N-<(2R,3R)-3-hydroxy-2-methyl-4-octenoyl>-(1S,5R,7R)-10,10-dimethyl-3-oxo-2-aza-4-oxatricyclo<6.2.1.0^1,5>decane | 175286-96-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-<(2R,3R)-3-hydroxy-2-methyl-4-octenoyl>-(1S,5R,7R)-10,10-dimethyl-3-oxo-2-aza-4-oxatricyclo<6.2.1.0^1,5>decane
• 英文别名: (1S,5R,7R)-2-[(E,2R,3R)-3-hydroxy-2-methyloct-4-enoyl]-10,10-dimethyl-4-oxa-2-azatricyclo[5.2.1.01,5]decan-3-one
• CAS: 175286-96-1
• 化学式: C₁₉H₂₉NO₄
• 分子量: 335.444
• InChiKey: JNDMPJABQIGPRH-USWPPSCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<(2R,3R)-3-hydroxy-2-methyl-4-octenoyl>-(1S,5R,7R)-10,10-dimethyl-3-oxo-2-aza-4-oxatricyclo<6.2.1.0^1,5>decane 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 (E)-(2R,3R)-3-Hydroxy-2-methyl-oct-4-enoic acid
  参考文献：
  名称：

  A General, Highly Anti-Stereoselective Aldolization Method via Camphor-Derived Boryl Enolates

  摘要：

  Camphor-derived chiral boryl enolates are highly reactive and highly anti-stereoselective enolate synthon systems in aldol addition reactions promoted by a TiCl4 or SnCl4 cocatalyst. More significantly, this high-yield reaction exhibits remarkable generality with respect to the aldehyde nature, as illustrated by the rapid and anti-stereoselective aldolizations with the simple saturated and unsaturated aliphatic aldehydes, and aromatic aldehydes at temperatures as low as -90 degrees C. The enhanced reaction generality and anti stereoselectivity of camphor-derived boryl enolates suggests the importance of the nature of chiral auxiliary architecture in determining the aldol bond construction process. Final nondestructive camphor-based auxiliary removal via hydroperoxide-mediated hydrolysis affords enantiomerically pure anti-beta-hydroxy-alpha-methyl aldol products.

  DOI：

  10.1021/jo9520147
• 作为产物：
  描述：

  (6R,7aR)-8,8-dimethylhexahydro-2H-3a,6-methanobenzo[d]-oxazol-2-one 在 三氟甲磺酸二丁硼 、 四氯化钛 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.83h， 生成 N-<(2R,3R)-3-hydroxy-2-methyl-4-octenoyl>-(1S,5R,7R)-10,10-dimethyl-3-oxo-2-aza-4-oxatricyclo<6.2.1.0^1,5>decane
  参考文献：
  名称：

  A General, Highly Anti-Stereoselective Aldolization Method via Camphor-Derived Boryl Enolates

  摘要：

  Camphor-derived chiral boryl enolates are highly reactive and highly anti-stereoselective enolate synthon systems in aldol addition reactions promoted by a TiCl4 or SnCl4 cocatalyst. More significantly, this high-yield reaction exhibits remarkable generality with respect to the aldehyde nature, as illustrated by the rapid and anti-stereoselective aldolizations with the simple saturated and unsaturated aliphatic aldehydes, and aromatic aldehydes at temperatures as low as -90 degrees C. The enhanced reaction generality and anti stereoselectivity of camphor-derived boryl enolates suggests the importance of the nature of chiral auxiliary architecture in determining the aldol bond construction process. Final nondestructive camphor-based auxiliary removal via hydroperoxide-mediated hydrolysis affords enantiomerically pure anti-beta-hydroxy-alpha-methyl aldol products.

  DOI：

  10.1021/jo9520147

文献信息

• A General, Highly Anti-Stereoselective Aldolization Method via Camphor-Derived Boryl Enolates
  作者：Ying-Chuan Wang、An-Wei Hung、Chii-Shin Chang、Tu-Hsin Yan

  DOI：10.1021/jo9520147

  日期：1996.1.1

  Camphor-derived chiral boryl enolates are highly reactive and highly anti-stereoselective enolate synthon systems in aldol addition reactions promoted by a TiCl4 or SnCl4 cocatalyst. More significantly, this high-yield reaction exhibits remarkable generality with respect to the aldehyde nature, as illustrated by the rapid and anti-stereoselective aldolizations with the simple saturated and unsaturated aliphatic aldehydes, and aromatic aldehydes at temperatures as low as -90 degrees C. The enhanced reaction generality and anti stereoselectivity of camphor-derived boryl enolates suggests the importance of the nature of chiral auxiliary architecture in determining the aldol bond construction process. Final nondestructive camphor-based auxiliary removal via hydroperoxide-mediated hydrolysis affords enantiomerically pure anti-beta-hydroxy-alpha-methyl aldol products.