tert-butyl N-[(2S,3S)-3,4-dihydroxy-2,4-diphenylbutyl]carbamate | 924311-31-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: tert-butyl N-[(2S,3S)-3,4-dihydroxy-2,4-diphenylbutyl]carbamate
• CAS: 924311-31-9
• 化学式: C₂₁H₂₇NO₄
• 分子量: 357.45
• InChiKey: JARATZXYHBJWSJ-KGNCLDLBSA-N

物化性质

• 熔点：
  50-52 °C
• 沸点：
  543.6±50.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S,3S)-3,4-dihydroxy-2,4-diphenylbutyl]carbamate 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 以71%的产率得到Boc-(s)-3-氨基-2-苯丙酸
  参考文献：
  名称：

  A Heterodinuclear Asymmetric Catalyst for Conjugate Additions of α-Hydroxyketones to β-Substituted Nitroalkenes

  摘要：

  The bis- ProPhenol ligand was designed to facilitate formation of hetereodinuclear complexes based upon the large difference in p K a of the one phenolic OH group to the tertiary OH groups. In exploring the first example of hydroxyacetophenones as donors in asymmetric Michael reactions with nitroalkene acceptors, the best stereocontrol was observed with a zinc/ magnesium dinuclear complex where enantiomeric excesses ranged up to 92% for the major anti diastereomer.

  DOI：

  10.1021/ol062485n
• 作为产物：
  描述：

  2-羟基苯乙酮 在 chiral proline-derived zinc lithium aluminium tetrahydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 44.0h， 生成 tert-butyl N-[(2S,3S)-3,4-dihydroxy-2,4-diphenylbutyl]carbamate
  参考文献：
  名称：

  A Heterodinuclear Asymmetric Catalyst for Conjugate Additions of α-Hydroxyketones to β-Substituted Nitroalkenes

  摘要：

  The bis- ProPhenol ligand was designed to facilitate formation of hetereodinuclear complexes based upon the large difference in p K a of the one phenolic OH group to the tertiary OH groups. In exploring the first example of hydroxyacetophenones as donors in asymmetric Michael reactions with nitroalkene acceptors, the best stereocontrol was observed with a zinc/ magnesium dinuclear complex where enantiomeric excesses ranged up to 92% for the major anti diastereomer.

  DOI：

  10.1021/ol062485n

文献信息

• A Heterodinuclear Asymmetric Catalyst for Conjugate Additions of α-Hydroxyketones to β-Substituted Nitroalkenes
  作者：Barry M. Trost、Soleiman Hisaindee

  DOI：10.1021/ol062485n

  日期：2006.12.1

  The bis- ProPhenol ligand was designed to facilitate formation of hetereodinuclear complexes based upon the large difference in p K a of the one phenolic OH group to the tertiary OH groups. In exploring the first example of hydroxyacetophenones as donors in asymmetric Michael reactions with nitroalkene acceptors, the best stereocontrol was observed with a zinc/ magnesium dinuclear complex where enantiomeric excesses ranged up to 92% for the major anti diastereomer.