(S)-2-Methyl-3-heptanol | 66283-22-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-Methyl-3-heptanol
• 英文别名: 3-Heptanol, 2-methyl-, (S)-；(3S)-2-methylheptan-3-ol
• CAS: 66283-22-5
• 化学式: C₈H₁₈O
• 分子量: 130.23
• InChiKey: QGVFLDUEHSIZIG-QMMMGPOBSA-N

物化性质

• 沸点：
  167.2±0.0 °C(Predicted)
• 密度：
  0.819±0.06 g/cm3(Predicted)
• 溶解度：
  0.02 M

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  di-n-butylzinc 、 异戊醛 在 R,S-1,2-disubstituted ferrocenyl amino alcohol 8o 作用下， 以 正己烷 为溶剂， 反应 5.0h， 以66%的产率得到(S)-2-Methyl-3-heptanol
  参考文献：
  名称：

  Chiral auxiliaries for asymmetric synthesis: enantioselective addition of dialkylzincs to aldehydes catalyzed by chiral 1,2-disubstituted ferrocenyl amino alcohols

  摘要：

  Chiral 1,2-disubstituted ferrocenyl amino alcohols derived from (R)- and (S)-N,N-dimethyl-1-ferrocenyl-ethylamines 1 and 9 catalyze the enantioselective addition of dialkylzincs to aldehydes to afford optically active S and R secondary alcohols. The degree of enantioselectivity increases with increased bulk of substituents near the C-O and C-N bonds of the catalyst. Catalysts with R chirality at the carbon bearing the amino group and planar S chirality at the ferrocene nucleus afford S alcohols, regardless of the chirality of the carbon bearing the hydroxy group. Catalyst 8o is the most effective in ethylating benzaldehyde, and it alkylates aromatic and highly branched aliphatic aldehydes in greater-than-or-equal-to 90% ee. Only moderate selectivities are obtained in the ethylation of aliphatic aldehydes without an alpha substituent.

  DOI：

  10.1021/jo00006a048

文献信息

• Asymmetric synthesis based on chiral diamines having pyrrolidine ring
  作者：Teruaki Mukaiyama

  DOI：10.1016/s0040-4020(01)93286-7

  日期：——

  Various highly stereoselective asymmetric reactions based on chiral diamines having pyrrolidine ring are described. Some of these reactions have been successfully applied to the syntheses of natural products.

  描述了基于具有吡咯烷环的手性二胺的各种高度立体选择性的不对称反应。这些反应中的一些已经成功地应用于天然产物的合成。
• Enantioselective butylation of aliphatic aldehydes by mixed chiral lithium amide/n-BuLi dimers
  作者：Per I Arvidsson、Öjvind Davidsson、Göran Hilmersson

  DOI：10.1016/s0957-4166(99)00033-6

  日期：1999.2

  The enantioselective butylation of aliphatic aldehydes with mixtures of n-butyllithium and chiral lithium amides in a diethyl ether-dimethoxymethane solvent mixture is described. Enantiomeric excesses ranging from 91 to 98.5% were observed for several aliphatic alcohols. The asymmetric butylation of the prochiral aldehydes proceeds much faster by the mixed lithium amide/n-BuLi complexes than by tetrameric n-BuLi. (C) 1999 Elsevier Science Ltd. All rights reserved.
• WATANABE, MAKOTO;ARAKI, SHUKI;BUTSUGAN, YASUO;UEMURA, MASARU, J. ORG. CHEM., 56,(1991) N, C. 2218-2224
  作者：WATANABE, MAKOTO、ARAKI, SHUKI、BUTSUGAN, YASUO、UEMURA, MASARU

  DOI：——

  日期：——
• MUKAIYAMA, TERUAKI, TETRAHEDRON, 1981, 37, N 23, 4111-4119
  作者：MUKAIYAMA, TERUAKI

  DOI：——

  日期：——
• Chiral auxiliaries for asymmetric synthesis: enantioselective addition of dialkylzincs to aldehydes catalyzed by chiral 1,2-disubstituted ferrocenyl amino alcohols
  作者：Makoto Watanabe、Shuki Araki、Yasuo Butsugan、Masaru Uemura

  DOI：10.1021/jo00006a048

  日期：1991.3

  Chiral 1,2-disubstituted ferrocenyl amino alcohols derived from (R)- and (S)-N,N-dimethyl-1-ferrocenyl-ethylamines 1 and 9 catalyze the enantioselective addition of dialkylzincs to aldehydes to afford optically active S and R secondary alcohols. The degree of enantioselectivity increases with increased bulk of substituents near the C-O and C-N bonds of the catalyst. Catalysts with R chirality at the carbon bearing the amino group and planar S chirality at the ferrocene nucleus afford S alcohols, regardless of the chirality of the carbon bearing the hydroxy group. Catalyst 8o is the most effective in ethylating benzaldehyde, and it alkylates aromatic and highly branched aliphatic aldehydes in greater-than-or-equal-to 90% ee. Only moderate selectivities are obtained in the ethylation of aliphatic aldehydes without an alpha substituent.