2-benzyloxy-4-methyl-4H-thiazol-5-one | 41893-30-5

• 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: 2-benzyloxy-4-methyl-4H-thiazol-5-one
• 英文别名: 4-methyl-2-phenylmethoxy-4H-1,3-thiazol-5-one
• CAS: 41893-30-5
• 化学式: C₁₁H₁₁NO₂S
• 分子量: 221.28
• InChiKey: IBFRRWVILQPIQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzyloxy-4-methyl-4H-thiazol-5-one 在 碘 、 三乙胺 作用下， 生成 N-benzylsulfanylcarbonyl-DL-alanine
  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
• 作为产物：
  描述：

  N-benzyloxythiocarbonyl-alanine 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-benzyloxy-4-methyl-4H-thiazol-5-one
  参考文献：
  名称：

  Siemion,I.Z. et al., Roczniki Chemii, 1972, vol. 46, p. 21 - 26

  摘要：

  DOI：

文献信息

• Highly <i>E</i> ‐Selective and Enantioselective Michael Addition to Electron‐Deficient Internal Alkynes Under Chiral Iminophosphorane Catalysis
  作者：Daisuke Uraguchi、Kohei Yamada、Takashi Ooi

  DOI：10.1002/anie.201503928

  日期：2015.8.17

  A highly E‐selective and enantioselective conjugate addition of 2‐benzyloxythiazol‐5(4H)‐ones to β‐substituted alkynyl N‐acyl pyrazoles is achieved under the catalysis of a P‐spiro chiral iminophosphorane. Simultaneous control of the newly generated central chirality and olefin geometry is possible with a wide array of the alkynyl Michael acceptors possessing different aromatic and aliphatic β‐substituents

  高度E-选择性和对映选择性共轭加成2- benzyloxythiazol -5（4H） -酮的对β-取代的炔基N-酰基吡唑是一种催化下实现P -螺手性膦亚胺。可以同时控制具有多种不同芳族和脂族β取代基以及各种α-氨基酸衍生的噻唑酮亲核基团的炔基Michael受体，从而同时控制新生成的中心手性和烯烃的几何形状。通过该协议，可以访问结构多样的旋光性α-氨基酸，在α-位置带有几何定义的三取代烯烃组分。
• Primary amine catalyzed diastereo- and enantioselective Michael reaction of thiazolones and α,β-unsaturated ketones
  作者：Min Lu、Hong Li、Chuncheng Zou、Jianchang Li、Chengyu Liu、Maolin Sun、Yueyue Ma、Ruihua Cheng、Jinxing Ye

  DOI：10.1039/c9ob02067e

  日期：——

  The chiral primary amine catalyzed asymmetric Michael reaction of thiazolones and α,β-unsaturated ketones was reported. Two different optimal catalytic systems were obtained corresponding to cyclic and linear α,β-unsaturated ketones. By employing chiral primary amines as the catalysts and amino-acid derivatives as the additives, a variety of Michael adducts containing the scaffold of the thiazole ring

  报道了手性伯胺催化噻唑酮与α，β-不饱和酮的不对称迈克尔反应。获得了对应于环状和线性α，β-不饱和酮的两种不同的最佳催化体系。通过使用手性伯胺作为催化剂和氨基酸衍生物作为添加剂，可以制备各种含有噻唑环骨架的迈克尔加合物，并具有中等至良好的收率，并具有出色的非对映和对映选择性（高达95％的收率，全部达到> 19/1 dr，最高达到96％ee）。扩大反应规模以获得1.73克迈克尔加合物，同时保持产率和立体选择性。
• Konopinska,D. et al., Roczniki Chemii, 1973, vol. 47, p. 35 - 42
  作者：Konopinska,D. et al.

  DOI：——

  日期：——
• Siemion,I.Z. et al., Roczniki Chemii, 1972, vol. 46, p. 29 - 37
  作者：Siemion,I.Z. et al.

  DOI：——

  日期：——