(2S,6R)-2,6-dimethyloct-7-en-1-ol | 177567-65-6

• 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: (2S,6R)-2,6-dimethyloct-7-en-1-ol
• CAS: 177567-65-6
• 化学式: C₁₀H₂₀O
• 分子量: 156.268
• InChiKey: JHKNBWMXFBYOJB-UWVGGRQHSA-N

物化性质

• 沸点：
  217.9±19.0 °C(Predicted)
• 密度：
  0.835±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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,6R)-2,6-dimethyloct-7-en-1-ol 在 platinum on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 35.0h， 以87.9%的产率得到(2S,6S)-(-)-2,6-dimethyl-1-octanol
  参考文献：
  名称：

  Terpenes in organic synthesis

  摘要：

  All four stereoisomers of 2,6-dimethyloctan-1-ol, the nearest precursors of the title formates, were synthesized in five to eight stages, with configurational purity ranging from 41 to 96 %, employing a stereodivergent scheme based on the partial hydrolysis of two pseudoracemic substrates, (2RS,6R)-2,6-dimethyloct-1-yl formate and (2RS,6S)-2,6-dimethyloct-1-yl acetate, in the presence of porcine pancreatic lipase (PPL). Configurations and diastereomeric compositions of the alcohols thus obtained were determined by correlating the latter with (S,S)-4,8-dimethyldecanal, prepared on the basis of enantioselective biohydrogenation of (R)-2,6-dimethylocta-2,7-dienal with bakers' yeast, and by comparing the [alpha](D) values of the alcohols with their NMR data and/or with those of their (S)-MTPA derivatives. The attractant potency of stereoisomeric 2,6-dimethyloct-1-yl formates towards Tribolium confusum was found to vary depending on their diastereomeric composition. The configuration at C(6) exerts some influence on the stereoselectivity of the PPL-catalyzed hydrolysis of pseudoracemic 2,6-dimethyloct-1-yl formates.

  DOI：

  10.1007/bf01433762
• 作为产物：
  描述：

  7-(tert-butyldimethylsilyloxy)heptan-1-ol 在 sodium chlorite 、 sodium dihydrogenphosphate 、 锂硼氢 、 草酰氯 、 四丁基氟化铵 、 水 、 sodium hexamethyldisilazane 、 二甲基亚砜 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 25.25h， 生成 (2S,6R)-2,6-dimethyloct-7-en-1-ol
  参考文献：
  名称：

  Carolacton的合成研究：分子的C1-C8和C9-C19片段的对映选择性全合成

  摘要：

  摘要 本文描述了对carolacton的合成研究，carolacton是一种有效的抗龋齿和心内膜炎相关细菌的变形链球菌抗生素。通过使用手性库和醛醇缩醇策略的混合，可以合成具有多种功能化的酮酸侧链的12元内酯。碳链C1-C8是通过使用Paterson aldol方法和Corey-Fuchs反应获得的。C9–C19链是通过迭代的Evans不对称烷基化反应和E选择性交叉复分解反应制备的。 本文描述了对carolacton的合成研究，carolacton是一种有效的抗龋齿和心内膜炎相关细菌的变形链球菌抗生素。通过使用手性库和醛醇缩醇策略的混合，可以合成具有多种功能化的酮酸侧链的12元内酯。碳链C1-C8是通过使用Paterson aldol方法和Corey-Fuchs反应获得的。C9–C19链是通过迭代的Evans不对称烷基化反应和E选择性交叉复分解反应制备的。

  DOI：

  10.1055/s-0033-1339500

文献信息

• Total Synthesis of Carolacton and Demethylcarolactons with Potent Antiviral Activity
  作者：Haoyu Zhang、Bingsong Li、Hongzhi Yang、Ya Tan、Xu Tan、Yefeng Tang

  DOI：10.1021/acs.orglett.3c04038

  日期：2024.1.12

  potent inhibitory activity against various RNA viruses including SARS-CoV-2. Herein, we present a concise total synthesis of carolacton, featuring the Krische allylation, Marshall coupling, NHK coupling, and RCM reaction as key elements. Additionally, we have synthesized three simplified carolacton analogues, one of which, namely, 14-demethyl-carolacton, exhibited notable antiviral activity. The present

  Carolacton 是一种天然存在的 MTHFD1 抑制剂，对包括 SARS-CoV-2 在内的多种 RNA 病毒表现出有效的抑制活性。在此，我们提出了一种简明的 carolacton 全合成方法，以 Krische 烯丙基化、Marshall 偶联、NHK 偶联和 RCM 反应为关键要素。此外，我们还合成了三种简化的carolacton类似物，其中一种，即14-demethyl-carolacton，表现出显着的抗病毒活性。目前的工作为进一步探索 carolacton 及其类似物的治疗潜力铺平了道路。
• Studies toward the Total Synthesis of Carolacton
  作者：Gowravaram Sabitha、K. Shankaraiah、M. Prasad、Jhillu S. Yadav

  DOI：10.1055/s-0032-1317700

  日期：——

  An efficient synthesis of the C1-C19 segment of carolacton is described, starting from D-ribose, (-)-beta-citronellene and a homopropargylic alcohol, and which employs a Nozaki-Hiyama-Kishi (NHK) coupling as the key step. Other important steps are cross-metathesis and Evans aldol reactions.
• Synthetic Studies of Carolacton: Enantioselective Total Synthesis of C1-C8 and C9-C19 Fragments of the Molecule
  作者：Subhash Ghosh、Kulakarni Rao

  DOI：10.1055/s-0033-1339500

  日期：——

  prepared by means of iterative Evans asymmetric alkylations and an E-selective cross-metathesis reaction. This paper describes synthetic studies towards carolacton, a highly potent antibiotic against dental caries and endocarditis related bacterium Streptococcus mutans. The synthesis of the 12-membered lactone with a diversely functionalized keto acid side chain was accomplished by utilizing a blend of chiral

  摘要 本文描述了对carolacton的合成研究，carolacton是一种有效的抗龋齿和心内膜炎相关细菌的变形链球菌抗生素。通过使用手性库和醛醇缩醇策略的混合，可以合成具有多种功能化的酮酸侧链的12元内酯。碳链C1-C8是通过使用Paterson aldol方法和Corey-Fuchs反应获得的。C9–C19链是通过迭代的Evans不对称烷基化反应和E选择性交叉复分解反应制备的。 本文描述了对carolacton的合成研究，carolacton是一种有效的抗龋齿和心内膜炎相关细菌的变形链球菌抗生素。通过使用手性库和醛醇缩醇策略的混合，可以合成具有多种功能化的酮酸侧链的12元内酯。碳链C1-C8是通过使用Paterson aldol方法和Corey-Fuchs反应获得的。C9–C19链是通过迭代的Evans不对称烷基化反应和E选择性交叉复分解反应制备的。
• Terpenes in organic synthesis
  作者：G. D. Gamalevich、B. N. Morozov、E. P. Serebryakov

  DOI：10.1007/bf01433762

  日期：1996.1

  All four stereoisomers of 2,6-dimethyloctan-1-ol, the nearest precursors of the title formates, were synthesized in five to eight stages, with configurational purity ranging from 41 to 96 %, employing a stereodivergent scheme based on the partial hydrolysis of two pseudoracemic substrates, (2RS,6R)-2,6-dimethyloct-1-yl formate and (2RS,6S)-2,6-dimethyloct-1-yl acetate, in the presence of porcine pancreatic lipase (PPL). Configurations and diastereomeric compositions of the alcohols thus obtained were determined by correlating the latter with (S,S)-4,8-dimethyldecanal, prepared on the basis of enantioselective biohydrogenation of (R)-2,6-dimethylocta-2,7-dienal with bakers' yeast, and by comparing the [alpha](D) values of the alcohols with their NMR data and/or with those of their (S)-MTPA derivatives. The attractant potency of stereoisomeric 2,6-dimethyloct-1-yl formates towards Tribolium confusum was found to vary depending on their diastereomeric composition. The configuration at C(6) exerts some influence on the stereoselectivity of the PPL-catalyzed hydrolysis of pseudoracemic 2,6-dimethyloct-1-yl formates.