(4S)-2-异丁基-4-异丙基-4,5-二氢-1,3-恶唑 | 175226-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: (4S)-2-异丁基-4-异丙基-4,5-二氢-1,3-恶唑
• 中文别名: 2-环丙烯-1-羧酸,2,3-二乙基-1-(三甲基甲硅烷基)-,甲基酯
• 英文名称: (4S)-2-(2-methylpropyl)-4-isopropyl-4,5-dihydrooxazole
• 英文别名: (S)-2-isobutyl-4-isopropyl-4,5-dihydrooxazole；(4S)-2-(2-methylpropyl)-4-propan-2-yl-4,5-dihydro-1,3-oxazole
• CAS: 175226-81-0
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: ZXYKEXADEPWSLI-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S)-2-异丁基-4-异丙基-4,5-二氢-1,3-恶唑 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以33%的产率得到(5S)-3,5-diisopropyl-5,6-dihydro-2H-1,4-oxazin-2-one
  参考文献：
  名称：

  Oxidative Rearrangement of 2-Substituted Oxazolines. A Novel Entry to 5,6-Dihydro-2H-1,4-oxazin-2-ones and Morpholin-2-ones

  摘要：

  A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent; (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important ''chiral glycine'' synthons for asymmetric synthesis of a-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of a-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a ''nitrilium to acylium'' 1,2-migration.

  DOI：

  10.1021/jo952144f
• 作为产物：
  描述：

  异戊酰氯 在 sodium hydroxide 、 氯化亚砜 、 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (4S)-2-异丁基-4-异丙基-4,5-二氢-1,3-恶唑
  参考文献：
  名称：

  Oxidative Rearrangement of 2-Substituted Oxazolines. A Novel Entry to 5,6-Dihydro-2H-1,4-oxazin-2-ones and Morpholin-2-ones

  摘要：

  A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent; (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important ''chiral glycine'' synthons for asymmetric synthesis of a-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of a-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a ''nitrilium to acylium'' 1,2-migration.

  DOI：

  10.1021/jo952144f

文献信息

• Benzyne-mediated trichloromethylation of chiral oxazolines
  作者：Xin Huang、Weizhao Zhao、De-Li Chen、Yaling Zhan、Tingting Zeng、Huiquan Jin、Bo Peng

  DOI：10.1039/c9cc00557a

  日期：——

  A three-component reaction between benzyne, oxazolines and chloroform was developed for the synthesis of trichloromethylated chiral oxazolidines. Benzyne not only serves as an electrophile towards oxazolines but also acts as a base for the deprotonation of chloroform. The dual functions of benzyne enable the trichloromethylation of chiral oxazolines and thus construct chiral N,O-quaternary stereocenters

  建立了苯炔，恶唑啉和氯仿之间的三组分反应，用于合成三氯甲基化的手性恶唑烷。苯并不仅充当恶唑啉的亲电子试剂，而且还充当氯仿去质子化的基础。苯并炔的双重功能使手性恶唑啉能够进行三氯甲基化，从而构建了手性N，O-四元立体中心。
• Oxidative Rearrangement of 2-Substituted Oxazolines. A Novel Entry to 5,6-Dihydro-2<i>H</i>-1,4-oxazin-2-ones and Morpholin-2-ones
  作者：Cynthia M. Shafer、Tadeusz F. Molinski

  DOI：10.1021/jo952144f

  日期：1996.1.1

  A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent; (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important ''chiral glycine'' synthons for asymmetric synthesis of a-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of a-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a ''nitrilium to acylium'' 1,2-migration.