(2R,3S,4R)-2,4-dimethylheptane-1,3-diol | 145514-06-3

• 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: (2R,3S,4R)-2,4-dimethylheptane-1,3-diol
• 英文别名: rel-(2R,3S,4R)-2,4-Dimethyl-1,3-heptanediol
• CAS: 145514-06-3
• 化学式: C₉H₂₀O₂
• 分子量: 160.257
• InChiKey: XFGZFWSLZQSDBW-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  5
• 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：

  (2R,3S,4R)-2,4-dimethylheptane-1,3-diol 在 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 (2S,3S,4R)-3-((4-methoxybenzyl)oxy)-2,4-dimethylheptanal
  参考文献：
  名称：

  氨基甲酸酯A和B的不对称合成研究

  摘要：

  开发了一种方便的方法，用于从三杂环片段和聚酮化合物6衍生出Hoiamides A（1）和B（2）的非对映选择性合成关键中间体5。主要特征是通过完善的Oppolzer的反醛醇缩合酶和Paterson的抗醛醇缩合法，从C33到C36连续构建四个Hoiamides A（1）立体异构中心。此外，不对称的烯丙基化也被用作关键步骤，以在C32形成hoiamides A（1）的立体中心。

  DOI：

  10.1016/j.tetlet.2016.11.004
• 作为产物：
  描述：

  2-甲基戊醛 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 20.83h， 生成 (2R,3S,4R)-2,4-dimethylheptane-1,3-diol
  参考文献：
  名称：

  Stereoselective total synthesis of (.+-.)-invictolide. An efficient preparation of a trisubstituted .delta.-lactone from aldol precursors

  摘要：

  The stereoselective total synthesis of (+/-)-invictolide (1), a component of the queen recognition pheromone of Solenopsis invicta, is described. The TiCl4-mediated addition of silyl ketene thioacetal 8 to (+/-)-3-(benzyloxy)-2-methylpropionaldehyde afforded exclusively thioester 10, in 65% yield, which was straightforwardly converted to diol 5 (ca. 31% yield). Diol 5 was also prepared after LiAlH4 reduction of the major aldol formed in the condensation between the lithium enolate of 2,6-di-tert-butyl-4-methylphenyl propanoate and (+/-)-2-methylvaleraldehyde (ca.50% overall yield). Intramolecular alkylation (t-BuOK-THF) of 6 or 7 gave a 40:60 mixture of (+/-)-1 and its C(3) epimer. Catalytic hydrogenation of unsaturated lactone 17 afforded (+/-)-1 in 80% yield.

  DOI：

  10.1021/jo00054a014

文献信息

• Highly Stereoselective Syntheses of All 1,2,3-<i>Me,OH,Me</i>Triads<i>via</i>Asymmetric Hydrogenation Reactions
  作者：Ye Zhu、Kevin Burgess

  DOI：10.1002/adsc.201200709

  日期：2013.1.14

  Iridium‐catalyzed asymmetric hydrogenations of chiral alkenes were used to access four pivotal α,ω‐functionalized chirons, that contain widely occurring stereochemical 1,2,3‐Me,OH,Me motifs. A chiral analogue of Crabtree’s catalyst was used in key hydrogenation steps to form these motifs with high stereochemical purities. An application of one of these chirons is illustrated here with a synthesis of

  铱催化的手性烯烃的不对称氢化反应可用于获得四个关键的α，ω-官能化的Chiron，其中包含广泛存在的立体化学1,2,3- Me，OH，Me基序。在关键的氢化步骤中使用Crabtree催化剂的手性类似物形成具有高立体化学纯度的这些基序。此处举例说明了这些chiron之一的应用，以及（-）-invictolide的合成。
• Studies toward asymmetric synthesis of hoiamides A and B
  作者：Ming Li、Pan Han、Zhuo-Ya Mao、Wen Zhou、Chang-Mei Si、Juan Xiong、Bang-Guo Wei、Jin-Feng Hu

  DOI：10.1016/j.tetlet.2016.11.004

  日期：2016.12

  for diastereoselective synthesis of the key intermediate 5 from triheterocyclic fragment and polyketide 6 for hoiamides A (1) and B (2) was developed. The main feature is the successive construction of four stereogenic centers from C33 to C36 for hoiamides A (1) through the well-established Oppolzer’s anti-aldol and Paterson’s anti-aldol methodology. Furthermore, asymmetric allylation was also utilized

  开发了一种方便的方法，用于从三杂环片段和聚酮化合物6衍生出Hoiamides A（1）和B（2）的非对映选择性合成关键中间体5。主要特征是通过完善的Oppolzer的反醛醇缩合酶和Paterson的抗醛醇缩合法，从C33到C36连续构建四个Hoiamides A（1）立体异构中心。此外，不对称的烯丙基化也被用作关键步骤，以在C32形成hoiamides A（1）的立体中心。
• Stereoselective total synthesis of (.+-.)-invictolide. An efficient preparation of a trisubstituted .delta.-lactone from aldol precursors
  作者：Ronaldo Aloise Pilli、Maria Marcia Murta

  DOI：10.1021/jo00054a014

  日期：1993.1

  The stereoselective total synthesis of (+/-)-invictolide (1), a component of the queen recognition pheromone of Solenopsis invicta, is described. The TiCl4-mediated addition of silyl ketene thioacetal 8 to (+/-)-3-(benzyloxy)-2-methylpropionaldehyde afforded exclusively thioester 10, in 65% yield, which was straightforwardly converted to diol 5 (ca. 31% yield). Diol 5 was also prepared after LiAlH4 reduction of the major aldol formed in the condensation between the lithium enolate of 2,6-di-tert-butyl-4-methylphenyl propanoate and (+/-)-2-methylvaleraldehyde (ca.50% overall yield). Intramolecular alkylation (t-BuOK-THF) of 6 or 7 gave a 40:60 mixture of (+/-)-1 and its C(3) epimer. Catalytic hydrogenation of unsaturated lactone 17 afforded (+/-)-1 in 80% yield.