5-bromo-4-(bromomethyl)-2-phenyl-1,3-oxazole | 101085-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-bromo-4-(bromomethyl)-2-phenyl-1,3-oxazole
• 英文别名: 5-bromo-4-bromomethyl-2-phenyloxazole；5-bromo-4-bromomethyl-2-phenyl-oxazole；5-Brom-4-brommethyl-2-phenyl-oxazol；Oxazole, 5-bromo-4-(bromomethyl)-2-phenyl-
• CAS: 101085-25-0
• 化学式: C₁₀H₇Br₂NO
• 分子量: 316.98
• InChiKey: DUPYWIOQNFWBMA-UHFFFAOYSA-N

物化性质

• 沸点：
  386.6±50.0 °C(Predicted)
• 密度：
  1.796±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-4-(bromomethyl)-2-phenyl-1,3-oxazole 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 (6S,7R)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-phenyl-5-(phenylsulfonyl)4,5,6,7-tetrahydro[1,3]oxazolo[4,5-c]pyridin-7-ol
  参考文献：
  名称：

  New Strategy for the Synthesis of Iminoglycitols from Amino Acids

  摘要：

  A novel strategy for the enantioselective synthesis of polyhydroxypiperidines, which can be considered as iminoglycitols or 2,6-dideoxyazasugars, was developed, alpha-Benzolsulfonylamino esters served as a C2N building block while 2-bromo-3-(bromomethyl)oxazoles and -thiazoles contributed a C3-unit to the final piperidine ring. At first a dihydropyridine ring was established via alkylation and bromine-lithium exchange. The keto group of the resulting 5,6-dihydro[1,3]oxazolo- and 5,6-dihydro[1,3]thiazolo[4,5-c]pyridin-7(4H)-ones was reduced and, after alkylation reactions, the azole ring was cleaved, thus providing heteroatom substituents for the target piperdines. Protected 5-amino-3,4-dihydroxy and 5-amino-3-hydroxy-4-thiohydroxypiperdines were obtained in the talose series while Mitsunobu reaction of the intermiediates provided access to the altrose series.

  DOI：

  10.1021/jo010665z
• 作为产物：
  描述：

  4-甲基-2-苯基-1,3-噁唑 在 溴 作用下， 生成 5-bromo-4-(bromomethyl)-2-phenyl-1,3-oxazole
  参考文献：
  名称：

  Gompper; Ruehle, Justus Liebigs Annalen der Chemie, 1959, vol. 626, p. 83,91

  摘要：

  DOI：

文献信息

• An all-cis 3,4-dihydroxy-5-aminopiperidine by a novel route to deoxydiamino sugars
  作者：Sauda Swaleh、Jürgen Liebscher

  DOI：10.1016/s0040-4039(99)00156-2

  日期：1999.3

  An (L)-diaza-1,6-dideoxytalose 7 as a first example of a new synthetic concept for aminodeoxy sugars by destruction of the 5-membered heterocyclic ring of condensed pyridones derived from natural amino acids and an o-bromo-bromomethyl 5-membered heterocycle is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.