N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1S,5R,7R)-10,10-dimethyl-3-oxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane | 137441-14-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1S,5R,7R)-10,10-dimethyl-3-oxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane
• 英文别名: (1S,5R,7R)-2-[(2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoyl]-10,10-dimethyl-4-oxa-2-azatricyclo[5.2.1.01,5]decan-3-one
• CAS: 137441-14-6；137493-23-3；137493-26-6；137493-28-8
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: VUMPHWXRNQBADB-OAFDLETRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1S,5R,7R)-10,10-dimethyl-3-oxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane 在 sodium methylate 作用下， 生成 methyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate
  参考文献：
  名称：

  A superior chiral auxiliary in aldol condensation: camphor-based oxazolidone

  摘要：

  The aldol reactions from boron enolate derived from camphor-based N-propionyloxazolidone exhibit exceptionally high stereoselection. The initial aldol adducts from lithium mediated reactions equilibrate to furnish erythro isomers. Erythro selection is controlled by the choice of the enolate counterion.

  DOI：

  10.1016/0040-4039(91)80084-j
• 作为产物：
  描述：

  (6R,7aR)-8,8-dimethylhexahydro-2H-3a,6-methanobenzo[d]-oxazol-2-one 在 甲醇 、 phosphate buffer 、 三氟甲磺酸二丁硼 、 双氧水 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 反应 8.5h， 生成 N-<(2S,3S)-3-hydroxy-2-methyl-3-phenylpropionyl>-(1S,5R,7R)-10,10-dimethyl-3-oxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane
  参考文献：
  名称：

  Asymmetric aldol reactions: a novel model for switching between chelation- and non-chelation-controlled aldol reactions

  摘要：

  A new camphor-based N-propionyloxazolidinethione provides remarkable levels of asymmetric induction for both chelation-and non-chelation-controlled aldol processes. While the aldol condensation of the derived di-n-butylboryl enolate with various aldehydes affords the 'Evans'' syn aldol with excellent diastereoselectivity, the chlorotitanium enolate gives the ''non-Evans' syn aldol expected from chelation control. Most noteworthy is the observation that the sense of facial selectivity from the chlorotitanium enolate of propionyloxazolidinethione is opposite to that obtained from propionyloxazolidinone. This important finding illustrates the importance of increased chelating potential of the enolate ligand, ring thiocarbonyl, in maximizing the aldol pi-facial discrimination. Final nondestructive chiral auxiliary removal via hydroperoxide-assisted hydrolysis and subsequent esterification provides enantiomerically pure methoxy-carbonyl aldols.

  DOI：

  10.1021/ja00060a010