(3S,6S)-3,6-dimethyloctane | 1730-95-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 饱和烃
• 英文名称: (3S,6S)-3,6-dimethyloctane
• 英文别名: (3S,6S)-3,6-dimethyl-octane；(+)(3S:6S)-3.6-dimethyl-octane；3.6-Dimethyl-octan,rechtsdrehende Form；(+)(3S:6S)-3.6-Dimethyl-octan；aktives Diamyl；(+)-(3S,6S)-3,6-Dimethyl-octan
• CAS: 1730-95-6
• 化学式: C₁₀H₂₂
• 分子量: 142.285
• InChiKey: JEEQUUSFXYRPRK-UWVGGRQHSA-N

物化性质

• 沸点：
  160 °C
• 密度：
  0.7357 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  3,6-dimethyl-oct-4-ene 在 镍 氢气 作用下， 25.0 ℃ 、101.32 kPa 条件下， 生成 (3S,6S)-3,6-dimethyloctane
  参考文献：
  名称：

  通过Wittig反应合成手性烯烃。

  摘要：

  DOI：

  10.1016/s0040-4039(01)92586-9

文献信息

• Pheromone synthesis. Part 243: Synthesis and biological evaluation of (3R,13R,1′S)-1′-ethyl-2′-methylpropyl 3,13-dimethylpentadecanoate, the major component of the sex pheromone of Paulownia bagworm, Clania variegata, and its stereoisomers
  作者：Kenji Mori、Takuya Tashiro、Boguang Zhao、David M. Suckling、Ashraf M. El-Sayed

  DOI：10.1016/j.tet.2010.02.028

  日期：2010.4

  All of the four stereoisomers of (1′S)-1′-ethyl-2′-methylpropyl 3,13-dimethylpentadecanoate, the major component of the female sex pheromone of Clania variegata, were synthesized by employing olefin cross metathesis as the key reaction and starting from (R)- or (S)-2-methyl-1-butanol, (R)- or (S)-citronellal, and (S)-2-methyl-3-pentanol. Their bioassay revealed the (3R,13R,1′S)-isomer as the bioactive

  3,13-二甲基十五烷酸（1 'S）-1'-乙基-2'-甲基丙基3,13-二甲基十五烷酸酯的四种立体异构体均以烯烃交叉复分解为关键反应合成（R）-或（S）-2-甲基-1-丁醇，（R）-或（S）-香茅醛和（S）-2-甲基-3-戊醇。他们的生物测定揭示了（3 R，13 R，1 'S）-异构体是具有生物活性的异构体，通过采用Wittig反应作为关键步骤，可以通过两种不同的方式实现更有效的合成。
• Pheromone synthesis. Part 240: Cross-metathesis with Grubbs I (but not Grubbs II) catalyst for the synthesis of (R)-trogodermal (14-methyl-8-hexadecenal) to study the optical rotatory powers of compounds with a terminal sec-butyl group
  作者：Kenji Mori

  DOI：10.1016/j.tet.2009.02.064

  日期：2009.5

  (R)-Trogodermal (14-methyl-8-hexadecenal), the sex pheromone of Trogoderma species of pest insects against stored products, and its (S)-isomer were synthesized by using olefin cross-metathesis between (R)- or (S)-7-methyl-1-nonene and 8-nonenyl acetate as the key step. This step was successful with Grubbs I but not with Grubbs II catalyst. The latter caused randomization of the carbon skeleton to give

  （- [R）-Trogodermal（14甲基-8-十六碳烯醛），性信息素斑皮蠹属对照存储产品害虫的种类，以及其（小号）通过使用烯烃之间（交叉复分解，合成异构体[R ）-或（S）-7-甲基-1-壬烯和乙酸8-壬烯酯是关键步骤。该步骤对于Grubbs I是成功的，但是对于Grubbs II催化剂却不是成功的。后者导致碳骨架的随机化，从而产生异常产物的混合物，该异常产物具有比所需产物更长或更短的碳链。测量了18种新的和6种先前合成的具有仲仲丁基端基的化合物的比旋光度，得出的结论是[α] D +3.5至+6.5或-3.6至-6.4
• Synthesis of all the four stereoisomers of (1′S)-1-ethyl-2-methylpropyl 3,13-dimethylpentadecanoate, the major component of the sex pheromone of Paulownia bagworm, Clania variegata
  作者：Kenji Mori、Takuya Tashiro

  DOI：10.1016/j.tetlet.2009.02.046

  日期：2009.7

  All the four stereoisomers of (1′S)-1-ethyl-2-methylpropyl 3,13-dimethylpentadecanoate, the major component of the sex pheromone of Clania variegata, were synthesized by starting from (R)- or (S)-2-methylbutan-1-ol, (R)- or (S)-citronellal, and (S)-2-methylpentan-3-ol. Olefin cross metathesis was employed as the key reaction.

  从（R）-或（S）-2开始合成（1 'S）-1-乙基-2-甲基丙基3,13-二甲基十五烷酸酯的全部四种立体异构体-甲基丁烷-1-醇，（R）-或（S）-香茅醛和（S）-2-甲基戊烷-3-醇。烯烃交叉复分解被用作关键反应。
• Low-Magnitude Mechanical Loading Becomes Osteogenic When Rest Is Inserted Between Each Load Cycle
  作者：Sundar Srinivasan、David A. Weimer、Steven C. Agans、Steven D. Bain、Ted S. Gross

  DOI：10.1359/jbmr.2002.17.9.1613

  日期：——

  Strategies to counteract bone loss with exercise have had fairly limited success, particularly those regimens subjecting the skeleton to mild activity such as walking. In contrast, here we show that it is possible to induce substantial bone formation with low‐magnitude loading. In two distinct in vivo models of bone adaptation, we found that insertion of a 10‐s rest interval between each load cycle transformed a locomotion‐like loading regime that minimally influenced osteoblast activity into a potent anabolic stimulus. In the avian ulna model, the minimal mean (+SE) periosteal labeled surface (Ps.LS) observed in the intact contralateral bones (1.6 ± 1.5%) was doubled after 3 consecutive days of low‐magnitude loading (3.8 ± 1.5%; p = 0.03). However, modifying the regimen by inserting 10 s of rest between each load cycle significantly enhanced the periosteal response (21.9 + 4.5%; p = 0.03). In the murine tibia model, 5 consecutive days of 100 low‐magnitude loading cycles did not significantly alter mean periosteal bone formation rate (BFR) compared with contralateral bones (0.011 ± 0.005 μm3/μm2 per day vs. 0.021 ± 0.013 μm3/μm2 per day). In contrast, separating each of 10 of the same loading cycles with 10 s of rest significantly elevated periosteal BFR (0.167 ± 0.049 μm3/μm2 per day; p = 0.01). Endocortical bone formation parameters were not altered by any loading regimen in either model. We conclude that 10 s of rest between each load cycle of a low‐magnitude loading protocol greatly enhances the osteogenic potential of the regimen.

  通过运动来抵消骨质流失的策略取得的成功相当有限，尤其是那些让骨骼进行轻微活动（如散步）的方案。与此相反，我们在这里展示了通过低强度负荷诱导大量骨形成的可能性。在两种不同的体内骨适应模型中，我们发现，在每个负荷周期之间插入 10 秒钟的休息时间，可将对成骨细胞活动影响最小的类似运动的负荷机制转变为一种强有力的合成代谢刺激。在鸟类尺骨模型中，连续 3 天的低强度加载后，在完整对侧骨中观察到的最小平均（+SE）骨膜标记面（Ps.LS）（1.6 ± 1.5%）增加了一倍（3.8 ± 1.5%；P = 0.03）。然而，通过在每个加载周期之间插入 10 秒钟的休息时间来改变加载方案，则可显著增强骨膜反应（21.9 + 4.5%；p = 0.03）。在小鼠胫骨模型中，与对侧骨（每天 0.011 ± 0.005 μm3/μm2 与每天 0.021 ± 0.013 μm3/μm2 相比）相比，连续 5 天 100 次低强度加载循环并不会显著改变平均骨膜骨形成率（BFR）。相比之下，在 10 个相同的加载周期中，每个周期休息 10 秒钟可显著提高骨膜 BFR（每天 0.167 ± 0.049 μm3/μm2; p = 0.01）。在这两种模型中，任何加载方案都不会改变皮质内骨形成参数。我们的结论是，在低强度加载方案的每个加载周期之间休息 10 秒可大大提高该方案的成骨潜力。
• Carpita, Adriano; Benetti, Massimo; Rossi, Renzo, Gazzetta Chimica Italiana, 1982, vol. 112, # 9/10, p. 415 - 420
  作者：Carpita, Adriano、Benetti, Massimo、Rossi, Renzo

  DOI：——

  日期：——