3-trimethylsilyloxy-1-octyne | 73061-39-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-trimethylsilyloxy-1-octyne
• 英文别名: trimethyl(oct-1-yn-3-yloxy)silane
• CAS: 73061-39-9
• 化学式: C₁₁H₂₂OSi
• 分子量: 198.381
• InChiKey: OFIOMFMZMGLDCU-UHFFFAOYSA-N

物化性质

• 沸点：
  63-64 °C(Press: 4 Torr)
• 密度：
  0.839±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-trimethylsilyloxy-1-octyne 在 四氯化硅 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以76%的产率得到3-iodooct-1-yne
  参考文献：
  名称：

  NaI存在下的氯化硅是有用的系统，可用于将TMS，TBDMS和THP醚有效和选择性地转化为其相应的碘化物

  摘要：

  描述了使用SiO 2 -Cl / NaI系统将苄基，烯丙基和炔丙基TMS，TBDMS和THP醚直接且高度选择性地转化为相应的碘化物。反应在室温下在CH 3 CN中进行。在类似的反应条件下，脂族甲硅烷基和四氢吡喃基醚几乎保持完整。

  DOI：

  10.1016/s0040-4039(02)01706-9
• 作为产物：
  描述：

  1-辛炔-3-醇 、 叠氮基三甲基硅烷 在 四丁基溴化铵 作用下， 反应 0.17h， 以98%的产率得到3-trimethylsilyloxy-1-octyne
  参考文献：
  名称：

  Efficient O-Trimethylsilylation of Alcohols and Phenols with Trimethylsilyl Azide Catalyzed by Tetrabutylammonium Bromide under Neat Conditions

  摘要：

  A very efficient procedure for the trimethylsilylation of a wide variety of alcohols, including primary, allylic, benzylic, secondary, hindered secondary, tertiary, and phenols is reported. The reactions were carried out under neat conditions with trimethylsilyl azide (TMSN3) and, when necessary, in the presence of a catalytic amount (20 mol %) of tetrabutylammonium bromide (TBABr) at 30 or 70 degreesC. Under catalytic conditions, the yields of the corresponding trimethylsilyl ethers were greater than 91%. This procedure also allows the selective protection of primary and secondary alcohols in the presence of tertiary ones.

  DOI：

  10.1021/jo015814s

文献信息

• Indium-catalyzed annulation of 3-aryl- and 3-heteroarylindoles with propargyl ethers: synthesis and photoluminescent properties of aryl- and heteroaryl[c]carbazoles
  作者：Yuta Nagase、Hiroyuki Shirai、Masayoshi Kaneko、Eiji Shirakawa、Teruhisa Tsuchimoto

  DOI：10.1039/c3ob27407a

  日期：——

  Treatment of 3-aryl- and 3-heteroarylindoles with propargyl ethers under indium catalysis successfully provided aryl- and heteroaryl[c]carbazoles, which were found to be more efficient emitters compared with the corresponding [a]-analogs.

  用铜催化的炔丙基醚处理3-芳基和3-杂芳基吲哚，成功合成了芳基和杂芳基[c]卡巴唑，发现它们的发射效率比相应的[a]类物质更高。
• S_N2′ Boron-Mediated Mitsunobu Reactions - A New One-Pot Three-Component Synthesis of Substituted Enamides and Enol Benzoates
  作者：Fabienne Berrée、Nicolas Gernigon、Alain Hercouet、Chia Hui Lin、Bertrand Carboni

  DOI：10.1002/ejoc.200800965

  日期：2009.1

  The conversion of (3-hydroxy-1-propen-1-yl)boronates to substituted enamides and enol benzoates is readily achieved in a one-pot procedure consisting of a regiocontrolled Mitsunobu reaction with convenient nucleophiles, followed by allylboration of aldehydes. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  (3-羟基-1-丙烯-1-基)硼酸酯转化为取代的烯酰胺和烯醇苯甲酸酯可以在一锅法中轻松实现，该程序由区域控制的Mitsunobu反应与方便的亲核试剂组成，然后是醛的烯丙基硼化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Process for the preparation of cyclopentanoids and novel intermediates
  申请人：Board of Governors of Wayne State University

  公开号：US04873360A1

  公开（公告）日：1989-10-10

  Cyclopentanoids (I) of the formula: ##STR1## including stereoisomers are described along with a process for the preparation of I. In particular the preparation of prostanoids of the formula: ##STR2## wherein R.sub.1 is a alkyl group containing 1 to 8 carbon atoms and R.sub.2 CO.sub.2 R.sub.3 is an alkenyl ester group, R.sub.2 contains 2 to 6 carbon atoms and R.sub.3 is a lower alkyl group containing 1 to 6 carbon atoms is described. A particular prostaglandin prepared by the process is PGE.sub.2. The prostanoids have been demonstrated to have pharmacological activity in animals and humans. Novel intermediates of (I) are also described.

  本文介绍了公式为：##STR1##的环戊烷衍生物（I），包括立体异构体，以及制备I的方法。特别地，介绍了公式为：##STR2##的前列腺素类物质的制备方法，其中，R.sub.1是含有1到8个碳原子的烷基，R.sub.2 CO.sub.2 R.sub.3是烯基酯基，R.sub.2含有2到6个碳原子，R.sub.3是含有1到6个碳原子的低级烷基。其中，通过该方法制备的一种前列腺素是PGE.sub.2。这些前列腺素类物质已被证明在动物和人类中具有药理活性。本文还介绍了(I)的新型中间体。
• Lee, Adam Shih-Yuan; Yeh, Hsiu-Chih; Yeh, Ming-Kuo, Journal of the Chinese Chemical Society, 1995, vol. 42, # 6, p. 919 - 922
  作者：Lee, Adam Shih-Yuan、Yeh, Hsiu-Chih、Yeh, Ming-Kuo、Tsai, Ming-Hung

  DOI：——

  日期：——
• Nickel-catalyzed conjugate addition of alkynyl groups to .alpha.,.beta.-unsaturated ketones
  作者：Jeffrey Schwartz、Denise B. Carr、Robert T. Hansen、Fabian M. Dayrit

  DOI：10.1021/jo01303a024

  日期：1980.7