(2S,2'S)-N,N'-((6S,8S)-2,2,3,3,11,11,12,12-octamethyl-4,10-dioxa-3,11-disilatridecane-6,8-diyl)bis(2-methylbutanamide) | 1446442-22-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,2'S)-N,N'-((6S,8S)-2,2,3,3,11,11,12,12-octamethyl-4,10-dioxa-3,11-disilatridecane-6,8-diyl)bis(2-methylbutanamide)
• CAS: 1446442-22-3
• 化学式: C₂₇H₅₈N₂O₄Si₂
• 分子量: 530.94
• InChiKey: GRBFVDRDKRNNOC-MLCQCVOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  35.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,2'S)-N,N'-((6S,8S)-2,2,3,3,11,11,12,12-octamethyl-4,10-dioxa-3,11-disilatridecane-6,8-diyl)bis(2-methylbutanamide) 在 对甲基苯磺酰氟 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以55%的产率得到(4S)-2-[(2S)-butan-2-yl]-4-[[(4S)-2-[(2S)-butan-2-yl]-4,5-dihydro-1,3-oxazol-4-yl]methyl]-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  AraBOX and XyliBOX based catalysts for cyclopropanations, Diels Alder cycloadditions and allylic additions

  摘要：

  The syntheses of three novel chiral 4,4'BOX ligands are described. The three ligands each have a chiral backbone and chiral sidearms, two of which are diastereomeric. These new ligands have been applied as copper complexes to asymmetric cyclopropanation reaction of styrene with ethyldiazoacetate. Enantioselectivities of up to 70% were obtained, which is the highest ee reported from the use of this ligand class in this reaction to date. The multiple stereogenic centres in the ligand resulted in a substantial additive effect and this is discussed along with interpretation of the results for previously described 4,4'BOX ligands, and a major computational study of the multiple reaction channels involved with ligands of this type. The use of complexes of 4,4'BOX ligands, as catalysts, in an allylic alkylation is also reported for the first time and ee's of >70% have been achieved in this reaction. These ligands were also applied to a Diels-Alder test reaction and again outperformed previous examples of this ligand type. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.020
• 作为产物：
  描述：

  (S)-(+)-2-甲基丁酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 (2S,2'S)-N,N'-((6S,8S)-2,2,3,3,11,11,12,12-octamethyl-4,10-dioxa-3,11-disilatridecane-6,8-diyl)bis(2-methylbutanamide)
  参考文献：
  名称：

  AraBOX and XyliBOX based catalysts for cyclopropanations, Diels Alder cycloadditions and allylic additions

  摘要：

  The syntheses of three novel chiral 4,4'BOX ligands are described. The three ligands each have a chiral backbone and chiral sidearms, two of which are diastereomeric. These new ligands have been applied as copper complexes to asymmetric cyclopropanation reaction of styrene with ethyldiazoacetate. Enantioselectivities of up to 70% were obtained, which is the highest ee reported from the use of this ligand class in this reaction to date. The multiple stereogenic centres in the ligand resulted in a substantial additive effect and this is discussed along with interpretation of the results for previously described 4,4'BOX ligands, and a major computational study of the multiple reaction channels involved with ligands of this type. The use of complexes of 4,4'BOX ligands, as catalysts, in an allylic alkylation is also reported for the first time and ee's of >70% have been achieved in this reaction. These ligands were also applied to a Diels-Alder test reaction and again outperformed previous examples of this ligand type. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.020