphenyl--carbinol
• CAS: 42074-46-4
• 化学式: C₁₆H₁₃NOS
• 分子量: 267.351
• InChiKey: KRGNAMUKMAQCFV-UHFFFAOYSA-N

物化性质

• 熔点：
  112 °C(Solv: ligroine (8032-32-4); ethyl ether (60-29-7))
• 沸点：
  447.8±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-(2-thiazolyl)diphenylmethanol 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以73%的产率得到α-(2-thiazolyl)diphenylmethane
  参考文献：
  名称：

  REDUCTION OF 1,3-AZOLE AND 1,3-BENZAZOLE CARBINOLS WITH SODIUM BOROHYDRIDE-TRIFLUOROACETIC ACID

  摘要：

  DOI：

  10.1080/00304949709355204
• 作为产物：
  描述：

  二苯甲酮 、 2-thiazolyl magnesium bromide 以 乙醚 、 苯 为溶剂， 生成 α-(2-thiazolyl)diphenylmethanol
  参考文献：
  名称：

  N-三取代甲基咪唑类作为抗真菌剂。

  摘要：

  DOI：

  10.1002/jps.2600620514

文献信息

• Programmed synthesis of arylthiazoles through sequential C–H couplings
  作者：Satoshi Tani、Takahiro N. Uehara、Junichiro Yamaguchi、Kenichiro Itami

  DOI：10.1039/c3sc52199k

  日期：——

  A programmed synthesis of privileged arylthiazoles via sequential C–H couplings catalyzed by palladium or nickel catalysts has been accomplished. This versatile protocol can supply all possible arylthiazole substitution patterns (2-aryl, 4-aryl, 5-aryl, 2,4-diaryl, 2,5-diaryl, 4,5-diaryl, and 2,4,5-triaryl) from an unfunctionalized thiazole platform by 11 distinct synthetic routes. We have generated

  特权arylthiazoles的编程合成通过由钯或镍催化剂催化顺序C-H偶合已经完成。该通用协议可提供所有可能的芳基噻唑取代方式（2-芳基，4-芳基，5-芳基，2,4-二芳基，2,5-二芳基，4,5-二芳基和2,4,5-三芳基）通过11种不同的合成途径从未官能化的噻唑平台上合成 使用这种方法，我们已经生成了150多种芳基噻唑。我们已经将该方法应用于脂肪抑制素（SREBP抑制剂）的快速合成，并且已证明克级合成三芳基噻唑。
• Generation and Reactions of Heteroaromatic Lithium Compounds by Using In-Line Mixer in a Continuous Flow Microreactor System at Mild Conditions
  作者：Binjie Liu、Yong Fan、Xiaoming Lv、Xiaofeng Liu、Yongtai Yang、Yu Jia

  DOI：10.1021/op300205j

  日期：2013.1.18

  lithium–halogen exchange reaction procedure was applied to introduce electrophilic substituents to the heteroaromatics, which exhibited potential in the syntheses of pharmaceutical intermediates. In this contribution, generation and reactions of heteroaromatic lithium compounds were successfully accomplished at 10 °C in a continuous flow microreactor equipped with an in-line mixer. Extensive reaction results revealed

  应用锂-卤素交换反应程序将亲电子取代基引入杂芳族化合物，该杂化剂在合成药物中间体中具有潜力。在这种贡献下，杂芳族锂化合物的生成和反应在配备了在线混合器的连续流动微反应器中于10°C下成功完成。广泛的反应结果表明，这种合成方法广泛适用于具有各种取代基的不同种类的杂芳族化合物。所有结果都表明，微反应器系统可以实现大规模合成的锂-卤素交换反应。
• Direct Amination of Azoles via Catalytic C−H, N−H Coupling
  作者：Daiki Monguchi、Taiki Fujiwara、Hirotoshi Furukawa、Atsunori Mori

  DOI：10.1021/ol900298e

  日期：2009.4.2

  C-H, N-H Coupling of azoles takes place with several amines in the presence of a copper catalyst to undergo amination at the 2-position. The reaction of benzothiazole with N-methylaniline in the presence of sodium acetate and 20 mol % Cu(OAc)(2) in xylene under an oxygen atmosphere afforded the aminated product in 81% yield.
• Copper-catalyzed oxidative C‒H, N‒H coupling of azoles and thiophenes
  作者：Shinobu Mitsuda、Taiki Fujiwara、Katsuyoshi Kimigafukuro、Daiki Monguchi、Atsunori Mori

  DOI：10.1016/j.tet.2012.03.001

  日期：2012.5

  C-H, N-H coupling of azole and thiophene derivatives takes place in the presence of a catalytic amount of Cu(OAc)(2) and an additive. The reaction of azoles smoothly occurs with several amines and amides catalyzed by 20 mol % of Cu(OAc)(2)-2PPh(3) and 4 equiv of NaOAc under O-2 or in the presence of Ag2CO3 under N-2. The coupling reaction leads to a facile synthesis of a N-substituted analogue of 2,5-diarylthiazole, which shows photoluminescent properties with extended pi-conjugation. Spectroscopic characteristics of the obtained thiazole derivatives are discussed by measurements of UV-vis absorption and photoluminescent spectra. Under the reaction conditions using Ag2CO3 as an additive and Cu(OAc)2-2PPh3 as a catalyst, thiophene derivatives also react with 2-pyrrolidone to undergo C-H, N-H amidation. (C) 2012 Elsevier Ltd. All rights reserved.
• Optimized <i>S</i>-Trityl-<scp>l</scp>-cysteine-Based Inhibitors of Kinesin Spindle Protein with Potent in Vivo Antitumor Activity in Lung Cancer Xenograft Models
  作者：James A. D. Good、Fang Wang、Oliver Rath、Hung Yi Kristal Kaan、Sandeep K. Talapatra、Dawid Podgórski、Simon P. MacKay、Frank Kozielski

  DOI：10.1021/jm3014597

  日期：2013.3.14

  The mitotic kinesin Eg5 is critical for the assembly of the mitotic spindle and is a promising chemotherapy target. Previously, we identified S-trityl-L-cysteine as a selective inhibitor of Eg5 and developed triphenylbutanamine analogues with improved potency, favorable drug-like properties, but moderate in vivo activity. We report here their further optimization to produce extremely potent inhibitors of Eg5 (K-i(app) < 10 nM) with broad-spectrum activity against cancer cell lines comparable to the Phase II drug candidates ispinesib and SB-743921. They have good oral bioavailability and pharmacolcinetics and induced complete tumor regression in nude mice explanted with lung cancer patient xenografts. Furthermore, they display fewer liabilities with CYP-metabolizing enzymes and hERG compared with ispinesib and SB-743921, which is important given the likely application of Eg5 inhibitors in combination therapies. We present the case for this preclinical series to be investigated in single and combination chemotherapies, especially targeting hematological malignancies.