(4S)-5,5-dimethyl-3-[(Z,2R)-2-methyl-4-phenylmethoxybut-3-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one | 1393834-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-5,5-dimethyl-3-[(Z,2R)-2-methyl-4-phenylmethoxybut-3-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 1393834-08-6
• 化学式: C₂₀H₂₇NO₄
• 分子量: 345.439
• InChiKey: CKHKVJJTJIXJIC-IHCBKXQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-5,5-dimethyl-3-[(Z,2R)-2-methyl-4-phenylmethoxybut-3-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one 在 双氧水 、 lithium hydroxide 、 potassium hydrogensulfate 、 sodium sulfite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.3h， 以70%的产率得到(Z,2S)-2-methyl-4-phenylmethoxybut-3-enoic acid
  参考文献：
  名称：

  Diastereoselective alkylations of oxazolidinone vinylogous glycolates

  摘要：

  A highly Z-selective isomerization (double bond migration) was observed when oxazolidinone vinylogous glycolate was exposed to a strong base to give N-acyl oxazolidinone, bearing an electron rich olefin. The corresponding enolate was exposed to alkyl halides to provide alkylated compounds on the gamma-position with respect to OBn group, with high regioselectivity and moderate diastereoselectivity. However, the nature of the chiral oxazolidinone leads to a significant increase in the reaction diastereoselectivity. A stereospecific formation of cis-olefin was also observed in these alkylated compounds. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.133
• 作为产物：
  描述：

  4-benzyloxy-but-2-enoic acid ethyl ester 在 三甲基乙酰氯 、 双(三甲基硅烷基)氨基钾 、 lithium chloride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 43.5h， 生成 (4S)-5,5-dimethyl-3-[(Z,2R)-2-methyl-4-phenylmethoxybut-3-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Diastereoselective alkylations of oxazolidinone vinylogous glycolates

  摘要：

  A highly Z-selective isomerization (double bond migration) was observed when oxazolidinone vinylogous glycolate was exposed to a strong base to give N-acyl oxazolidinone, bearing an electron rich olefin. The corresponding enolate was exposed to alkyl halides to provide alkylated compounds on the gamma-position with respect to OBn group, with high regioselectivity and moderate diastereoselectivity. However, the nature of the chiral oxazolidinone leads to a significant increase in the reaction diastereoselectivity. A stereospecific formation of cis-olefin was also observed in these alkylated compounds. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.133