(2R,3R)-1-[(2S,3S)-2,3-bis(phenylmethoxymethyl)aziridin-1-yl]-3-hydroxy-2-methyl-3-phenylpropan-1-one | 134964-78-6

• 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: (2R,3R)-1-[(2S,3S)-2,3-bis(phenylmethoxymethyl)aziridin-1-yl]-3-hydroxy-2-methyl-3-phenylpropan-1-one
• CAS: 134964-78-6
• 化学式: C₂₈H₃₁NO₄
• 分子量: 445.558
• InChiKey: TWGSETYGZRFCIV-HHPVDLARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  33.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  58.77
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1-[(2S,3S)-2,3-bis(phenylmethoxymethyl)aziridin-1-yl]-3-hydroxy-2-methyl-3-phenylpropan-1-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 120.0h， 以72%的产率得到(2R,3R)-(+)-3-hydroxy-2-methyl-3-phenylpropanoic acid
  参考文献：
  名称：

  On the use of C2-symmetric aziridines as chiral auxiliaries

  摘要：

  A systematic study has been made of the utility of readily available C-2-symmetric aziridines as auxiliaries for asymmetric alkylation and aldol reactions of amide enolates. Aziridines with suitably placed oxygen atoms in the side chains proved to be useful for alkylation reactions (d.e. values up to >98%) and the results are explained in terms of an intramolecularly chelated Z-enolate species, which could be observed directly by means of NMR spectroscopy. In contrast, aziridine auxiliaries lacking side-chain oxygens performed better in aldol reactions (syn selectivity up to 98% d.e.) for which a Zimmerman-Traxler transition state is proposed. After reaction, the auxiliaries can be cleaved off nondestructively under mild conditions to afford either optically pure aldehydes or carboxylic acids.

  DOI：

  10.1016/s0040-4020(01)85546-0
• 作为产物：
  描述：

  Methanesulfonic acid (1R,2R)-2-azido-3-benzyloxy-1-benzyloxymethyl-propyl ester 在 4-二甲氨基吡啶 lithium aluminium tetrahydride 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R,3R)-1-[(2S,3S)-2,3-bis(phenylmethoxymethyl)aziridin-1-yl]-3-hydroxy-2-methyl-3-phenylpropan-1-one
  参考文献：
  名称：

  On the use of C2-symmetric aziridines as chiral auxiliaries

  摘要：

  A systematic study has been made of the utility of readily available C-2-symmetric aziridines as auxiliaries for asymmetric alkylation and aldol reactions of amide enolates. Aziridines with suitably placed oxygen atoms in the side chains proved to be useful for alkylation reactions (d.e. values up to >98%) and the results are explained in terms of an intramolecularly chelated Z-enolate species, which could be observed directly by means of NMR spectroscopy. In contrast, aziridine auxiliaries lacking side-chain oxygens performed better in aldol reactions (syn selectivity up to 98% d.e.) for which a Zimmerman-Traxler transition state is proposed. After reaction, the auxiliaries can be cleaved off nondestructively under mild conditions to afford either optically pure aldehydes or carboxylic acids.

  DOI：

  10.1016/s0040-4020(01)85546-0

文献信息

• C2-symmetric aziridines as efficient chiral auxiliaries
  作者：David Tanner、Carin Birgersson

  DOI：10.1016/s0040-4039(00)74374-7

  日期：1991.11

  The C2-symmetric aziridines 1 and 1' (available from (+)- and (-)-tartaric acid, respectively) are excellent chiral auxiliaries for asymmetric alkylation and aldol reactions.
• Tanner David, Birgersson Carin, Gogoll Adolf, Luthman Kristina, Tetrahedron, 50 (1994) N 32, S 9797-9824
  作者：Tanner David, Birgersson Carin, Gogoll Adolf, Luthman Kristina

  DOI：——

  日期：——