(-)-(3S)-1-(1,3,3-trimethyl-2-norbornylidene)-5-penten-3-ol | 130884-89-8

• 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: (-)-(3S)-1-(1,3,3-trimethyl-2-norbornylidene)-5-penten-3-ol
• CAS: 130884-89-8
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: VEQOGTCSWXCFJT-AADWAWOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (-)-(3S)-1-(1,3,3-trimethyl-2-norbornylidene)-5-penten-3-ol 在 戴斯-马丁氧化剂 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 (3S)-<(α-methoxy-α-(trifluoromethyl)phenylacetyl)oxy>-5-(1,3,3-trimethyl-2-norbornylidene)-1-pentene
  参考文献：
  名称：

  Optically active ketones as chiral auxiliaries in the [2,3]-Wittig rearrangement

  摘要：

  The stereochemical aspects of the [2,3]-Wittig rearrangement of optically active tertiary allyl ethers derived from (+)-camphor and (-)-fenchone were investigated. The rearrangement of the (+)-camphor derivative yielded two olefin products in a 70/30 E/Z ratio. The geometry of the trisubstituted olefin produced during the rearrangement was assigned by NOE experiments. The configuration of the newly formed carbinol center of the products was established by kinetic resolution, Mosher's method, and conversion to derivatives of known absolute configuration. The absolute configuration of the carbinol center for the Z isomer was assigned to be S and that of the E isomer to be R. The (-)-fenchone derivative gave only a single Z olefin product, which was assigned the S configuration at the carbinol center.

  DOI：

  10.1021/jo00003a048
• 作为产物：
  描述：

  2-exo-vinyl-1,3,3-trimethyl-2-endo-norbornyl allyl ether 在 六甲基磷酰三胺 、 potassium tert-butylate 、 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 以74%的产率得到(-)-(3S)-1-(1,3,3-trimethyl-2-norbornylidene)-5-penten-3-ol
  参考文献：
  名称：

  Optically active ketones as chiral auxiliaries in the [2,3]-Wittig rearrangement

  摘要：

  The stereochemical aspects of the [2,3]-Wittig rearrangement of optically active tertiary allyl ethers derived from (+)-camphor and (-)-fenchone were investigated. The rearrangement of the (+)-camphor derivative yielded two olefin products in a 70/30 E/Z ratio. The geometry of the trisubstituted olefin produced during the rearrangement was assigned by NOE experiments. The configuration of the newly formed carbinol center of the products was established by kinetic resolution, Mosher's method, and conversion to derivatives of known absolute configuration. The absolute configuration of the carbinol center for the Z isomer was assigned to be S and that of the E isomer to be R. The (-)-fenchone derivative gave only a single Z olefin product, which was assigned the S configuration at the carbinol center.

  DOI：

  10.1021/jo00003a048