(E)-(S)-2-Methyl-1-(2-methyl-oxazol-4-yl)-hexa-1,5-dien-3-ol | 202333-42-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-(S)-2-Methyl-1-(2-methyl-oxazol-4-yl)-hexa-1,5-dien-3-ol
• 英文别名: (1E,3S)-2-methyl-1-(2-methyl-1,3-oxazol-4-yl)hexa-1,5-dien-3-ol
• CAS: 202333-42-4
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: ICVUXOWVJDYFBQ-IOCXFXADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(S)-2-Methyl-1-(2-methyl-oxazol-4-yl)-hexa-1,5-dien-3-ol 在 咪唑 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 pyridine-SO3 complex 、 camphor-10-sulfonic acid 、 水 、 碘 、 sodium hexamethyldisilazane 、 二甲基亚砜 、 N-甲基吗啉氧化物 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 37.25h， 生成
  参考文献：
  名称：

  Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone B Analogues by the Macrolactonization Approach

  摘要：

  AbstractIn order to probe structure‐activity relationships in the epothilone area, two series of epothilone B analogues have been designed and synthesized. The first series containing an oxazole moiety in place of a thiazole on the side chain was constructed by utilizing key intermediates 7–9 or 10, 12, and 13 (Scheme 1), whereas the second series containing an ethano group instead of the gem‐dimethyl group at position 4 was synthesized from fragments 42 and 43. A Yamaguchi‐type macrolactonization reaction was used to construct the macrocycle from a secoacid, which was assembled, in both cases, by means of a) an aldol reaction, b) an Enders alkylation, and c) a Wittig‐type reaction. This convergent strategy provided access to oxazole analogues 2,4,29–32 and 4,4‐ethano derivatives 3,40,60–63 for biological studies.

  DOI：

  10.1002/chem.19970031212
• 作为产物：
  描述：

  2-甲基-3-[4-甲基(3,5-噁唑)]-2-丙醛 、 烯丙基溴化镁 在 (-)-B-methoxydiisopinocampheylborane 作用下， 生成 (E)-(S)-2-Methyl-1-(2-methyl-oxazol-4-yl)-hexa-1,5-dien-3-ol
  参考文献：
  名称：

  Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone A Analogues by the Olefin Metathesis Approach

  摘要：

  AbstractFor structure‐activity relationship studies, two series of epothilone A (1) analogues have been designed and synthesized, one containing an oxazole moiety instead of the thiazole heterocycle and the other containing a spirocyclopropane moiety in place of the gem‐dimethyl group at position C‐4 (4,4‐ethano‐epothilones). The olefin metathesis strategy in solution was utilized for the chemical synthesis of these compounds starting with key building blocks 7–9 for the oxazole series (compounds 2, 14–18, 21–26) and building blocks 8, 30, and 31 for the 4,4‐ethano series (compounds 3,39–43, 46–51). The convergent strategy towards the designed epothilone A series involved a) an aldol condensation reaction, b) an esterification reaction, c) an olefin metathesis reaction catalyzed by [RuCl2(=CHPh)‐(PCy3)2], and d) epoxidation of the macrocycle double bond.

  DOI：

  10.1002/chem.19970031211

文献信息

• US7173137B2
  申请人：——

  公开号：US7173137B2

  公开（公告）日：2007-02-06
• Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone A Analogues by the Olefin Metathesis Approach
  作者：K. C. Nicolaou、Hans Vallberg、N. Paul King、Frank Roschangar、Yun He、Dionisios Vourloumis、Christopher G. Nicolaou

  DOI：10.1002/chem.19970031211

  日期：1997.12

  AbstractFor structure‐activity relationship studies, two series of epothilone A (1) analogues have been designed and synthesized, one containing an oxazole moiety instead of the thiazole heterocycle and the other containing a spirocyclopropane moiety in place of the gem‐dimethyl group at position C‐4 (4,4‐ethano‐epothilones). The olefin metathesis strategy in solution was utilized for the chemical synthesis of these compounds starting with key building blocks 7–9 for the oxazole series (compounds 2, 14–18, 21–26) and building blocks 8, 30, and 31 for the 4,4‐ethano series (compounds 3,39–43, 46–51). The convergent strategy towards the designed epothilone A series involved a) an aldol condensation reaction, b) an esterification reaction, c) an olefin metathesis reaction catalyzed by [RuCl2(=CHPh)‐(PCy3)2], and d) epoxidation of the macrocycle double bond.
• Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone B Analogues by the Macrolactonization Approach
  作者：K. C. Nicolaou、Francisco Sarabia、M. Ray V. Finlay、Sacha Ninkovic、N. Paul King、Dionisios Vourloumis、Yun He

  DOI：10.1002/chem.19970031212

  日期：1997.12

  AbstractIn order to probe structure‐activity relationships in the epothilone area, two series of epothilone B analogues have been designed and synthesized. The first series containing an oxazole moiety in place of a thiazole on the side chain was constructed by utilizing key intermediates 7–9 or 10, 12, and 13 (Scheme 1), whereas the second series containing an ethano group instead of the gem‐dimethyl group at position 4 was synthesized from fragments 42 and 43. A Yamaguchi‐type macrolactonization reaction was used to construct the macrocycle from a secoacid, which was assembled, in both cases, by means of a) an aldol reaction, b) an Enders alkylation, and c) a Wittig‐type reaction. This convergent strategy provided access to oxazole analogues 2,4,29–32 and 4,4‐ethano derivatives 3,40,60–63 for biological studies.