(2S,4S)-2,4-dimethyl-1-octanol | 249745-91-3

• 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: (2S,4S)-2,4-dimethyl-1-octanol
• 英文别名: (2S,4S)-2,4-dimethyloctan-1-ol；(2S,4S)-dimethyloctan-1-ol
• CAS: 249745-91-3
• 化学式: C₁₀H₂₂O
• 分子量: 158.284
• InChiKey: DGPIFVIIBUMGDJ-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  6
• 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

• 作为反应物：
  描述：

  (2S,4S)-2,4-dimethyl-1-octanol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(2S,4S)-2,4-dimethyl-1-iodo-octane
  参考文献：
  名称：

  通过Zr催化的烯烃不对称碳铝烷基化（ZACA反应）高效且选择性地合成（S，R，R，S，R，S）-4,6,8,10,16,18-六甲基二十二烷。

  摘要：

  （S，R，R，S，R，S）-4,6,8,10,16,18-六甲基甲基二十二烷（1）以11％的产率按最长线性顺序从11％合成，大于或等于98％纯的（S）-β-香茅醛和6个额外的步骤，以11％的产率从丙烯制备11个。六个不对称碳中心中的五个是通过ZACA反应（5次），一种脂肪酶催化的乙酰化反应和两次色谱操作催化和立体选择性生成的。

  DOI：

  10.1021/ol703056u
• 作为产物：
  描述：

  (2R,4S)-5-((tert-butyldiphenylsilyl)oxy)-2,4-dimethylpentan-1-ol 在 palladium on activated charcoal 、 草酰氯 、 四丁基氟化铵 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2S,4S)-2,4-dimethyl-1-octanol
  参考文献：
  名称：

  Synthesis of (S,R,R,S,R,S)-4,6,8,10,16,18- Hexamethyldocosane from Antitrogus parvulus via Diastereoselective Hydrogenations

  摘要：

  The hydrocarbon 1 was prepared via a series of catalyst-controlled diastereoselective hydrogenations beginning with fragments derived from the Roche ester.

  DOI：

  10.1021/ol070298z

文献信息

• Iterative Deoxypropionate Synthesis Based on a Copper-Mediated Directed Allylic Substitution: Formal Total Synthesis of Borrelidin (C3–C11 Fragment)
  作者：Christian Herber、Bernhard Breit

  DOI：10.1002/chem.200600343

  日期：2006.8.25

  alkylation strategies such as enolate reactivity as well as costs and problems associated with the chiral auxiliary. Practicability of this new method is demonstrated through application in natural product syntheses. Thus, an efficient synthesis of the northern part of the angiogenesis inhibitor borrelidin (28), the deoxypropionate building block 27, could be devised, representing a formal total synthesis

  提出了一种灵活制备任何低聚脱氧丙酸酯立体异构体的新的迭代策略，该策略依赖于对映体纯的格氏试剂的邻-DPPB-定向的铜介导的烯丙基取代。该反应在反应选择性的所有方面都得到了完美的控制。与已建立的烯醇盐烷基化方法相比，这一关键的CC键形成步骤具有相反的极性。因此，它避免了烯醇盐烷基化策略的现有问题，例如烯醇盐反应性以及与手性助剂相关的成本和问题。通过在天然产物合成中的应用证明了这种新方法的实用性。因此，可以设计出一种有效的血管生成抑制剂硼瑞林（28）北部的合成方法，即脱氧丙酸酯结构单元27，
• Pheromones of Pine Sawflies: Synthesis of a Pure (2S,3R)-3-Methylalkan-2-ol Stereoisomer via an Asymmetric 1,3-Dipolar Cycloaddition; Preparation of a Pheromone Component of Macrodiprion nemoralis
  作者：Staffan Karlsson、Hans-Erik Högberg

  DOI：10.1055/s-2000-8221

  日期：——

  paper presents a new approach to the preparation of enantiomerically pure (2S,3R)-3-methylalkan-2-ols, the esters of which are sex pheromones of several pine sawflies. Thus, an asymmetric 1,3-dipolar cycloaddition between a sulfur containing 1,3-dipole and a dipolarophile attached to (1R)-camphorsultam containing a vinyl ether functionality furnished a 90 : 10 diastereomeric mixture of trans-3,4-disubstituted

  本文提出了一种制备对映体纯 (2S,3R)-3-methylalkan-2-ols 的新方法，其酯类是几种松叶蜂的性信息素。因此，含硫的 1,3-偶极子和连接到含有乙烯基醚官能团的 (1R)-樟脑磺胺的亲偶极试剂之间的不对称 1,3-偶极环加成反应提供了 90:10 的反式 3,4-二取代四氢噻吩的非对映异构体混合物酰胺。主要的转化为对映体纯的四氢噻吩基甲基溴，其与单烷基化二噻烷单元偶联。经雷尼镍还原(2S,3R,7R,9S)-3,7,9-trimethyltridecan-2-ol，其乙酸酯即为Macrodiprion nemoralis的引诱性信息素成分。
• Sex Pheromone of the Pine Sawfly, Macrodiprion nemoralis. Stereoselective Synthesis of the Sixteen Stereoisomers of 3,7,9-Trimethyl-2-tridecyl Acetate.
  作者：Staffan Karlsson、Erik Hedenström、Luis Lezama、María I. Arriortua、Margareta Björkman、Benita H. Forngren、Tobias Forngren、Per Hartvig、Karin Markides、Ulrika Yngve、Mattias Ögren

  DOI：10.3891/acta.chem.scand.53-0620

  日期：——

  The sixteen stereoisomers of 3,7,9-trimethyl-2-tridecyl acetate (5Ac) were prepared individually, each in over 99.5% stereochemical purity. The syntheses were based on the ring opening of a pure enantiomer of cis-3,4-dimethyl-gamma-butyrolactone using a pure stereoisomer of 1-lithio-2,4-dimethyloctane, the two stereogenic centres of which were introduced with high selectivity by alkylations of the amide enolates from the appropriate enantiomers of pseudoephedrine. (2S,3R,7R,9S)-3,7,9-Trimethyl-2-tridecyl acetate (SRRS-5Ac) has recently been found to be the major component of the female sex pheromone of Macrodiprion nemoralis (Hymenoptera: Diprionidae). A synthetic method for the preparation of a sixteen isomer mixture of 5Ac is also presented. This mixture has been found to be biologically active in field tests.
• Efficient and Selective Synthesis of (<i>S</i>,<i>R</i>,<i>R</i>,<i>S</i>,<i>R</i>,<i>S</i>)-4,6,8,10,16,18-Hexamethyl- docosane via Zr-Catalyzed Asymmetric Carboalumination of Alkenes (ZACA Reaction)
  作者：Gangguo Zhu、Bo Liang、Ei-ichi Negishi

  DOI：10.1021/ol703056u

  日期：2008.3.1

  (S,R,R,S,R,S)-4,6,8,10,16,18-Hexamethyldocosane (1) was synthesized in 11% yield in 11 steps in the longest linear sequence from > or =98% pure (S)-beta-citronellal and 6 additional steps for the preparation of 11 in 23% yield from propene. Five of the six asymmetric carbon centers were generated catalytically and stereoselectively by the ZACA reaction (5 times), one lipase-catalyzed acetylation, and

  （S，R，R，S，R，S）-4,6,8,10,16,18-六甲基甲基二十二烷（1）以11％的产率按最长线性顺序从11％合成，大于或等于98％纯的（S）-β-香茅醛和6个额外的步骤，以11％的产率从丙烯制备11个。六个不对称碳中心中的五个是通过ZACA反应（5次），一种脂肪酶催化的乙酰化反应和两次色谱操作催化和立体选择性生成的。
• Synthesis of (<i>S,R,R,S,R,S</i>)-4,6,8,10,16,18- Hexamethyldocosane from <i>Antitrogus </i><i>parvulus</i> via Diastereoselective Hydrogenations
  作者：Jianguang Zhou、Ye Zhu、Kevin Burgess

  DOI：10.1021/ol070298z

  日期：2007.3.1

  The hydrocarbon 1 was prepared via a series of catalyst-controlled diastereoselective hydrogenations beginning with fragments derived from the Roche ester.