2(S)-(1-aza-2,2-dimethyl-3-oxa-5(R)-phenylcyclopent-1-yl)-4(S)-(1,3-dioxa-2,2,-dimethylcyclopent-5(R)-yl)-1-oxotetrahydrofuran | 159267-72-8

• 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(R)-phenylcyclopent-1-yl)-4(S)-(1,3-dioxa-2,2,-dimethylcyclopent-5(R)-yl)-1-oxotetrahydrofuran
• 英文别名: (3S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-[(4R)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-3-yl]oxolan-2-one
• CAS: 159267-72-8
• 化学式: C₂₀H₂₇NO₅
• 分子量: 361.438
• InChiKey: FGTKHGMDVLAROX-LUKYLMHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2(S)-(1-aza-2,2-dimethyl-3-oxa-5(R)-phenylcyclopent-1-yl)-4(S)-(1,3-dioxa-2,2,-dimethylcyclopent-5(R)-yl)-1-oxotetrahydrofuran 在 palladium dihydroxide 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 25.0h， 生成 (3S,5S)-3-amino-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]oxolan-2-one
  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：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 正丁基锂 、 air 、 一氧化碳 作用下， 生成 trans-2(SR)-(1-aza-2,2-dimethyl-3-oxa-5(R)-phenylcyclopent-1-yl)-4(RS)-(1,3-dioxa-2,2,-dimethylcyclopent-5(R)-yl)-1-oxotetrahydrofuran 、 2(R)-(1-aza-2,2-dimethyl-3-oxa-5(R)-phenylcyclopent-1-yl)-4(R)-(1,3-dioxa-2,2,-dimethylcyclopent-5(R)-yl)-1-oxotetrahydrofuran 、 2(S)-(1-aza-2,2-dimethyl-3-oxa-5(R)-phenylcyclopent-1-yl)-4(S)-(1,3-dioxa-2,2,-dimethylcyclopent-5(R)-yl)-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.