2(S)-(1-aza-2,2-dimethyl-3-oxa-5(S)-phenylcyclopent-1-yl)-4(R)-methyl-1-oxotetrahydrofuran | 159267-69-3

• 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(S)-(1-aza-2,2-dimethyl-3-oxa-5(S)-phenylcyclopent-1-yl)-4(R)-methyl-1-oxotetrahydrofuran
• 英文别名: (3S,5R)-3-[(4S)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-3-yl]-5-methyloxolan-2-one
• CAS: 159267-69-3
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: DFIGYMIPBDMILG-KWCYVHTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2(S)-(1-aza-2,2-dimethyl-3-oxa-5(S)-phenylcyclopent-1-yl)-4(R)-methyl-1-oxotetrahydrofuran 在 lead(IV) acetate 、 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.25h， 生成 (-)-(2S,4R)-γ-hydroxynorvaline
  参考文献：
  名称：

  Synthesis of Optically Active 4-Substituted 2-Aminobutyrolactones and Homoserines by Combined Aldol/Photocyclization Reactions of Chromium Aminocarbene Complexes

  摘要：

  Aldol reactions of optically active chromium aminocarbene complexes proceeded with moderate to high diastereoselectivity. Photolysis of the aldol product gave optically active 4-substituted 2-aminobutyrolactones which could be hydrolyzed to gamma-hydroxy-alpha-amino acids. Using this procedure, (+)-bulgecenine was synthesized.

  DOI：

  10.1021/ja00101a014
• 作为产物：
  描述：

  乙醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 正丁基锂 、 air 、 一氧化碳 作用下， 生成 2(R)-(1-aza-2,2-dimethyl-3-oxa-5(S)-phenylcyclopent-1-yl)-4(S)-methyl-1-oxotetrahydrofuran 、 2(R)-(1-aza-2,2-dimethyl-3-oxa-5(S)-phenylcyclopent-1-yl)-4(R)-methyl-1-oxotetrahydrofuran 、 2(S)-(1-aza-2,2-dimethyl-3-oxa-5(S)-phenylcyclopent-1-yl)-4(R)-methyl-1-oxotetrahydrofuran
  参考文献：
  名称：

  Synthesis of Optically Active 4-Substituted 2-Aminobutyrolactones and Homoserines by Combined Aldol/Photocyclization Reactions of Chromium Aminocarbene Complexes

  摘要：

  Aldol reactions of optically active chromium aminocarbene complexes proceeded with moderate to high diastereoselectivity. Photolysis of the aldol product gave optically active 4-substituted 2-aminobutyrolactones which could be hydrolyzed to gamma-hydroxy-alpha-amino acids. Using this procedure, (+)-bulgecenine was synthesized.

  DOI：

  10.1021/ja00101a014

文献信息

• Synthesis of Optically Active 4-Substituted 2-Aminobutyrolactones and Homoserines by Combined Aldol/Photocyclization Reactions of Chromium Aminocarbene Complexes
  作者：Carsten Schmeck、Louis S. Hegedus

  DOI：10.1021/ja00101a014

  日期：1994.11

  Aldol reactions of optically active chromium aminocarbene complexes proceeded with moderate to high diastereoselectivity. Photolysis of the aldol product gave optically active 4-substituted 2-aminobutyrolactones which could be hydrolyzed to gamma-hydroxy-alpha-amino acids. Using this procedure, (+)-bulgecenine was synthesized.