ethyl (Z)-3-[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenylmethoxybut-2-enoate | 1147271-11-1

• 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: ethyl (Z)-3-[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenylmethoxybut-2-enoate
• CAS: 1147271-11-1
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: ZEAQFWFYABKACC-BEAZESRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-3-[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenylmethoxybut-2-enoate 在 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 20.0h， 以88%的产率得到(2R)-2-[(1R)-1,2-dihydroxyethyl]-3-(phenylmethoxymethyl)-2H-furan-5-one
  参考文献：
  名称：

  Stereoselective synthesis of (+)-secosyrin 1

  摘要：

  A Chiron approach for the synthesis of (+)-secosyrin 1 from D-mannitol has been described. The key steps are a stereoselective Wittig reaction and an intramolecular Michael addition on the disubstituted butenolide, leading to a highly stereoselective formation of the tertiary chiral centre of (+)-secosyrin 1. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.106
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 ethyl (Z)-3-[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenylmethoxybut-2-enoate
  参考文献：
  名称：

  Stereoselective synthesis of (+)-secosyrin 1

  摘要：

  A Chiron approach for the synthesis of (+)-secosyrin 1 from D-mannitol has been described. The key steps are a stereoselective Wittig reaction and an intramolecular Michael addition on the disubstituted butenolide, leading to a highly stereoselective formation of the tertiary chiral centre of (+)-secosyrin 1. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.106

文献信息

• Stereoselective synthesis of (+)-secosyrin 1
  作者：D. Gautam、B. Venkateswara Rao

  DOI：10.1016/j.tetlet.2009.01.106

  日期：2009.4

  A Chiron approach for the synthesis of (+)-secosyrin 1 from D-mannitol has been described. The key steps are a stereoselective Wittig reaction and an intramolecular Michael addition on the disubstituted butenolide, leading to a highly stereoselective formation of the tertiary chiral centre of (+)-secosyrin 1. (C) 2009 Elsevier Ltd. All rights reserved.