(2S,4S,6S)-2,4,6-trimethyl-1-nonanal | 174627-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,6S)-2,4,6-trimethyl-1-nonanal
• 英文别名: (2S,4S,6S)-2,4,6-trimethylnonanal
• CAS: 174627-66-8
• 化学式: C₁₂H₂₄O
• 分子量: 184.322
• InChiKey: UNGHCGVRGVTXFJ-SRVKXCTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (2S,4S,6S)-2,4,6-trimethyl-1-nonanal 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 0.5h， 生成 siphonarienal
  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 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 lithium aluminium tetrahydride 、 碘苯二乙酸 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (2S,4S,6S)-2,4,6-trimethyl-1-nonanal
  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。
• Asymmetric Conjugate Addition for the Preparation of <i>s</i><i>yn</i>-1,3-Dimethyl Arrays:  Synthesis and Structure Elucidation of Capensifuranone
  作者：David R. Williams、Andrea L. Nold、Richard J. Mullins

  DOI：10.1021/jo049567e

  日期：2004.8.1

  capensifuranone (1) has been achieved by the application of developments for asymmetric conjugate addition reactions of organocopper reagents with nonracemic N-enoyl-4-phenyl-1,3-oxazolidinones for the preparation of 1,3-syn-dimethyl arrays. The assignment of relative and absolute stereochemistry of 1 has been made following the high-field NMR characterizations of synthetic diol derivatives. The previously

  己烯呋喃酮（1）的合成已通过应用有机铜试剂与非外消旋N-烯酰基-4-苯基-1,3-恶唑烷酮的不对称共轭加成反应的进展来制备1,3-顺二甲基阵列而实现。根据合成二醇衍生物的高场NMR表征，确定了1的相对和绝对立体化学。先前未分配的C 4立体化学1被确定为（S）-构型。己烯呋喃酮及其C 4非对映异构体的热力学平衡已得到检验。
• 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。
• Application of Conformation Design in Acyclic Stereoselection:  Total Synthesis of Borrelidin as the Crystalline Benzene Solvate
  作者：Stephen Hanessian、Yang、Simon Giroux、Vincent Mascitti、Jianguo Ma、Franck Raeppel

  DOI：10.1021/ja030139k

  日期：2003.11.1

  The total synthesis of (-)-borrelidin (treponemycin), a structurally distinct 18-membered macrolide antibiotic, has been achieved. It was isolated as the crystalline benzene solvate, and its structure was confirmed by a single-crystal X-ray analysis. The deoxypropionate subunit consisting of four alternating C-methyl groups with a C(4)-C(10) syn/syn/anti orientation was elaborated by a new method of

  (-)-疏螺旋体素（密螺旋体霉素）的全合成，一种结构独特的 18 元大环内酯抗生素，已经实现。它被分离为结晶苯溶剂化物，其结构由单晶 X 射线分析证实。脱氧丙酸亚基由四个交替的 C-甲基基团组成，具有 C(4)-C(10) 顺/顺/反取向，是通过一种新方法对无环 α、β-不饱和酯进行迭代加成，依赖于两个连续的1,3-诱导并以 d-甘油醛作为手性祖体开始。独特的 Z/E 氰基二烯单元是通过应用 Still-Gennari 烯化协议作为单一异构体获得的。γ-羟基环戊烷羧酸亚单元由 L-苹果酸利用 C-乙烯基和 C-烯丙基的顺序引入制备，通过 Grubbs 闭环复分解反应利用无环 α,β-不饱和酯中的 1,2-诱导和碳环化。铜酸盐添加物中 1,3-syn-disposed 脱氧丙酸酯三联体的普遍性基于最小化过渡态中的同戊烷相互作用而合理化。虚拟金刚石晶格被用作描绘无环基材的低能量构象的可视化工具，并通过
• 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%。