5-(tert-butyldiphenylsilanyloxy)-4-dibenzylaminopent-2-enoic acid methyl ester | 927682-95-9

• 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: 5-(tert-butyldiphenylsilanyloxy)-4-dibenzylaminopent-2-enoic acid methyl ester
• 英文别名: methyl (E,4R)-5-[tert-butyl(diphenyl)silyl]oxy-4-(dibenzylamino)pent-2-enoate
• CAS: 927682-95-9
• 化学式: C₃₆H₄₁NO₃Si
• 分子量: 563.812
• InChiKey: DXOFXTMHAVHONB-PDXOFIEYSA-N

物化性质

• 沸点：
  615.2±55.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(tert-butyldiphenylsilanyloxy)-4-dibenzylaminopent-2-enoic acid methyl ester 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 、 sodium methylate 、 magnesium 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 41.67h， 生成 (4R,5R)-5-(hydroxymethyl)-4-phenylpyrrolidin-2-one
  参考文献：
  名称：

  A solution to the stereochemical problems posed by amaryllidaceae constituents using a highly syn-selective arylcuprate conjugate addition to γ-amino and γ-carbamato-α,β-enoates

  摘要：

  Various substituted arylcuprates undergo stereocontrolled additions to L-serine-derived gamma-amino- and gamma-carbamato-alpha,beta-enoates with high syn-selectivities. The stereochemical outcome of these reactions is fully consistent with the reductive elimination-based model proposed previously. This method is well suited for the preparation of a broad range of biologically active amaryllidaceae constituents and their aromatic analogues. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.029
• 作为产物：
  描述：

  3-(tert-butyldiphenylsilanyloxy)-2-dibenzylamino-1-propanol 、 甲氧羰基亚甲基三苯基正膦 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.33h， 以90.6%的产率得到5-(tert-butyldiphenylsilanyloxy)-4-dibenzylaminopent-2-enoic acid methyl ester
  参考文献：
  名称：

  A solution to the stereochemical problems posed by amaryllidaceae constituents using a highly syn-selective arylcuprate conjugate addition to γ-amino and γ-carbamato-α,β-enoates

  摘要：

  Various substituted arylcuprates undergo stereocontrolled additions to L-serine-derived gamma-amino- and gamma-carbamato-alpha,beta-enoates with high syn-selectivities. The stereochemical outcome of these reactions is fully consistent with the reductive elimination-based model proposed previously. This method is well suited for the preparation of a broad range of biologically active amaryllidaceae constituents and their aromatic analogues. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.029