(3,7-dimethyloct-6-enyloxy)trimethylsilane | 18419-09-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3,7-dimethyloct-6-enyloxy)trimethylsilane
• 英文别名: 3,7-dimethyl-1-trimethylsilyloxy-6-octene；Citronelloxy-trimethylsilan；Silane, [(3,7-dimethyl-6-octenyl)oxy]trimethyl-；3,7-dimethyloct-6-enoxy(trimethyl)silane
• CAS: 18419-09-5
• 化学式: C₁₃H₂₈OSi
• 分子量: 228.45
• InChiKey: GIHFSHYTNPSBQF-UHFFFAOYSA-N

物化性质

• 沸点：
  90-91 °C(Press: 4.5 Torr)
• 密度：
  0.8395 g/cm3(Temp: 30 °C)
• 保留指数：
  1307.6

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  (3,7-dimethyloct-6-enyloxy)trimethylsilane 在 sodium acetate 、 1,2-bis(3,5-bis(trifluoromethyl)phenyl)diselane 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 0.5h， 以95%的产率得到[5-(3,3-Dimethyl-oxiranyl)-3-methyl-pentyloxy]-trimethyl-silane
  参考文献：
  名称：

  硒催化的过氧化氢水溶液氧化。第一部分：均相溶液中的环氧化反应

  摘要：

  一些 二硒 合成并测试了与水的环氧化反应中的催化活性 过氧化氢。 双[3,5-双（三氟甲基）苯基]二硒化物形成相应的3,5-二（三氟甲基）苯亚硒酸（L. Syper和J. Mlochowski，四面体，1987，43，207）在原位，它是一种高活性和选择性的催化剂 用于环氧化 烯烃 在 2,2,2-三氟乙醇。这是第一个有效的硒化合物（催化剂摩尔比s / c  = 200）催化敏感分子的形成环氧化物 以几乎定量的产量。

  DOI：

  10.1039/b008198l
• 作为产物：
  描述：

  lithium (2S,3S,4S,5R,6S)-6-(4-((4-((3,7-dimethyloct-6-enyloxy)(phenethoxy)methyl)phenylcarbamoyloxy)-methyl)phenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate 在 β-D-glucuronidase 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 生成 (3,7-dimethyloct-6-enyloxy)trimethylsilane
  参考文献：
  名称：

  A Structurally Simple Self-Immolative Reagent That Provides Three Distinct, Simultaneous Responses per Detection Event

  摘要：

  A general design is presented for a stimulus-responsive small molecule that is capable of responding to a specific applied chemical or physical signal by releasing two different types of pendant small molecules and a colorimetric indicator simultaneously. A key aspect of this design is the ease with which these reagents are prepared: typically, only four synthetic steps are required. Moreover, the modular construction strategy provides access to stimuli-responsive reagents that are capable of (i) responding to a variety of applied signals and (ii) releasing a number of different small molecules that contain primary alcohols, secondary alcohols, or phenols. These stimuli-responsive reagents are stable under physiological conditions (neither hydrolysis nor thermal degradation of the reagent occurs in significant quantity), and when they are exposed to the appropriate applied signal, they release both pendant small molecules and the colorimetric indicator completely within hours. Finally, unlike other functional groups, such as carbonates, that are used to connect alcohol-bearing molecules to controlled-release reagents, the linkage described in this article increases in hydrolytic stability (rather than decreases) as the plc of the pendant alcohol decreases.

  DOI：

  10.1021/jo2018763

文献信息

• Efficient and Convenient Procedure for Protection of Hydroxyl Groups to the THP, THF and TMS Ethers and Oxidation of these Ethers to their Aldehydes or Ketones in [BPy]FeCl₄ as a Low Cost Room Temperature Ionic Liquid
  作者：Ahmad R. Khosropour、Mohammad M. Khodaei、Sattar Ghaderi

  DOI：10.1515/znb-2006-0313

  日期：2006.3.1

  Alcohols were converted to the corresponding THP, THF or TMS ethers in high to excellent yields in 1-n-butylpyridinium chloroferrate media as a stable and low cost room temperature ionic liquid. In addition, oxidation of these ethers to their aldehydes or ketones without any overoxidation reactions in this ionic liquid was also performed.

  醇类在1-丁基吡啶氯铁介质中被转化为相应的THP、THF或TMS醚，产率高至极好。这是一种稳定且低成本的室温离子液体。此外，在这种离子液体中，这些醚被氧化为它们的醛或酮，而没有发生任何过氧化反应。
• Silylation of O–H bonds by catalytic dehydrogenative and decarboxylative coupling of alcohols with silyl formates
  作者：Clément Chauvier、Timothé Godou、Thibault Cantat

  DOI：10.1039/c7cc05212j

  日期：——

  Silylformates HCO₂SiR₃ are used for the first time as efficient silylating agents for alcohols, in the presence of a ruthenium molecular catalyst.

  Silylformates HCO₂SiR₃首次作为高效的硅烷化剂用于醇类，在钌分子催化剂的存在下。
• Selective Deprotection of the Diphenylmethylsilyl (DPMS) Hydroxyl Protecting Group under Environmentally Responsible, Aqueous Conditions
  作者：Nnamdi Akporji、Josh Lieberman、Michael Maser、Masahiko Yoshimura、Zarko Boskovic、Bruce H. Lipshutz

  DOI：10.1002/cctc.201901232

  日期：2019.12.5

  Two new methods for selective deprotection of diphenylmethylsilyl (DPMS) ethers are described. Unmasking can be achieved with either catalytic amounts of perfluoro‐1‐butanesulfonyl fluoride (a SuFEx reagent) under mild, aqueous micellar conditions, or using stoichiometric amounts of 18‐crown‐6 ether in aqueous ethanol.

  描述了两种新的选择性脱保护二苯基甲基甲硅烷基（DPMS）醚的方法。在温和的胶束水溶液条件下，可以使用催化量的全氟-1-丁烷磺酰氟（SuFEx试剂）或在乙醇水溶液中使用化学计量的18-冠-6醚来实现掩盖。
• Selective cleavage of ethers using silica-alumina gel catalysts prepared by the sol-gel method
  作者：Yoshihiko Matsumoto、Keisuke Mita、Keiji Hashimoto、Hideo Iio、Takashi Tokoroyama

  DOI：10.1016/0040-4020(96)00501-7

  日期：1996.7

  The selective cleavage of tetrahydropyranyl (THP), methoxymethyl (MOM), 1-ethoxyethyl (EE), 1-methyl-1-methoxyethyl (MME) and trimethylsilyl (TMS) ether groups with silica-alumina gels prepared by the sol-gel method has been investigated. The deprotection rate follows the order: TMS > MME ⪢ EE > THP ⪢ MOM. The selective deprotection of diol derivatives with mixed protecting groups was achieved efficiently

  用溶胶-凝胶法制备的二氧化硅-氧化铝凝胶选择性裂解四氢吡喃基（THP），甲氧基甲基（MOM），1-乙氧基乙基（EE），1-甲基-1-甲氧基乙基（MME）和三甲基甲硅烷基（TMS）醚基已被调查。脱保护率遵循以下顺序：TMS> MME⪢EE> THP⪢MOM。有效地实现了具有混合保护基的二醇衍生物的选择性脱保护。含有伯羟基和叔羟基的底物的Bis-THP和bis-MOM醚衍生物以中等选择性被单脱保护。还检查了甘油醚的选择性脱保护。因此显示出通过溶胶-凝胶法制备的二氧化硅-氧化铝凝胶是在温和条件下以简单方式选择性裂解醚保护基团以提供产物的良好催化剂。
• Afonso, Carlos M.; Barros, M. Teresa; Maycock, Christopher D., Journal of the Chemical Society. Perkin transactions I, 1987, p. 1221 - 1224
  作者：Afonso, Carlos M.、Barros, M. Teresa、Maycock, Christopher D.

  DOI：——

  日期：——