(4S,6R,8R,11S)-4,8-dimethyl-11-propan-2-yl-1,5-dioxaspiro[5.5]undecane | 115346-76-4

• 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: (4S,6R,8R,11S)-4,8-dimethyl-11-propan-2-yl-1,5-dioxaspiro[5.5]undecane
• CAS: 115346-76-4
• 化学式: C₁₄H₂₆O₂
• 分子量: 226.359
• InChiKey: PCDVDAKHRSIXMG-ZOBORPQBSA-N

物化性质

• 沸点：
  244.1±8.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4S,6R,8R,11S)-4,8-dimethyl-11-propan-2-yl-1,5-dioxaspiro[5.5]undecane 在 盐酸 作用下， 以 甲醇 为溶剂， 以68%的产率得到(S)-(+)-1,3-丁二醇
  参考文献：
  名称：

  Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols

  摘要：

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.

  DOI：

  10.1021/jo00031a019
• 作为产物：
  描述：

  (-)-薄荷酮 、 1,3-bis(trimethylsilanoxy)butane 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 (4S,6R,8R,11S)-4,8-dimethyl-11-propan-2-yl-1,5-dioxaspiro[5.5]undecane 、 (4R,6S,8R,11S)-4,8-dimethyl-11-propan-2-yl-1,5-dioxaspiro[5.5]undecane
  参考文献：
  名称：

  Resolution of 1,3-alkanediols via chiral spiroketals derived from ℓ-menthone

  摘要：

  DOI：

  10.1016/s0040-4039(00)96640-1

文献信息

• An enantiodifferentiating conversion of racemic 1,3-alkanediols into enantiomerically pure materials
  作者：Toshiro Harada、Hideaki Kurokawa、Akira Oku

  DOI：10.1016/s0040-4039(00)96641-3

  日期：1987.1

  Titanium tetrachloride promoted ring-cleavage reaction of a mixture of diastereomeric spiroketals derived from racemic 1,3-alkanediols and ℓ-menthone, followed by benzoylation by Mitsunobu reaction, and the subsequent hydrolysis gave enantiomerically pure 1,3-alkanediols.

  四氯化钛促进了由外消旋1，3-链烷二醇和β-薄荷酮衍生的非对映异构螺环混合物的开环反应，随后通过Mitsunobu反应进行苯甲酰化，随后水解得到对映体纯的1,3-链烷二醇。
• HARADA, TOSHIRO;KUROKAWA, HIDEAKI;OKU, AKIRA, TETRAHEDRON LETT., 28,(1987) N 41, 4843-4846
  作者：HARADA, TOSHIRO、KUROKAWA, HIDEAKI、OKU, AKIRA

  DOI：——

  日期：——