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 | 1248568-50-4

• 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-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
• CAS: 1248568-50-4
• 化学式: C₁₅H₁₈ClN₃O₅
• 分子量: 355.778
• InChiKey: ODCNZFRGFKXKRX-AUTRQRHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  tert-butyl (4S)-4-[4-[(1S,2S)-1-methoxy-2-methylbut-3-enyl]-1,3-oxazol-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 、 2-氯恶唑-4-甲酸 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 水 、 乙酸乙酯 、 二氯甲烷 为溶剂， 以77%的产率得到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
  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.