5-(tert-butyldimethylsilyl)-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-methylenepent-4-ynenitrile | 1011718-27-6

• 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-butyldimethylsilyl)-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-methylenepent-4-ynenitrile
• 英文别名: 4-tert-butyldimethylsilyl-2-[3-(tert-butyldimethylsiloxy)-1-cyano-prop-1-yl]-1-buten-3-yne；5-[Tert-butyl(dimethyl)silyl]-2-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-3-methylidenepent-4-ynenitrile；5-[tert-butyl(dimethyl)silyl]-2-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-3-methylidenepent-4-ynenitrile
• CAS: 1011718-27-6
• 化学式: C₂₀H₃₇NOSi₂
• 分子量: 363.691
• InChiKey: UJFHGUADMSQVPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-tert-butyldimethylsilyl-2-propynenitrile 、 tert-butyldimethyl(penta-3,4-dien-1-yloxy)silane 在 bis(1,5-cyclooctadiene)nickel (0) 、 三苯基硼烷 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 17.0h， 生成 5-(tert-butyldimethylsilyl)-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-methylenepent-4-ynenitrile 、 (Z)-4-tert-butyldimethylsilyl-6-(tert-butyldimethylsiloxy)-2-cyanomethyl-3-hexen-1-yne 、 (E)-4-tert-butyldimethylsilyl-6-(tert-butyldimethylsiloxy)-2-cyanomethyl-3-hexen-1-yne
  参考文献：
  名称：

  Alkynylcyanation of alkynes and dienes catalyzed by nickel

  摘要：

  Alkynyl cyanides are found to add across alkynes and 1,2-dienes in the presence of a catalyst prepared in situ from Ni(cod)(2), xantphos, and BPh3. A range of functionalized conjugated cis-enynes are obtained with high regioselectivity. The addition reaction across norbornadiene proceeds in the absence of BPh3 to give exo-cis adduct exclusively. A stoichiometric reaction of ail alkynyl cyanide, Ni(cod)2, xantphos, and BPh3 gives trans-(xantphos)Ni(CNBPh3)(C CSiMe(2)t-Bu), which is suggested to be a plausible reaction intermediate of the alkynylcyanation reaction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.079

文献信息

• Nickel/BPh3-Catalyzed Alkynylcyanation of Alkynes and 1,2-Dienes: An Efficient Route to Highly Functionalized Conjugated Enynes
  作者：Yoshiaki Nakao、Yasuhiro Hirata、Masaaki Tanaka、Tamejiro Hiyama

  DOI：10.1002/anie.200704095

  日期：2008.1
• Alkynylcyanation of alkynes and dienes catalyzed by nickel
  作者：Yasuhiro Hirata、Masaaki Tanaka、Akira Yada、Yoshiaki Nakao、Tamejiro Hiyama

  DOI：10.1016/j.tet.2009.03.079

  日期：2009.6

  Alkynyl cyanides are found to add across alkynes and 1,2-dienes in the presence of a catalyst prepared in situ from Ni(cod)(2), xantphos, and BPh3. A range of functionalized conjugated cis-enynes are obtained with high regioselectivity. The addition reaction across norbornadiene proceeds in the absence of BPh3 to give exo-cis adduct exclusively. A stoichiometric reaction of ail alkynyl cyanide, Ni(cod)2, xantphos, and BPh3 gives trans-(xantphos)Ni(CNBPh3)(C CSiMe(2)t-Bu), which is suggested to be a plausible reaction intermediate of the alkynylcyanation reaction. (C) 2009 Elsevier Ltd. All rights reserved.