(3S)-undecane-1,3-diol | 115458-75-8

• 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: (3S)-undecane-1,3-diol
• CAS: 115458-75-8
• 化学式: C₁₁H₂₄O₂
• 分子量: 188.31
• InChiKey: CSFUNXXUTSRHPN-NSHDSACASA-N

物化性质

• 沸点：
  298.1±8.0 °C(Predicted)
• 密度：
  0.916±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S)-undecane-1,3-diol 在 palladium on activated charcoal lithium aluminium tetrahydride 、 dicobalt octacarbonyl 、 pyridine-SO3 complex 、 camphor-10-sulfonic acid 、 氢气 、 sodium acetate 、 二异丁基氢化铝 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 环己烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.33h， 生成 (7S)-7-methylheptadecane
  参考文献：
  名称：

  烷基支链烷烃的对映选择性合成。7，11-二甲基十七烷和7-甲基十七烷的立体异构体的合成

  摘要：

  已经合成了7，11-二甲基十七烷和7-甲基十七烷的立体异构体。使用的关键步骤是分子内氢化物从具有定义的绝对立体化学的仲γ-苄氧基转移到通过路易斯酸处理合适的叔Co（2）（CO）（6）-复杂的炔丙醇而生成的阳离子。该方法的应用提供了立体化学定义的α-烷基-γ-羟基-乙炔，所述α-烷基-γ-羟基-乙炔在氢化并进一步还原性除去羟基后产生仲烷基烃。

  DOI：

  10.1021/jo0055436
• 作为产物：
  描述：

  1,3,5-戊三醇 在 吡啶 、 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 环己烷 为溶剂， 反应 65.0h， 生成 (3S)-undecane-1,3-diol
  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

文献信息

• Resolution of 1,3-alkanediols via chiral spiroketals derived from ℓ-menthone
  作者：Toshiro Harada、Hideaki Kurokawa、Akira Oku

  DOI：10.1016/s0040-4039(00)96640-1

  日期：1987.1
• 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：——
• 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
  作者：Toshiro Harada、Hideaki Kurokawa、Yasuhiro Kagamihara、Sachi Tanaka、Atsushi Inoue、Akira Oku

  DOI：10.1021/jo00031a019

  日期：1992.2

  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.
• Enantioselective Synthesis of Alkyl-Branched Alkanes. Synthesis of the Stereoisomers of 7,11-Dimethylheptadecane and 7-Methylheptadecane, Components of the Pheromone of <i>Lambdina</i> Species
  作者：David D. Díaz、Víctor S. Martín

  DOI：10.1021/jo0055436

  日期：2000.11.1

  The stereoisomers of 7,11-dimethylheptadecane and 7-methylheptadecane have been synthesized. The key step used has been the intramolecular hydride transfer from a secondary gamma-benzyloxy group with defined absolute stereochemistry to a cation generated by Lewis acid treatment of the suitable tertiary Co(2)(CO)(6)-complexed propargylic alcohol. The application of this method provided stereochemically

  已经合成了7，11-二甲基十七烷和7-甲基十七烷的立体异构体。使用的关键步骤是分子内氢化物从具有定义的绝对立体化学的仲γ-苄氧基转移到通过路易斯酸处理合适的叔Co（2）（CO）（6）-复杂的炔丙醇而生成的阳离子。该方法的应用提供了立体化学定义的α-烷基-γ-羟基-乙炔，所述α-烷基-γ-羟基-乙炔在氢化并进一步还原性除去羟基后产生仲烷基烃。