2-methyl-3-tosyl-1-propanol | 129665-60-7

• 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: 2-methyl-3-tosyl-1-propanol
• 英文别名: 1-tosyl-2-methyl-3-propanol；2-Methyl-3-(4-methylphenyl)sulfonylpropan-1-ol
• CAS: 129665-60-7
• 化学式: C₁₁H₁₆O₃S
• 分子量: 228.312
• InChiKey: XGXRKRMJHKPUOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-3-tosyl-1-propanol 在 copper(l) iodide 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 生成 tert-butyl (2S)-2-[(4-{[3-cyano-1-(2-methyl-3-(tosyloxy)propyl)-1H-indazol-5-yl]oxy}phenyl) carbamoyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  [¹⁸F]ZCDD083: A PFKFB3-Targeted PET Tracer for Atherosclerotic Plaque Imaging

  摘要：

  PFKFB3, a glycolysis-related enzyme upregulated in inflammatory conditions and angiogenesis, is an emerging target for diagnosis and therapy of atherosclerosis. The fluorinated phenoxindazole [F-18]ZCDD083 was synthesized, radiolabeled in 17 +/- 5% radiochemical yield and >99% radiochemical purity, and formulated for preclinical PET/CT imaging in mice. In vivo stability analysis showed no significant metabolite formation. Biodistribution studies showed high blood pool activity and slow hepatobiliary clearance. Significant activity was detected in the lung 2 h postinjection (pi) (11.0 +/- 1.5%ID/g), while at 6 h pi no pulmonary background was observed. Ex vivo autoradiography at 6 h pi showed significant high uptake of [F-18]ZCDD083 in the arch region and brachiocephalic artery of atherosclerotic mice, and no uptake in control mice, matching plaques distribution seen by lipid staining along with PFKFB3 expression seen by immunofluorescent staining. In vivo PET scans showed higher aortic region uptake of [F-18]ZCDD083 in atherosclerotic ApoE(-/-)Fbn1(C1039G+/-) than in control mice (0.78 +/- 0.05 vs 0.44 +/- 0.09%ID/g). [F-18]ZCDD083 was detected in aortic arch and brachiocephalic artery of ApoE(-/-) (with moderate atherosclerosis) and ApoE(-/-)Fbn1(C1039G+/-) (with severe, advanced atherosclerosis) mice, suggesting this tracer may be useful for the noninvasive detection of atherosclerotic plaques in vivo.

  DOI：

  10.1021/acsmedchemlett.9b00677
• 作为产物：
  描述：

  甲基碘化镁 、 2-(p-toluenesulfonylmethyl)oxirane 在 水 、 甲基氯化镁 、 氯化铵 、 copper(I) bromide 作用下， 生成 2-methyl-3-tosyl-1-propanol
  参考文献：
  名称：

  通过β，γ-环氧砜的区域选择性开环合成β-和γ-羟基砜

  摘要：

  衍生自烯丙基砜的β，γ-环氧砜1在有或没有催化量的溴化铜（I）存在下与有机镁化合物区域选择性反应，分别得到β-羟基砜2或γ-甲苯磺酸化的烯丙基醇化物5。在催化量的溴化铜（l）存在下，将格氏试剂的迈克尔类型加到中间体5会生成γ-羟基砜6。β-和γ-羟基砜的PCC氧化分别得到β-和γ-氧代砜10和11。对于γ-OXO砜，用DBU处理 得到α-取代的α，β-不饱和羰基化合物。

  DOI：

  10.1016/s0040-4020(01)90534-4

文献信息

• NAJERA, CARMEN;SANSANO, JOSE MIGUEL, TETRAHEDRON, 46,(1990) N1, C. 3993-4002
  作者：NAJERA, CARMEN、SANSANO, JOSE MIGUEL

  DOI：——

  日期：——
• [¹⁸F]ZCDD083: A PFKFB3-Targeted PET Tracer for Atherosclerotic Plaque Imaging
  作者：Carlo De Dominicis、Paola Perrotta、Sergio Dall’Angelo、Leonie Wyffels、Steven Staelens、G. R. Y. De Meyer、Matteo Zanda

  DOI：10.1021/acsmedchemlett.9b00677

  日期：2020.5.14

  PFKFB3, a glycolysis-related enzyme upregulated in inflammatory conditions and angiogenesis, is an emerging target for diagnosis and therapy of atherosclerosis. The fluorinated phenoxindazole [F-18]ZCDD083 was synthesized, radiolabeled in 17 +/- 5% radiochemical yield and >99% radiochemical purity, and formulated for preclinical PET/CT imaging in mice. In vivo stability analysis showed no significant metabolite formation. Biodistribution studies showed high blood pool activity and slow hepatobiliary clearance. Significant activity was detected in the lung 2 h postinjection (pi) (11.0 +/- 1.5%ID/g), while at 6 h pi no pulmonary background was observed. Ex vivo autoradiography at 6 h pi showed significant high uptake of [F-18]ZCDD083 in the arch region and brachiocephalic artery of atherosclerotic mice, and no uptake in control mice, matching plaques distribution seen by lipid staining along with PFKFB3 expression seen by immunofluorescent staining. In vivo PET scans showed higher aortic region uptake of [F-18]ZCDD083 in atherosclerotic ApoE(-/-)Fbn1(C1039G+/-) than in control mice (0.78 +/- 0.05 vs 0.44 +/- 0.09%ID/g). [F-18]ZCDD083 was detected in aortic arch and brachiocephalic artery of ApoE(-/-) (with moderate atherosclerosis) and ApoE(-/-)Fbn1(C1039G+/-) (with severe, advanced atherosclerosis) mice, suggesting this tracer may be useful for the noninvasive detection of atherosclerotic plaques in vivo.
• Synthesis of β- and γ-hydroxy sulfones by regioselective opening of β,γ-epoxy sulfones
  作者：Carmen Nájera、José Miguel Sansano

  DOI：10.1016/s0040-4020(01)90534-4

  日期：1990.1

  sulfones react regio-selectively with organomagnesium compounds in the presence or not of catalytic amounts of copper(I) bromide to afford β-hydroxy sulfones 2 or γ-tosylated allylic alcoholates 5 respectively. The Michael type addition of Grignard reagents to intermediates 5 in the presence of catalytic amount of copper(l) bromide yields γ-hydroxy sulfones 6. The PCC oxidation of β- and γ-hydroxy sulfones

  衍生自烯丙基砜的β，γ-环氧砜1在有或没有催化量的溴化铜（I）存在下与有机镁化合物区域选择性反应，分别得到β-羟基砜2或γ-甲苯磺酸化的烯丙基醇化物5。在催化量的溴化铜（l）存在下，将格氏试剂的迈克尔类型加到中间体5会生成γ-羟基砜6。β-和γ-羟基砜的PCC氧化分别得到β-和γ-氧代砜10和11。对于γ-OXO砜，用DBU处理 得到α-取代的α，β-不饱和羰基化合物。