(1E,5E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-{(4S,5S)-5-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-1,5-dien-3-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1E,5E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-{(4S,5S)-5-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-1,5-dien-3-one
• 英文别名: (1E,4R,5E)-4-[tert-butyl(dimethyl)silyl]oxy-1-[(4S,5S)-5-[(E)-3-[tert-butyl(dimethyl)silyl]oxyprop-1-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl]hepta-1,5-dien-3-one
• 化学式: C₂₇H₅₀O₅Si₂
• 分子量: 510.862
• InChiKey: FMLBTKOXTYTLAF-FTNMXZGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.18
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1E,5E)-4-(tert-Butyl-dimethyl-silanyloxy)-1-{(4S,5S)-5-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-1,5-dien-3-ol 在 戴斯-马丁氧化剂 作用下， 生成 (1E,5E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-{(4S,5S)-5-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-1,5-dien-3-one 、 (1E,5E)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-{(4S,5S)-5-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hepta-1,5-dien-3-one
  参考文献：
  名称：

  Remote Conformational Bias Effects on Diastereofacial Selectivity in SE2' Additions of .gamma.-Oxygenated Allylic Stannanes to Chiral Enals

  摘要：

  The enal 10 derived from (R,R)-diethyl tartrate shows matched/mismatched characteristics in BF3-promoted additions of the chiral gamma-oxygenated allylic stannanes S1, S2, R1, and R2. Both S2 and S1 afford a single syn adduct 11 and 14 with enal 10, whereas R2 and R1 give mixtures of syn and anti products 12/13 and 15/16. Racemic stannane RS2 affords a 82:18 mixture of syn adducts 11 and 12; RS1 gives the two syn adducts 14 and 15 as a 77:23 mixture. The observed facial bias in these additions is attributed to conformational effects engendered by the vicinal syn OTBS substituents which cause enal 10 to adopt a chair-like conformation. The matched additions proceed by attack on the ''outside'' face of the carbonyl grouping in the s-cis orientation of this chair-like arrangement.

  DOI：

  10.1021/jo00104a047