5-(tert-butyldiphenylsiloxy)-1,2-pentadiene | 190715-43-6

• 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: 5-(tert-butyldiphenylsiloxy)-1,2-pentadiene
• CAS: 190715-43-6
• 化学式: C₂₁H₂₆OSi
• 分子量: 322.522
• InChiKey: QNOXBDCNMWEUGU-UHFFFAOYSA-N

物化性质

• 沸点：
  377.7±25.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (碘乙炔基)苯 、 5-(tert-butyldiphenylsiloxy)-1,2-pentadiene 在 Schwartz's reagent 、 methylaluminoxane 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.33h， 以92%的产率得到tert-butyl-diphenyl-[(E)-7-phenylhept-3-en-6-ynoxy]silane
  参考文献：
  名称：

  1-碘炔与烯丙基锆的反应：通过烯丙基锆生成亚烷基类胡萝卜素

  摘要：

  通过烯丙基加氢锆化生成的烯丙基锆物种在甲基铝氧烷（MAO）存在下与1-碘代炔烃反应，生成烯丙基的碘化物取代产物。对2-（碘乙炔基）萘的标记研究表明，该反应涉及碘代炔烃的烯丙基锆化反应，生成经过1,2-重排的亚烷基类胡萝卜素。

  DOI：

  10.1016/s0040-4039(99)00296-8
• 作为产物：
  描述：

  聚合甲醛 、 (3-丁炔-1-基氧基)(2-甲基-2-丙基)二苯基硅烷 在 二异丙胺 、 copper(I) bromide 作用下， 以 1,4-二氧六环 为溶剂， 以40%的产率得到5-(tert-butyldiphenylsiloxy)-1,2-pentadiene
  参考文献：
  名称：

  Regiocontrolled Addition of Arylboronic Acids to Allenes Using Palladium and Platinum Catalysts

  摘要：

  Studies about the regiocontrolled addition of arylboronic acids to allenes using a palladium or a platinum catalyst have been described. The selectivity of the reaction can be altered by the choice of the metal reagent and base. Contrary to the formation of endo-olefinic products in the reactions using hydroxopalladium complex, predominant production of exo-olefinic products was observed by the reaction with hydroxoplatinum complex.

  DOI：

  10.1021/ol8021484

文献信息

• Copper-Catalyzed Regiodivergent Silacarboxylation of Allenes with Carbon Dioxide and a Silylborane
  作者：Yosuke Tani、Tetsuaki Fujihara、Jun Terao、Yasushi Tsuji

  DOI：10.1021/ja512040c

  日期：2014.12.24

  A regiodivergent silacarboxylation of allenes under a CO2 atmosphere with PhMe2Si-B(pin) as a silicon source in the presence of a copper catalyst at 70 °C has been developed. The regioselectivity of the reaction is successfully reversed by the proper choice of ligand; carboxylated vinylsilanes are obtained with rac-Me-DuPhos as the ligand, whereas the use of PCy3 affords carboxylated allylsilanes.

  在 70 °C 下，在铜催化剂存在下，以 PhMe2Si-B(pin) 作为硅源，在 CO2 气氛下开发了丙二烯的区域发散硅羧化反应。反应的区域选择性通过适当的配体选择成功逆转; 使用 rac-Me-DuPhos 作为配体获得羧化乙烯基硅烷，而使用 PCy3 获得羧化烯丙基硅烷。因此，可以从单个丙二烯底物选择性地和区域发散地合成两种不同的羧化硅烷。
• Nickel-iminophosphine-catalyzed [4+2] cycloaddition of enones with allenes: synthesis of highly substituted dihydropyrans
  作者：Saori Sako、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1039/c1cc10890e

  日期：——

  Enones were found to react with allenes intermolecularly in the presence of a catalytic amount of a nickel-iminophosphine complex to provide dihydropyrans via oxidative cyclization of an enone and Ni(0).

  发现在催化量的镍-亚氨基膦配合物的存在下，烯酮与烯类之间发生分子间反应，从而通过烯酮和Ni（0）的氧化环化作用提供二氢吡喃。
• Unusual Regioselectivity in the Reductive Coupling of Alkynes and Allenes by Hydrozirconation and Zinca-Claisen Rearrangement
  作者：Keisuke Suzuki、Takahiro Imai、Shigeo Yamanoi、Masao Chino、Takashi Matsumoto

  DOI：10.1002/anie.199724691

  日期：1997.12.1
• MAO-Catalyzed Allylzirconation of 1-Alkynes
  作者：Shigeo Yamanoi、Takahiro Imai、Takashi Matsumoto、Keisuke Suzuki*

  DOI：10.1016/s0040-4039(97)00527-3

  日期：1997.4

  A regio- and stereocontrolled method for the allylmetallation of 1-alkynes is described. The allylzirconium species, generated by hydrozirconation of allenes, undergo regioselective addition to 1-alkynes in the presence of oganoaluminum reagents among which methylaluminoxane (MAO) is particularly effective. (C) 1997 Elsevier Science Ltd.
• Regioselectivity of MAO-catalyzed allylmetallation of conjugated enynes with allylzirconiums
  作者：Shigeo Yamanoi、Takashi Matsumoto、Keisuke Suzuki

  DOI：10.1016/s0040-4039(98)02236-9

  日期：1998.12

  Various conjugated enynes 1 were subjected to the MAO-catalyzed reaction with the allylzirconium, generated by hydrozirconation of allenes. In light of the regiochemisty, the C-C bond formation occurs exclusively between the alpha carbon of the allylzirconium and the "yne" part of the conjugated enyne 1. Steric demand of the alpha-substituent X in 1 is the decisive factor for determing the the reactive site for 1. (C) 1998 Elsevier Science Ltd. All rights reserved.