(S)-3,7-dimethyl-6-octenyl tosylate | 41144-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3,7-dimethyl-6-octenyl tosylate
• 英文别名: (S)-3,7-dimethyl-6-octene-1-ol 4'-methylbenzenesulfonate；(S)-3,7-dimethyloct-6-enyl 4-methylbenzenesulfonate；(3S)-3,7-dimethyl-6-octenyl p-toluenesulfonate；(3S)-3,7-dimethyl-6-octenyl-p-toluenesulfonate；(S)-3,7-dimethyloct-6-enyl toluenesulfonate；(3S)-3,7-Dimethyl-6-octenyltosylate；(s)-Citronellyltosylate；[(3S)-3,7-dimethyloct-6-enyl] 4-methylbenzenesulfonate
• CAS: 41144-01-8；67214-54-4；93303-23-2；116661-43-9
• 化学式: C₁₇H₂₆O₃S
• 分子量: 310.458
• InChiKey: DHXRPLSCJHVSLR-HNNXBMFYSA-N

物化性质

• 沸点：
  428.0±24.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3,7-dimethyl-6-octenyl tosylate 在 sodium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-(+)-溴化香茅酯
  参考文献：
  名称：

  Synthesis of the spiroacetal parts of spirofungin A and B

  摘要：

  The C9-C20 spiroacetal parts of spirofungin A and B, antifungal antibiotics from Strephomyces violaceusniger Tu 4113, were synthesized simultaneously from (S)-citronellyl bromide and (+/-)-epoxy alcohol via alkyne-lactone coupling reaction and diastereomeric separation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00371-3
• 作为产物：
  描述：

  香叶醇 在 Ru(OAc)2((S)-BINAP) 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、10.34 MPa 条件下， 反应 30.0h， 生成 (S)-3,7-dimethyl-6-octenyl tosylate
  参考文献：
  名称：

  Total Synthesis of Papulacandin D

  摘要：

  A total synthesis of the antifungal agent papulacandin D is reported. The molecule is representative of a large class of C-aryl glycosides that exhibit significant antifungal activity. The synthetic strategy bifurcates the molecule into two nearly equal subunits, the arylglycoside and 18-carbon fatty acid side chain. The key strategic transformations are (1) the palladium catalyzed, organosilanolate-based cross-coupling of a protected glucal silanol and (2) a catalytic enantioselective allylation of a dienal using allyltrichlorosilane. The synthesis was accomplished in 31 steps overall from commercial starting materials to afford over 50 mg of the natural product.

  DOI：

  10.1021/ja070071z

文献信息

• Synthesis of All the Stereoisomers of 7-Methylheptadecane and 7,11-Dimethylheptadecane, the Female Sex Pheromone Components of the Spring Hemlock Looper and the Pitch Pine Looper
  作者：Yasuo Shirai、Masanori Seki、Kenji Mori

  DOI：10.1002/(sici)1099-0690(199911)1999:11<3139::aid-ejoc3139>3.0.co;2-8

  日期：1999.11

  the stereoisomers of 7-methylheptadecane (1) and 7,11-dimethylheptadecane (2) were synthesized by starting from the enantiomers of citronellol (3) and methyl 3-hydroxy-2-methylpropanonate (8), respectively. A short synthesis of meso-7,11-dimethylheptadecane [(7R,11S)-2] was achieved starting from meso-2,6-dimethylheptanedioic acid [(2R,6S)-21]. A mixture of (S)-1 and (7R,11S)-2 is the pheromone of the

  7-甲基十七烷 (1) 和 7,11-二甲基十七烷 (2) 的所有立体异构体都是从香茅醇 (3) 和 3-羟基-2-甲基丙酸甲酯 (8) 的对映异构体开始合成的。从内消旋 2,6-二甲基庚二酸 [(2R,6S)-21] 开始，实现了内消旋 7,11-二甲基十七烷 [(7R,11S)-2] 的短时间合成。(S)-1 和 (7R,11S)-2 的混合物是春天铁杉弯钩蛾 (Lambdina athasaria) 和松树弯针蛾 (L. pellucidaria) 的信息素。
• Synthesis of All the Stereoisomers of 6-Methyl-2-octadecanone, 14-Methyl-2-octadecanone, and 6,14-Dimethyl-2-octadecanone, Sex Pheromone Components of the<i>Lyclene dharma dharma</i>Moth, from the Enantiomers of Citronellal
  作者：Yasumasa SHIKICHI、Kenji MORI

  DOI：10.1271/bbb.120436

  日期：2012.10.23

  stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2-octadecanone, the female-produced sex pheromone components of the Lyclene dharma dharma moth. Three well-established procedures, the Wittig reaction, alkylation of alkynes, and acetoacetic ester synthesis, were employed for the carbon-carbon bond formation to connect the building blocks.

  香茅醛的对映异构体被转化为6-甲基-2-十八碳烯酮，14-甲基-2-十八碳烯酮和6,14-二甲基-2-十八碳烯酮的全部立体异构体，这是女性生产的Lyclene dharma dharma的性信息素成分。蛾。三种公认的方法，即Wittig反应，炔烃的烷基化和乙酰乙酸酯的合成，被用于碳-碳键的形成，以连接结构单元。
• Synthesis and biological evaluation of chemical tools for the study of Dolichol Linked Oligosaccharide Diphosphatase (DLODP)
  作者：Michaël Bosco、Ahmad Massarweh、Soria Iatmanen-Harbi、Ahmed Bouhss、Isabelle Chantret、Patricia Busca、Stuart E.H. Moore、Christine Gravier-Pelletier

  DOI：10.1016/j.ejmech.2016.10.013

  日期：2017.1

  Citronellyl- and solanesyl-based dolichol linked oligosaccharide (DLO) analogs were synthesized and tested along with undecaprenyl compounds for their ability to inhibit the release of [3H]OSP from [3H]DLO by mammalian liver DLO diphosphatase activity. Solanesyl (C45) and undecaprenyl (C55) compounds were 50–500 fold more potent than their citronellyl (C10)-based counterparts, indicating that the alkyl

  合成了基于香茅烷基和茄基的多羟基连接的寡糖（DLO）类似物，并与十一碳烯基化合物一起测试了它们通过哺乳动物肝脏DLO二磷酸酶活性抑制[ 3 H] OSP从[ 3 H] DLO释放的能力。茄尼基（C45）和十一碳烯基（C55）化合物的效价比其基于香茅醇（C10）的同类化合物强50-500倍，这表明烷基链长对活性至关重要。香茅基系列中化合物的相对效力不同于茄基系列，其中香茅基二磷酸的效力分别是香茅基-PP-Glc N Ac 2和香茅基-PP-Glc N Ac 2倍和3倍；而茄基-PP-GlcN Ac和茄基-PP-Glc N Ac 2的效力分别比茄基二磷酸酯高4倍和8倍。在抑制DLODP分析时，十一碳烯基-PP-Glc N Ac和细菌脂质II的效力比十一碳烯基二磷酸高8倍。因此，至少对于疏水性更高的化合物而言，二磷酸二酯比二磷酸单酯是DLODP分析更有效的抑制剂。这些结果表明，DLO而不是二磷酸
• Nickel/Cobalt-Catalyzed C(sp³)–C(sp³) Cross-Coupling of Alkyl Halides with Alkyl Tosylates
  作者：Kimihiro Komeyama、Takuya Michiyuki、Itaru Osaka

  DOI：10.1021/acscatal.9b03352

  日期：2019.10.4

  The C(sp3)–C(sp3) cross-coupling of alkyl halides with alkyl tosylates has been developed by employing a combination of nickel and nucleophilic cobalt catalysts in the presence of a manganese reductant. This method provides a straightforward route to a diverse set of not only secondary–primary but also primary–primary C(sp3)–C(sp3) linkages under mild conditions without using alkyl-metallic reagents

  烷基卤化物与甲苯磺酸烷基酯的C（sp 3）–C（sp 3）交叉偶联是通过在锰还原剂存在下使用镍和亲核钴催化剂的组合来开发的。这种方法为在温和条件下不使用烷基金属试剂的情况下，不仅可以实现二级（一级）连接，而且还可以一级至一级（一级）C（sp 3）-C（sp 3）连接提供了直接的途径。机理研究表明，烷基卤化物和烷基甲苯磺酸盐均可形成烷基。另外，交叉偶联可用于组蛋白脱乙酰基酶抑制剂Vorinostat的短期合成。
• Composition of the Cloacal Gland Secretion of Tuatara,<i>Sphenodon punctatus</i>
  作者：Birte Flachsbarth、Matthias Fritzsche、Paul J. Weldon、Stefan Schulz

  DOI：10.1002/cbdv.200800265

  日期：2009.1

  secretions revealed triacylglycerols as major glandular constituents. Twelve major medium-chain fatty acids were found to be conjugated to glycerol in different combinations, resulting in complex mixtures. These acids were identified by transesterification and subsequent derivatization of natural samples, and their structures were verified by synthesis. The natural glycerides contain predominantly three of

  研究了at（Sphenodon punctatus）的泄殖腔分泌物的亲脂性含量。分泌物的CH2Cl2提取物的GC / EI-MS分析表明，三酰基甘油是腺体的主要成分。发现十二种主要的中链脂肪酸以不同的组合与甘油结合，形成复杂的混合物。这些酸通过酯交换反应和随后的天然样品衍生化来鉴定，其结构通过合成验证。天然甘油酯主要包含以下三种酸：辛酸（A），（E）-和（Z）-辛-4-烯酸（B和C，分别），（4E，6Z）-辛基-4,6 -二烯二酸（丁二酸; D），（R）-2,6-二甲基庚酸（E），（R）-2,6-二甲基庚-5-烯酸（F），（Z）-dec-4-烯酸（G ），（4Z，7Z）-癸-4,7-二烯酸（H），（R）-3,7-二甲基辛-6-烯酸（I），（R）-4，8-二甲基非-7-烯酸（J），（2R，6S）-2,6,10-三甲基十一烷基-9-烯酸（K）和（2R，5E）-2,6,10-三甲基十一烯-5,9