methyl (Z)-4-[bromo(methoxyimino)methyl]benzoate | 159523-22-5

• 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: methyl (Z)-4-[bromo(methoxyimino)methyl]benzoate
• 英文别名: methyl 4-(C-bromo-N-methoxycarbonimidoyl)benzoate；methyl 4-[(Z)-C-bromo-N-methoxycarbonimidoyl]benzoate
• CAS: 159523-22-5
• 化学式: C₁₀H₁₀BrNO₃
• 分子量: 272.098
• InChiKey: RRGCWDPVNAFHAN-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (Z)-4-[bromo(methoxyimino)methyl]benzoate 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成 methyl (Z)-4-[2-hydroxy-1-(methoxyimino)-3-butenyl]benzoate
  参考文献：
  名称：

  Imino 1,2-Wittig rearrangement of hydroximates and its application to synthesis of cytoxazone

  摘要：

  The imino 1,2-Wittig rearrangement of hydroximates provides a novel method for the construction of 2-hydroxyoxime ethers. Upon treatment with LDA, Z-hydroximates smoothly underwent stereoselective rearrangement to give Z-2-hydroxyoxime ethers in good yield, which were converted into amino alcohols. On the other hand, the rearrangement of E-hydroximates gave a mixture of E- and Z-2-hydroxyoxime ethers. This method was successfully applied to a practical synthesis of cytoxazone. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.048
• 作为产物：
  描述：

  4-氯甲酰基苯甲酸甲酯 在 吡啶 、 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 methyl (Z)-4-[bromo(methoxyimino)methyl]benzoate
  参考文献：
  名称：

  Imino 1,2-Wittig rearrangement of hydroximates and its application to synthesis of cytoxazone

  摘要：

  The imino 1,2-Wittig rearrangement of hydroximates provides a novel method for the construction of 2-hydroxyoxime ethers. Upon treatment with LDA, Z-hydroximates smoothly underwent stereoselective rearrangement to give Z-2-hydroxyoxime ethers in good yield, which were converted into amino alcohols. On the other hand, the rearrangement of E-hydroximates gave a mixture of E- and Z-2-hydroxyoxime ethers. This method was successfully applied to a practical synthesis of cytoxazone. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.048

文献信息

• Imino 1,2-Wittig rearrangement of hydroximates and its application to synthesis of cytoxazone
  作者：Okiko Miyata、Tomoko Koizumi、Hiroshi Asai、Ryuichi Iba、Takeaki Naito

  DOI：10.1016/j.tet.2004.02.048

  日期：2004.4

  The imino 1,2-Wittig rearrangement of hydroximates provides a novel method for the construction of 2-hydroxyoxime ethers. Upon treatment with LDA, Z-hydroximates smoothly underwent stereoselective rearrangement to give Z-2-hydroxyoxime ethers in good yield, which were converted into amino alcohols. On the other hand, the rearrangement of E-hydroximates gave a mixture of E- and Z-2-hydroxyoxime ethers. This method was successfully applied to a practical synthesis of cytoxazone. (C) 2004 Elsevier Ltd. All rights reserved.