2(R)-(N,N-dibenzylamino)-4(R)-(1,3-dioxa-2,2,-dimethylcyclopent-5(R)-yl)-1-oxotetrahydrofuran | 159267-71-7

• 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: 2(R)-(N,N-dibenzylamino)-4(R)-(1,3-dioxa-2,2,-dimethylcyclopent-5(R)-yl)-1-oxotetrahydrofuran
• 英文别名: (3R,5R)-3-(dibenzylamino)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]oxolan-2-one
• CAS: 159267-71-7
• 化学式: C₂₃H₂₇NO₄
• 分子量: 381.472
• InChiKey: LEOBENOJIRMTNQ-NJDAHSKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2(R)-(N,N-dibenzylamino)-4(R)-(1,3-dioxa-2,2,-dimethylcyclopent-5(R)-yl)-1-oxotetrahydrofuran 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 以96%的产率得到(3R,5R)-3-Dibenzylamino-5-((R)-1,2-dihydroxy-ethyl)-dihydro-furan-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 2(R)-(N,N-dibenzylamino)-4(R)-(1,3-dioxa-2,2,-dimethylcyclopent-5(R)-yl)-1-oxotetrahydrofuran 、 2(S)-(N,N-dibenzylamino)-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