(Z)-3-methyl-5-trimethylsilylpent-2-en-4-yn-1-ol | 121635-19-6

• 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: (Z)-3-methyl-5-trimethylsilylpent-2-en-4-yn-1-ol
• CAS: 121635-19-6
• 化学式: C₉H₁₆OSi
• 分子量: 168.311
• InChiKey: VZZXLVVJVYRACD-UITAMQMPSA-N

物化性质

• 沸点：
  231.6±19.0 °C(Predicted)
• 密度：
  0.899±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  (Z)-3-methyl-5-trimethylsilylpent-2-en-4-yn-1-ol 在 甲醇 、 potassium carbonate 作用下， 以58%的产率得到(Z)-3-甲基戊-2-烯-4-炔-1-醇
  参考文献：
  名称：

  分子内吡啶酮/烯炔光环加成：[4 + 4]和[2 + 2]途径的划分

  摘要：

  1,3-烯炔和2-吡啶酮之间的分子内光环加成（> 290 nm）比分子间形式具有更高的选择性。三原子链接既控制区域化学作用，又分离[2 + 2]和[4 + 4]途径。已对所有四个头对头，头对尾，尾对头和尾对尾的系链进行了研究。连杆经由所述烯炔引线的烯[2 + 2]的产品，无论烯烃的几何形状，而连杆通过在[4 + 4]的cycloadducts炔结果。[4 + 4]环加成反应的桥联1,2,5-环辛三烯产物不稳定，并会随后发生[2 + 2]二聚反应。

  DOI：

  10.1021/ol200390j
• 作为产物：
  描述：

  在 cerium chloride heptahydrate 作用下， 生成 (Z)-3-methyl-5-trimethylsilylpent-2-en-4-yn-1-ol
  参考文献：
  名称：

  新型金（I）催化的二炔环化异构体对中等规模的环炔烃的异常访问

  摘要：

  炔烃的双重反应性：金（I）催化的1,9和1,10-二炔环异构化可以有效合成中型环炔烃。提议这种稀有的炔烃-炔烃偶联是通过将乙炔金亲核加成到金（I）活化的炔烃上来进行的。

  DOI：

  10.1002/chem.200901312

文献信息

• Electronic Tuning of Fischer Carbene Complexes in the Preparation of Bicyclo[3.1.1]heptanones as Taxane A-ring Synthons
  作者：Weiqin Jiang、Michael J Fuertes、William D Wulff

  DOI：10.1016/s0040-4020(99)01101-1

  日期：2000.4

  A synthetic route to taxol and other Taxus diterpenes is described which employs as a key step the reaction between a Fischer carbene complex and a 1,6 enyne to construct 1-substituted-7,7-dimethyl-2-methylenebicyclo[3.1.1] heptan-6-ones. It was found that the reaction between complex 2 and 7-methyl-3-methylene-6-octen-1-yne (dienyne 30) yielded a mixture of bicyclo[3.1.1]heptanone 35 and cyclobutenone 36, the latter possibly arising from the migration of the chromium fragment from an electron-rich alkene to a less electron-rich alkene in the vinyl carbene complex intermediate (i.e. 40-42). On this basis, it was expected that bicycloheptanone yields would increase with increasing electron deficiency in the intermediate 40 since this should lead to more competitive CO insertion. This was observed with a series of electronically modified carbene complexes (45 and 48a-d). The more electron deficient complexes gave good yields of bicycloheptanones, thus providing an efficient means for preparing taxane A-ring synthons. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthetic Studies toward Potent Cytotoxic Agent Amphidinolide B: Synthesis of the C₈-C₁₈ Fragment
  作者：T. K. Chakraborty

  DOI：10.1055/s-1999-2544

  日期：1999.1
• A New Co₂(CO)₈-Mediated Tandem [5 + 1]/[2 + 2 + 1]-Cycloaddition Reaction:  A One-Pot Synthesis of Tricyclic δ-Lactones from <i>cis</i>-Epoxy Ene-ynes
  作者：Arjan Odedra、Chang-Jung Wu、Reniguntala J. Madhushaw、Su-Lein Wang、Rai-Shung Liu

  DOI：10.1021/ja0346633

  日期：2003.8.1

  In the presence of Co2(CO)8 and CO, cis-epoxyalkynes bearing a tether olefin undergo a tandem [5 + 1]/[2 + 2 + 1]-cycloaddition to give tricyclic delta-lactones efficiently in a one-pot operation. The reaction mechanism is proposed to involve a cobalt-coordinated cyclic allene species.
• A new mild procedure for the direct coupling of 1-trimethylsilyl acetylenes with vinyl triflates or aryl iodide
  作者：Ulla Halbes、Patrick Pale

  DOI：10.1016/s0040-4039(02)00209-5

  日期：2002.3

  1-Trimethylsilyl acetylenes can be directly coupled with vinyl triflates or aryl iodide in the presence of the appropriate amount of potassium carbonate and methanol and a catalytic amount of AgCl and Pd(PPh3)(4). Functionalized enynes can thus be obtained in good to excellent yields without prior deprotection of the alkyne. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Bovicelli, P.; Mincione, E.; Parsons, P. J., Synthetic Communications, 1988, vol. 18, # 11, p. 1231 - 1240
  作者：Bovicelli, P.、Mincione, E.、Parsons, P. J.

  DOI：——

  日期：——