(R)-(+)-3-methylundecan-1-ol | 84567-94-2

• 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: (R)-(+)-3-methylundecan-1-ol
• 英文别名: (R)-3-methyl-1-undecanol；(R)-3-methylundecan-1-ol；(R)-3-methylundecanol；(+)(R)-3-methyl-undecanol-(1)；(3R)-3-Methylundecan-1-OL
• CAS: 84567-94-2
• 化学式: C₁₂H₂₆O
• 分子量: 186.338
• InChiKey: CTVPPKBJEDDIHQ-GFCCVEGCSA-N

物化性质

• 沸点：
  245.5±8.0 °C(Predicted)
• 密度：
  0.829±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  13
• 可旋转键数：
  9
• 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：

  (R)-(+)-3-methylundecan-1-ol 在 氢溴酸 作用下， 生成 3-甲基十一烷
  参考文献：
  名称：

  Prout; Cason; Ingersoll, Journal of the American Chemical Society, 1948, vol. 70, p. 304

  摘要：

  DOI：
• 作为产物：
  描述：

  octyllithium 在 palladium on activated charcoal copper(l) iodide 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 (R)-(+)-3-methylundecan-1-ol
  参考文献：
  名称：

  The use of methyl substituted chiral synthons in the synthesis of pine sawflies pheromones

  摘要：

  DOI：

  10.1016/s0040-4020(01)89828-8

文献信息

• SYNTHESIS OF THE SEX-ATTRACTANT OF PINE SAWFLIES (DIPRION SPECIES); (2<i>S</i>,3<i>R</i>,7<i>R</i>)- AND (2<i>S</i>,3<i>R</i>,7<i>S</i>)-3,7-DIMETHYLPENTADECAN-2-OL
  作者：Tadashi Kikukawa、Motomasa Imaida、Akira Tai

  DOI：10.1246/cl.1982.1799

  日期：1982.11.5

  candidate epimers, (2S,3R,7R)-and (2S,3R,7S)-3,7-dimethylpentadecan-2-ol were synthesized by the coupling reaction of optically active C5 and C12 units. The C12 units, (R)-(−)-and (S)-(+)-1-bromo-2-methyludecane were prepared from (R)-(+)-pulegone. The C5 unit, (2R,3S)-2-methyl-3-tetrahydropyranoxy-1-tosyloxybutane was derived from (2S,3S)-2-methyl-3-hydroxybutyric acid prepared by the reported prodedure

  为了建立松叶蜂双朊病毒性引诱剂的立体化学，合成了两种候选差向异构体，(2S,3R,7R)-和(2S,3R,7S)-3,7-二甲基十五烷-2-ol光学活性 C5 和 C12 单元的偶联反应。C12 单元 (R)-(-)- 和 (S)-(+)-1-bromo-2-methyludecane 由 (R)-(+)-pulegone 制备。C5 单元 (2R,3S)-2-methyl-3-tetrahydropyranoxy-1-tosyloxybutane 衍生自 (2S,3S)-2-methyl-3-hydroxybutyric 酸，由报道的程序制备。
• Syntheses of the Sex-Attractant of Pine Sawflies
  作者：Tadashi Kikukawa、Motomasa Imaida、Akira Tai

  DOI：10.1246/bcsj.57.1954

  日期：1984.7

  In order to establish the stereochemistry of the sex attractant of various species of pine sawflies, (2S,3R,7R)-, (2S,3R,7S)- and (2S,3S,7S)-2-acetoxy- and 2-propionyloxy-3,7-dimethylpentadecane were synthesized. The alcohol moiety of each pheromone was prepared by the coupling of Grignard reagent of C12 block with tosylate of C5 block. The C12 blocks, (R)- and (S)-1-bromo-2-methylundecane, were prepared from (R)-(+)-pulegone. The C5 blocks, (2R,3S)- or (2S,3S)-2-methyl-3-tetrahydropyranyloxy-1-(tosyloxy)butane, were derived from (2S,3S)- or (2R,3S)-2-methyl-3-hydroxybutyric acid prepared by the enantio-differentiating hydrogenation of methyl 2-methyl-3-oxobutyrate over the asymmetrically modified nickle catalyst.

  为了确定不同种类松锯齿蝇性引诱剂的立体化学结构，合成了(2S,3R,7R)-、(2S,3R,7S)-和(2S,3S,7S)-2-乙酰氧基和 2-丙酰氧基-3,7-二甲基十五烷。每种信息素的醇分子都是通过 C12 嵌段的格氏试剂与 C5 嵌段的甲苯磺酸盐偶联制备的。C12 嵌段(R)-和(S)-1-溴-2-甲基十一烷是由(R)-(+)-pulegone 制备的。(2R,3S)-或(2S,3S)-2-甲基-3-四氢吡喃氧基-1-(对甲苯磺酰氧基)丁烷等 C5 嵌段是由(2S,3S)-或(2R,3S)-2-甲基-3-羟基丁酸在不对称改性镍催化剂上通过 2-甲基-3-氧代丁酸甲酯的对映异构加氢反应制备的。
• A New Protocol for the Enantioselective Synthesis of Methyl-Substituted Alkanols and Their Derivatives through a Hydroalumination/Zirconium-Catalyzed Alkylalumination Tandem Process We thank the National Science Foundation (CHE-0080795), the National Institutes of Health (GM36792), and Purdue University for support of this research. We also thank Albemarle and Boulder Chemical for assistance in the procurement of Al and Zr compounds, respectively.
  作者：Shouquan Huo、Ji-cheng Shi、Ei-ichi Negishi

  DOI：10.1002/1521-3773(20020617)41:12<2141::aid-anie2141>3.0.co;2-w

  日期：2002.6.17
• Staellberg-Stenhagen, Arkiv foer Kemi, 1949, vol. 26 A, # 12, p. 22
  作者：Staellberg-Stenhagen

  DOI：——

  日期：——
• Odinokov, V. N.; Akhmetova, V. R.; Khasanov, Kh. D., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 6.1, p. 908 - 914
  作者：Odinokov, V. N.、Akhmetova, V. R.、Khasanov, Kh. D.、Abduvakhabov, A. A.、Khalilov, L. M.、et al.

  DOI：——

  日期：——