(Z)-4-benzylidene-2-phenylthiazol-5(4H)-one | 82865-29-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-4-benzylidene-2-phenylthiazol-5(4H)-one
• 英文别名: 4-((Z)-benzylidene)-2-phenyl-4H-thiazol-5-one；4-((Z)-Benzyliden)-2-phenyl-4H-thiazol-5-on；2-Thiazolin-5-one, 4-benzylidene-2-phenyl-；(4Z)-4-benzylidene-2-phenyl-1,3-thiazol-5-one
• CAS: 82865-29-0
• 化学式: C₁₆H₁₁NOS
• 分子量: 265.335
• InChiKey: QAVDULXNCMMIPW-KAMYIIQDSA-N

物化性质

• 熔点：
  130-131 °C
• 沸点：
  428.6±48.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-4-benzylidene-2-phenylthiazol-5(4H)-one 以 二氯甲烷 为溶剂， 反应 72.0h， 以82%的产率得到2,6,9,12-tetraphenyl-3,10-dithia-1,8-diazadispiro[4.1.4⁷.1⁵]-dodeca-1,8-diene-4,11-dione
  参考文献：
  名称：

  (Z)-4-Aryliden-5(4H)-噻唑酮的反应性：[2 + 2]-光环加成、开环反应以及路易斯酸 BF3 的影响

  摘要：

  ( Z )-2-苯基-4-亚芳基-5(4 H )-噻唑啉酮2在 CH 2 Cl 2溶液中用蓝光 (465 nm) 照射促进环外 C=C 的 [2 + 2]-光环加成键和二螺环丁烷的形成3 。该反应以高立体选择性发生，在大多数情况下，ε-异构体（1,3 头尾顺式偶联）的产率超过 90%。然而，在BF 3 ·OEt 2存在下，用蓝光（456 nm）在干燥MeOH中照射5(4 H )-噻唑啉酮2产生具有完全立体选择性的单螺环丁烷4 ，也提供ε-异构体。 4在甲醇解时似乎仅发生了一个噻唑酮环的开环反应，产生相应的酯和硫代酰胺基团。用醇中的碱 (NaOR/ROH) 处理游离的 4-亚芳基-5(4 H )-噻唑啉酮2也会通过甲醇解产生杂环的开环反应，尽管在这些反应条件下，进一步的分子内 S-观察到环外 C(H)=C 键的攻击并环化，形成具有高非对映异构体过量的顺式( RS / SR ) 和反式( RR

  DOI：

  10.1021/acs.joc.1c01458
• 作为产物：
  描述：

  4-苄基-2-苯基-4H-1,3-噻唑-5-酮 在 potassium permanganate 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 36.33h， 生成 (Z)-4-benzylidene-2-phenylthiazol-5(4H)-one
  参考文献：
  名称：

  Synthesis of Symmetrical 2,2',4,4'-Tetrasubstituted [4,4'-Bithiazole]-5,5'(4H,4'H)-diones and Their Reactions with Some Nucleophiles.

  摘要：

  Symmetrical 2,2',4,4'-tetrasubstituted-[4,4'-bithiazole]-5,5'(4H,4'H)-diones were obtained in high yields by oxidation of 5(4H)-thiazolones by KMnO4 in acetic acid. In some cases, the isomeric 2.4'- and 2,2'-bithiazolones were also formed. Results from two crossover reactions were consistent with a free radical mechanism. Four series of thiazolones were prepared, each based on a different substituent at the 2-position; i.e., phenyl, ethoxy, ethyl and ethylthio. The effects of substituents on the isomer distributions of the dehydrodimers indicated that electronic factors were less important than steric factors. X-Ray crystallography established the structure of the dehydrodimer (4R*,4'R*)-2,2'-diethoxy-4,4'dibenzyl-[4,4'-bithiazole]-5,5'(4H,4'H)-dione. One stereoisomer of 2,2'diphenyl-4,4'-dimethyl-[4,4'-bithiazole]-5,5'(4H,4'H)-dione and a mixture of the stereoisomers of 2,2'-diphenyl-4,4'-dibenzyl-[4,4'-bithiazole]-5,5'(4H,4'K)-dione were treated with nucleophiles. The former gave imide derivatives of alpha,alpha'-dehydrodimeric amino acids when the nucleophile was L-alanine ethyl ester or I-butylamine. The structure of one of the reaction products, (4R*,5R*)-2,5-diphenyl-2-thiazoline-4-carboxylic acid piperidylamide, was established by X-ray crystallography. Treatment of stereoisomeric mixtures of 2,2'-diethoxy-4,4'-bithiazolones with HCl in benzene gave the corresponding racemic and meso bis-(N-carboxythioanhydride)s. A stereoisomeric mixture of the bis(N-carboxythioanhydride)s of leucine treated with glycine ethyl ester gave a bicyclic derivative of the alpha,alpha'-dehydrodimeric amino acid.

  DOI：

  10.3891/acta.chem.scand.51-1000

文献信息

• Improved Erlenmeyer Synthesis with 5-Thiazolone and Catalytic Mn(II) Acetate. Crystal Structure Confirmation of the Reaction Stereochemistry
  作者：Sosale Chandrasekhar、V. Mohana Rao

  DOI：10.1002/jhet.1921

  日期：2014.8

  the presence of the mild base Mn(II) acetate as catalyst in CH2Cl2 solution. This leads to the corresponding Erlenmeyer reaction products () in excellent yields in the case of aromatic aldehydes and moderate yields in others. The mildness of the reaction conditions is apparently enabled by the aromaticity of the (putative) intermediate thiazolone anion. The structure and stereochemistry (Z) of the product

  在CH 2 Cl 2溶液中，在作为催化剂的弱碱乙酸锰（II）的存在下，2-苯基噻唑啉-5-酮（5硫代内酯）与各种醛缩合。这导致相应的锥形反应产物（）（对于芳族醛而言）具有优异的收率，而对于其他醛类则具有中等收率。反应条件的温和性显然是由（假定的）中间噻唑酮阴离子的芳香性实现的。通过单晶X射线衍射证实了衍生自i- BuCHO的产物的结构和立体化学（Z）。这项研究克服了经典锥形合成的关键局限性，并且引入了相对无毒的乙酸锰（II）作为杂环化学中的试剂。
• Convenient access to β-substituted cysteines and β- and γ-mercapto prolines
  作者：Jacob C. Hansen、Marco Rabuffetti、Lennart Bunch

  DOI：10.1139/cjc-2022-0161

  日期：——

  Herein we describe a convenient method for the synthesis of the β-substituted Cys analogs 1a, b and trans-β-mercapto proline 1c, from their corresponding α,β-unsaturated-α-amino esters using p-methoxybenzyl mercaptan as the sulfur source. The intermediate β-thioethers are stable toward chromatographic purification, and after global deprotection the β-mercapto amino acids 1a–c are obtained in good to high yields (64%–99%).

  在此，我们介绍了一种以对甲氧基苄基硫醇为硫源，从相应的 α,β-不饱和-α-氨基酯合成 β-取代的 Cys 类似物 1a、b 和反式-β-巯基脯氨酸 1c 的简便方法。中间体 β硫醚对色谱纯化很稳定，经过全局脱保护后，可得到β-巯基氨基酸 1a-c，收率从好到高（64%-99%）。
• Behringer; Stein, Chemische Berichte, 1949, vol. 82, p. 209,212
  作者：Behringer、Stein

  DOI：——

  日期：——
• Reaction of 5(4h)-thiazolones with diazomethane
  作者：I. Arenal、M. Bernabé、O. Cuevas、E. Fernández Alvarez

  DOI：10.1016/s0040-4020(01)91909-x

  日期：1983.1
• Lur'e; Gazenko, Zhurnal Obshchei Khimii, 1952, vol. 22, p. 262,264; engl. Ausg. S. 321, 323
  作者：Lur'e、Gazenko

  DOI：——

  日期：——