2-chloro-4-[4-[4-[(1S,2S)-1-methoxy-2-methylbut-3-enyl]-1,3-oxazol-2-yl]-1,3-oxazol-2-yl]-1,3-oxazole | 1248568-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-chloro-4-[4-[4-[(1S,2S)-1-methoxy-2-methylbut-3-enyl]-1,3-oxazol-2-yl]-1,3-oxazol-2-yl]-1,3-oxazole
• CAS: 1248568-51-5
• 化学式: C₁₅H₁₄ClN₃O₄
• 分子量: 335.747
• InChiKey: JNXGFPLEHIQAKU-UFBFGSQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-chloro-4-[4-[4-[(1S,2S)-1-methoxy-2-methylbut-3-enyl]-1,3-oxazol-2-yl]-1,3-oxazol-2-yl]-1,3-oxazole 、 三丁基乙烯基锡 在 四氧化锇 、 N-甲基吗啉氧化物 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium periodate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 、 1,4-二氧六环 、 乙醇 为溶剂， 以73%的产率得到(2R,3S)-3-[2-[2-(2-ethenyl-1,3-oxazol-4-yl)-1,3-oxazol-4-yl]-1,3-oxazol-4-yl]-3-methoxy-2-methylpropanal
  参考文献：
  名称：

  Synthetic studies of mycalolide B, an actin-depolymerizing marine macrolide: construction of the tris-oxazole macrolactone using ring-closing metathesis

  摘要：

  Tris-oxazole macrolactone 2, a key intermediate of mycalolide B (1), which has 13 stereogenic centres, was synthesized through the use of ring-closing metathesis (RCM). The E/Z ratio of the RCM product 2 was reversed by the use of CH(2)Cl(2) and toluene, whereas a cross-metathesis reaction yielded the C1-C35 long-chain compound 19 in a highly E-selective manner. Thus, the loss of flexibility in aliphatic carbon chains and the steric hinderance of beta- and gamma-substituents of the C20 olefin in the precursor 11 may affect the stereoselectivity in RCM reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.046
• 作为产物：
  描述：

  2-chloro-N-[(1S)-2-hydroxy-1-[4-[(1S,2S)-1-methoxy-2-methylbut-3-enyl]-1,3-oxazol-2-yl]ethyl]-1,3-oxazole-4-carboxamide 在 二乙胺基三氟化硫 、 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2-chloro-4-[4-[4-[(1S,2S)-1-methoxy-2-methylbut-3-enyl]-1,3-oxazol-2-yl]-1,3-oxazol-2-yl]-1,3-oxazole
  参考文献：
  名称：

  Synthetic studies of mycalolide B, an actin-depolymerizing marine macrolide: construction of the tris-oxazole macrolactone using ring-closing metathesis

  摘要：

  Tris-oxazole macrolactone 2, a key intermediate of mycalolide B (1), which has 13 stereogenic centres, was synthesized through the use of ring-closing metathesis (RCM). The E/Z ratio of the RCM product 2 was reversed by the use of CH(2)Cl(2) and toluene, whereas a cross-metathesis reaction yielded the C1-C35 long-chain compound 19 in a highly E-selective manner. Thus, the loss of flexibility in aliphatic carbon chains and the steric hinderance of beta- and gamma-substituents of the C20 olefin in the precursor 11 may affect the stereoselectivity in RCM reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.046

文献信息

• Synthetic studies of mycalolide B, an actin-depolymerizing marine macrolide: construction of the tris-oxazole macrolactone using ring-closing metathesis
  作者：Masaki Kita、Hidekazu Watanabe、Tomoya Ishitsuka、Yuzo Mogi、Hideo Kigoshi

  DOI：10.1016/j.tetlet.2010.07.046

  日期：2010.9

  Tris-oxazole macrolactone 2, a key intermediate of mycalolide B (1), which has 13 stereogenic centres, was synthesized through the use of ring-closing metathesis (RCM). The E/Z ratio of the RCM product 2 was reversed by the use of CH(2)Cl(2) and toluene, whereas a cross-metathesis reaction yielded the C1-C35 long-chain compound 19 in a highly E-selective manner. Thus, the loss of flexibility in aliphatic carbon chains and the steric hinderance of beta- and gamma-substituents of the C20 olefin in the precursor 11 may affect the stereoselectivity in RCM reactions. (C) 2010 Elsevier Ltd. All rights reserved.