(-)-(S)-3-methylhexanedioic acid | 61898-58-6

• 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: (-)-(S)-3-methylhexanedioic acid
• 英文别名: (S)-3-methylhexanedioic acid；(S)-3-methyladipic acid；(3S)-3-methylhexanedioic acid
• CAS: 61898-58-6
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: SYEOWUNSTUDKGM-YFKPBYRVSA-N

物化性质

• 沸点：
  341.4±0.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  101°C
• 溶解度：
  248 mg/mL at 26 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(S)-3-methylhexanedioic acid 在 硫酸 、 sodium 作用下， 以 甲苯 为溶剂， 反应 11.0h， 生成 ethyl (4S)-4-methyl-2-oxocyclopentane-1-carboxylate
  参考文献：
  名称：

  Synthesis and Biological Activities of (R)- and (S)-N-(4-Methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium Chloride as Potent Cytotoxic Antitubulin Agents

  摘要：

  (R,S)-1 is a potent antimitotic compound. (R)-1 center dot HCl and (S)-1 center dot HCl were synthesized from (R)- and (S)-3-methyladipic acid. Both enantiomers were potent inhibitors of cell proliferation and caused cellular microtubule loss and mitotic arrest. They inhibited purified tubulin assembly and the binding of [H-3]colchicine to tubulin, with (S)-1 being about twice as potent. Cytotoxicity against 60 tumor cell lines, however, indicated that the (S)-isomer was 10- to 88-fold more potent than the (R)-isomer.

  DOI：

  10.1021/jm2007722
• 作为产物：
  描述：

  [(S)-3-Cyclohexene-1-yl]methyl p-toluenesulphonate 生成 (-)-(S)-3-methylhexanedioic acid
  参考文献：
  名称：

  Ceder,O.; Hansson,B., Acta Chemica Scandinavica (1947), 1970, vol. 24, # 8, p. 2693 - 2698

  摘要：

  DOI：

文献信息

• Sterospecificity of pig kidney and pea seedling diamino oxidases on 2-mehtyl-1,4-diaminobutane
  作者：Enzo Santaniello、Ada Manzocchi、Pier Antonio Biondi、Camilio Secchi、Tatijana Simonic

  DOI：10.1039/c39840000803

  日期：——

  diamine oxidase from pea seedings (PDAO) oxidizes both (R)-and (S)-2-methylputrescine at the less hindered C-4, whereas pig-kindey diamine oxidase (KDAO) shows a dependence on the stereochemistry of the substrate, since the (R)-isomer is oxidized at C-1 and the (S)-isomer at the less hindered amino group at C-4.

  来自豌豆种子的二胺氧化酶（PDAO）在受阻较小的C-4处同时氧化（R）-和（S）-2-甲基酪氨酸，而猪型二胺氧化酶（KDAO）则依赖于底物的立体化学，因为（R）-异构体在C-1处被氧化，（S）-异构体在C-4处受阻较小的氨基处被氧化。
• Enantioselective Baeyer–Villiger Oxidation: Desymmetrization of Meso Cyclic Ketones and Kinetic Resolution of Racemic 2-Arylcyclohexanones
  作者：Lin Zhou、Xiaohua Liu、Jie Ji、Yuheng Zhang、Xiaolei Hu、Lili Lin、Xiaoming Feng

  DOI：10.1021/ja309262f

  日期：2012.10.17

  N'-dioxide-Sc(III) complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active ε- and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV oxidation. Enantioenriched 3-aryloxepan-2-ones, whose formation is counter to the migratory aptitude, were

  在手性 N,N'-二氧化物-Sc(III) 配合物催化剂存在下，实现了外消旋和内消旋环酮的催化对映选择性 Baeyer-Villiger (BV) 氧化。前手性环己酮和环丁酮的 BV 氧化分别提供了一系列具有光学活性的 ε- 和 γ-内酯，产率高达 99%，ee 高达 95%。同时，外消旋 2-芳基环己酮的动力学拆分也是通过异常 BV 氧化实现的。Enantioenriched 3-aryloxepan-2-ones，其形成与迁移能力相反，被优先获得。内酯和未反应的酮均具有高 ee 值。
• Synthesis of versatile chiral intermediates by enantioselective conjugate addition of alkenyl Grignard reagents to enamides deriving from (R)-(−)- or (S)-(+)-2-aminobutan-1-ol
  作者：Eric Brown、Christelle Deroye、Joël Touet

  DOI：10.1016/s0957-4166(98)00135-9

  日期：1998.5

  Conjugate addition of but-3-enylmagnesium bromide to the chiral crotonamide (R)-(+)- and (S)-(−)-3, followed by hydrolysis and oxidation, afforded enantiopure (R)-(+)- and (S)-(−)-3-methyladipic acids 8, respectively. Conjugate addition of vinylmagnesium chloride to the chiral crotonamide and cinnamamides (R)-(+)-3–5, followed by hydrolysis, gave the alkenoic acids (S)-12–14, respectively. Iodolactonization

  在手性巴豆酰胺（R）-（+）-和（S）-（-）- 3上共加入溴3-丁基溴化镁，然后水解和氧化，得到对映纯（R）-（+）-和（S）-（-）- 3-甲基己二酸8。共轭加成的乙烯基氯化镁的手性巴豆酰胺和cinnamamides（[R ）- （+） - 3 - 5，接着进行水解，得到的链烯酸（小号） - 12 - 14，分别。后者的碘内酯化导致生成5-碘甲基内酯（+）- 15 – 17，将其借助于减少Ñ -Bu 3 SNH入反式二取代的5- methyllactones（+） - 19 - 21，分别。用LiMe 2 Cu或n- Bu 2 CuLi处理碘甲基内酯（+）- 16，得到了反式-5-烷基-4-苯基内酯（-）- 22或（+）- 23。
• A Convenient Synthesis of (<i>S</i>)-3-Methyladipic Acid
  作者：James W. Leahy、Baohua Huang

  DOI：10.1080/00397919408011326

  日期：1994.11

  Abstract A rapid and facile method for the preparation of (S)-3-methyladipic acid (2) via oxidation of readily available (S)-β-citronellol is reported.

  摘要 报道了一种通过易得的 (S)-β-香茅醇氧化制备 (S)-3-甲基己二酸 (2) 的快速简便方法。
• Biotransformation of Squalene to Optically Active Methylsuccinic Acid and 3-Methyladipic Acid
  作者：Akira Tsubokura、Hisashi Yoneda、Takayuki Hirayama、Takashi Kiyota

  DOI：10.1246/cl.1992.785

  日期：1992.5

  Squalene was converted to a mixture of (R)-(+)-methylsuccinic acid and (S)-(−)-3-methyladipic acid by Saccharomycopsis lipolytica SQL349 isolated from soil. The enantiomeric excess of each compound was determined to be 99%.

  从土壤中分离出的糖脂单胞菌SQL349将角鲨烯转化为（R）-（+）-甲基琥珀酸和（S）-（-）-3-甲基己二酸的混合物。每种化合物的对映体过剩量均确定为99%。