(4S)-4-methylhexanal | 32751-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S)-4-methylhexanal
• 英文别名: (S)-4-Methylhexanal；(4S)-methylhexanal；(S)-4-methyl-hexanal；(+)(S)-3-methyl-hexanal-(6)；4-Methyl-capronaldehyd,rechtsdrehende Form；3-Methyl-hexanal-(6),rechtsdrehende Form
• CAS: 32751-95-4
• 化学式: C₇H₁₄O
• 分子量: 114.188
• InChiKey: GIGNTOMJQYNUNL-ZETCQYMHSA-N

物化性质

• 沸点：
  141.2±8.0 °C(Predicted)
• 密度：
  0.805±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4S)-4-methylhexanal 在 氢氧化钾 、 一水合肼 、 二乙二醇 作用下， 生成 S-(+)-3-甲基己烷
  参考文献：
  名称：

  Freudenberg; Lwowski, Justus Liebigs Annalen der Chemie, 1954, vol. 587, p. 220

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-3-methylpentyl p-toluenesulfonate 在 magnesium 、 lithium bromide 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 (4S)-4-methylhexanal
  参考文献：
  名称：

  Total Synthesis and Structural Elucidation of the Antifungal Agent Papulacandin D

  摘要：

  Condensation of the aryllithium reagents, prepared from the bromides 10 and 11 and tert-butyllithium, with lactone 19 and acid-catalyzed spirocyclization gave the papulacandin spiroketals 14 and 15. Subsequent protection using di-tert-butylsilyl bis(trifluoromethanesulfonate) gave the diols 31 and 30. Isoleucine (37) was converted using a double Wittig reaction sequence and propargylation of the intermediate aldehyde 46 into the alkynol 47. Separation of the C-7 epimers of 47 was achieved using kinetic resolution via Sharpless epoxidation. Both alkynol epimers 53 and 57 were converted into the papulacandin side chain esters 65 and 66 using a hydrozirconation and palladium(0)-catalyzed coupling sequence. Comparisons of Mosher ester derivatives of 65 and 66 with the Mosher ester derivative of the natural papulacandin side chain and further degradation were consistent with the stereochemistry of the natural product being 7S,14S. Esterification of the spiroketals with the mixed anhydride 70 and global deprotection gave papulacandin D (1).

  DOI：

  10.1021/jo951895e

文献信息

• L-(-)-Menthol in the Synthesis of Key Synthons for Optically Active Methyl-Branched Insect Pheromones
  作者：G. Yu. Ishmuratov、M. P. Yakovleva、V. A. Ganieva、D. V. Amirkhanov、G. A. Tolstikov

  DOI：10.1007/s10600-006-0019-4

  日期：2005.11

  A synthesis of optically active 4S-methylhexanal, 1-bromo-3S-methylheptane, and 1-bromo-3S-methylundecane, which are key synthons for several methyl-branched insect pheromones, that is based on chemically selective transformations of 6-tosyloxy- and 6-iodoisopropyl-4R-methylhexanoates that are available from L-(-)-menthol was proposed.

  提出了一种合成光学活性4S-甲基己醛、1-溴-3S-甲基庚烷和1-溴-3S-甲基十一烷的方法，这些化合物是几种甲基支链昆虫信息素的重要合成材料。该方法基于从L-(-)-薄荷醇获得的6-托苯基氧基和6-碘异丙基-4R-甲基己酸酯的化学选择性转化。
• Reexamining Povarov Reaction’s Scope and Limitation in the Generation of HCV-NS4A Peptidomimetics
  作者：Maan T. Khayat、Abdelsattar M. Omar、Mahmoud A. Elfaky、Yosra A. Muhammad、Elaf A. Felemban、Khalid M. El-Say、Moustafa E. El-Araby

  DOI：10.1155/2022/8181543

  日期：2022.2.10

  mimics that cover the region between residues Ile-25′ to Arg-28′. The synthetic plan featured the Povarov reaction as an efficient strategy to construct the 1,7-naphthyridine core. Although this reaction has been reported in many literatures, critical assessments for its scope and limitations are scarce. In our work, we found that Povarov was extremely sensitive to alkene and aldehyde reactants. Moreover

  慢性丙型肝炎是一种全球健康威胁和无声杀手。尽管在预防和治疗这种疾病方面取得了重大进展，但研究仍在继续发现新的直接抗病毒药物 (DAA)，尤其是针对新靶点的药物。我们的研究旨在利用 NS4A 结合位点开发丙型肝炎病毒 (HCV) NS3 蛋白酶的拟肽抑制剂。在以前的报告中，我们可以提供肽和非肽 /4A 抑制剂对该位点的可调性的证据。在本报告中，我们使用基于结构的技术设计 1,2,3,4-四氢-1,7-萘啶衍生物作为 NS4A 核心模拟物，覆盖残基 Ile-25' 到 Arg-28' 之间的区域。该合成计划将波瓦罗夫反应作为构建 1,7-萘啶核的有效策略。尽管许多文献都报道了这种反应，但对其范围和局限性的批判性评估却很少。在我们的工作中，我们发现波瓦罗夫对烯烃和醛反应物极为敏感。此外，使用吡啶胺不如苯胺成功。最引人注目的结果是化合物在纯化和储存过程中缺乏稳定性。在稳定性问题中幸存下来的四种化合物
• Hydroformylation of (+)(S)-3-methylpent-1-ene
  作者：P. Pino、S. Pucci、F. Piacenti、G. Dell'Amico

  DOI：10.1039/j39710001640

  日期：——

  In the hydroformylation of (+)(S)-3-methylpent-1-ene the extent of racemization of the synthesized dissymmetric aldehydes is shown to decrease with increasing pressure of carbon monoxide; the ratio of erythro- to threo-2,3-dimethylpentanal formed differs considerably from the diastereoisomeric equilibrium value.

  在（+）（S）-3-甲基戊-1-烯的加氢甲酰化反应中，合成的不对称醛的外消旋化程度随一氧化碳压力的增加而降低。所形成的赤型-苏型-2,3-二甲基戊醛的比例与非对映异构平衡值有很大差异。
• Assignment of (6R*,10R*)-relative stereochemistry to the major component of the sex pheromone of the maritime pine scale, matsucoccus feytaudi
  作者：Kenji Mori、Susumu Harashima

  DOI：10.1016/s0040-4039(00)79447-0

  日期：1991.10

  (2E,4E,6R,10S)-4,6,10-Trimethyl-2,4-dodecadien-7-one 1 and its (6S,10S)-isomer were synthesized. The H-1 NMR spectrum of (6S,10S)-1 coincided with that reported for the major component of the sex pheromone of Matsucoccus feytaudi, which must therefore be either (6S,10S)- or (6R,10R)-1.

  (2E,4E,6R,10S)-4,6,10-三甲基-2,4-十二碳二烯-7-酮 1 及其 (6S,10S)-异构体被合成。 (6S,10S)-1 的 H-1 NMR 谱与松突圆蚧 Matsucoccus feytaudi 性信息素主要成分的报告相符，因此该物质必定是 (6S,10S)-或 (6R,10R)-1。
• Highly regio-, (E)-stereo-, and diastereoselective SN2′ addition of organocuprates to chiral allylic cyclic carbonates
  作者：Suk-Ku Kang、Dong-Ha Lee、Hyeong-Su Sim、Jong-Suk Lim

  DOI：10.1016/s0040-4039(00)60065-5

  日期：1993.1

  diols with RCu(CN)Li· BF3, RCu(CN)MgBr·BF3, or RMgBr·CuI (cat) in THF at −78 °C proceeded in SN2′ fashion and resulted in the formation of alkylated (E)-allylic alcohols with remarkably high diastereoselectivity. This reaction represents an efficient 1, 3-chirality transfer method.

  无环乙烯基二醇的环状碳酸酯与RCu（CN）Li·BF 3，RCu（CN）MgBr·BF 3或RMgBr·CuI（cat）在THF中在-78°C下以S N 2'方式进行反应，导致形成具有极高非对映选择性的烷基化（E）-烯丙基醇。该反应代表一种有效的1、3手性转移方法。