(2S,4S,6S)-2,4,6-trimethylnonan-1-ol | 156197-56-7

• 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,6S)-2,4,6-trimethylnonan-1-ol
• 英文别名: (2S,4S,6S)-2,4,6-trimethyl-1-nonanol
• CAS: 156197-56-7
• 化学式: C₁₂H₂₆O
• 分子量: 186.338
• InChiKey: KBNJXYZUBZXXHR-SRVKXCTJSA-N

物化性质

• 沸点：
  232.9±8.0 °C(Predicted)
• 密度：
  0.827±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  13
• 可旋转键数：
  7
• 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,6S)-2,4,6-trimethylnonan-1-ol 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 0.5h， 生成 (4S,6S,8S,E)-ethyl 2,4,6,8-tetramethyl undec-2-enoate
  参考文献：
  名称：

  虹吸烯醛和虹吸烯酮的立体选择性合成

  摘要：

  船用聚丙烯酸酯天然产物siphonarienal和siphonarienoneone的不对称全合成已从常见的前体3中获得。该合成的关键转变是非对映选择性氧化动力学拆分，Wittig烯烃化，Grignard反应和Evans不对称烷基化，用于从可商购的原材料中安装靶分子的第三个立体异构中心。

  DOI：

  10.1016/j.tetasy.2015.07.001
• 作为产物：
  描述：

  (2S,4S,3R,5R,6S)-3,5-dihydroxy-N-methoxy-N,2,4,6-tetramethylnonanamide 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 (2S,4S,6S)-2,4,6-trimethylnonan-1-ol
  参考文献：
  名称：

  Catalytic, Asymmetric Synthesis of Siphonarienal

  摘要：

  This paper describes the synthesis of the marine natural product, siphonarienal. The key step of this synthesis is an aldol reaction that constructs most of the skeleton and sets all three stereocenters of the target in one step from commercially available starting materials. Deoxygenation and chain homologation steps complete the synthesis.

  DOI：

  10.1021/jo0160367

文献信息

• Divergent Enantioselective Total Synthesis of Siphonarienal, Siphonarienone, and Pectinatone
  作者：Jhillu Singh Yadav、D. Narasimha Chary、Nagendra Nath Yadav、Sandip Sengupta、Basi V. Subba Reddy

  DOI：10.1002/hlca.201300035

  日期：2013.10

  A divergent synthesis of siphonarienal, siphonarienone, and pectinatone has been achieved from a common precursor 4, which was synthesized by using an enzymatic desymmetrization approach. The major key steps involved were Grignard reaction, Wittig reaction, Evans' asymmetric alkylation, and base‐catalyzed cyclization.

  从共同的前体4获得了虹吸烯醛，虹吸烯酮和果胶酮的发散合成，该前体4是通过酶促脱对称方法合成的。涉及的主要关键步骤是格利雅（Grignard）反应，维蒂希（Wittig）反应，埃文斯（Evans）的不对称烷基化和碱催化的环化反应。
• Isolation and synthesis of siphonarienal a new polypropionate from Siphonaria grisea
  作者：Manuel Norte、José J. Fernández、Agustín Padilla

  DOI：10.1016/s0040-4039(00)76923-1

  日期：1994.5

  Siphonarienal 1, a pentapropionate derivative, was isolated from the marine pulmonate mollusk Siphonaria grisea. Its structure was established on the basis of its spectroscopic data and its absolute configuration was assured by its enantioselective synthesis.

  Siphonarienal 1，一个五丙酸酯衍生物，从海洋软体动物有肺分离Siphonaria菌。根据其光谱数据确定其结构，并通过对映选择性合成确保其绝对构型。
• Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp <i>Trichogramma turkestanica</i>
  作者：Danny Geerdink、Jeffrey Buter、Teris A van Beek、Adriaan J Minnaard

  DOI：10.3762/bjoc.10.71

  日期：——

  Virgin females of the parasitoid wasp Trichogramma turkestanica produce minute amounts of a sex pheromone, the identity of which has not been fully established. The enantioselective synthesis of a putative component of this pheromone, (6S,8S,10S)-4,6,8,10-tetramethyltrideca-2E,4E-dien-1-ol (2), is reported as a contribution to this identification. Catalytic asymmetric conjugate addition of methylmagnesium bromide and stereoselective Horner–Wadsworth–Emmons olefinations are used as the key steps, and 2 was obtained in 16 steps with an overall yield of 4.4%.

  寄生性蜂Trichogramma turkestanica的处女雌性产生微量的性信息素，其身份尚未完全确定。这篇文章报告了一种假定为该信息素成分的(6S,8S,10S)-4,6,8,10-四甲基十三烯-2E,4E-二醇(2)的对映选择性合成，作为对其鉴定的贡献。催化不对称共轭加成甲基溴化镁和立体选择性Horner–Wadsworth–Emmons烯烃化反应被用作关键步骤，2经过16个步骤得到，总收率为4.4%。
• Structure elucidation of female-specific volatiles released by the parasitoid wasp <i>Trichogramma turkestanica</i> (Hymenoptera: Trichogrammatidae)
  作者：Armin Tröger、Teris A van Beek、Martinus E Huigens、Isabel M M S Silva、Maarten A Posthumus、Wittko Francke

  DOI：10.3762/bjoc.10.72

  日期：——

  Females of the parasitoid wasp Trichogramma turkestanica produce the putative polydeoxypropionates (2E,4E,6S,8S,10S)-4,6,8,10-tetramethyltrideca-2,4-diene and (2E,4E,6S,8S,10S)-4,6,8,10-tetramethyltrideca-2,4-dien-1-ol or their enantiomers as sex specific volatiles. The structures were assigned on the basis of GC–MS investigations using synthetic reference compounds.

  寄生性蜂Trichogramma turkestanica的雌性个体产生假定的聚脱氧丙酸酯(2E,4E,6S,8S,10S)-4,6,8,10-四甲基三十二碳烯和(2E,4E,6S,8S,10S)-4,6,8,10-四甲基三十二碳烯-1-醇或其对映体作为性别特异挥发物。这些结构是基于使用合成参考化合物进行的GC-MS调查而确定的。
• Total synthesis of the marine polypropionates, siphonarienal, siphonarienone, and pectinatone
  作者：Gowravaram Sabitha、Peddabuddi Gopal、Jhillu S. Yadav

  DOI：10.1016/j.tetasy.2009.08.021

  日期：2009.10

  The synthesis of the marine natural products, siphonarienal, siphonarienone, and pectinatone is described employing desymmetrization strategy to create three consecutive stereogenic centers. The key intermediate 7 was made by asymmetric hydroboration of the known meso-olefin using (−)-IPC2BH followed by PCC and Baeyer-Villiger oxidation reactions.

  利用去对称化策略创建了三个连续的立体生成中心，介绍了海洋天然产物虹吸管烯醛，虹吸管烯酮和果胶酮的合成。关键中间体7是通过使用（-）-IPC 2 BH对已知内消旋烯烃进行不对称硼氢化，然后进行PCC和Baeyer-Villiger氧化反应制得的。