2-cyanoallyltributyltin | 119813-60-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: 2-cyanoallyltributyltin
• 英文别名: 2-cyanoallyltri-n-butylstannane；2-cyanoprop-2-enyltributyltin；2-(tributylstannylmethyl)acrylonitrile
• CAS: 119813-60-4
• 化学式: C₁₆H₃₁NSn
• 分子量: 356.139
• InChiKey: ANJJWTFZXOZESL-UHFFFAOYSA-N

物化性质

• 沸点：
  374.8±52.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-cyanoallyltributyltin 、 (E)-(1-Iodo-1-hexenyl)benzene 在 偶氮二异丁腈 作用下， 以 苯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Homolytic allylation of vinyl iodides with allylstananes

  摘要：

  In the presence of AIBN or Et3B, a variety of vinyl iodides reacted with allylstannanes bearing an electron-withdrawing group at the beta-position to afford 1,4-dienes in moderate to good yields. The allylation showed high stereoselectivity when the alpha-substituent of the iodides was a phenyl group, or the B-substituent was a bulky group. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01856-0
• 作为产物：
  描述：

  三正丁基氢锡 、 2-((phenylsulfonyl)methyl)acrylonitrile 在 catalyst: azoisobutyronitrile 作用下， 以 苯 为溶剂， 生成 2-cyanoallyltributyltin
  参考文献：
  名称：

  缩水甘油基当量与2-官能化烯丙基锡烷的反应

  摘要：

  2-溴-N-苯甲酰基甘氨酸甲酯与2-官能化的烯丙基锡烷试剂在自由基条件下的反应提供了一种以高收率获得α-烷基化氨基酸的新途径，这可以通过容易地合成4-亚甲基谷氨酸来举例说明。

  DOI：

  10.1039/c39880001030

文献信息

• Facile Introduction of Michael Acceptors into Nitrogen Heterocycles. A New Efficient Route to Fused α-Methylene-γ-lactams
  作者：Ryohei Yamaguchi、Katsunobu Mochizuki、Sinpei Kozima、Hidemasa Takaya

  DOI：10.1246/cl.1994.1809

  日期：1994.10

  A new effective method for introduction of Michael acceptors into isoquinoline and β-carboline systems has been developed by means of tin reagents. Deprotection of the N-allyloxycarbonyl-1-(2-methoxycarbonyl)prop-2-enyl adducts affords novel α-methylene-γ-lactams fused with isoquinoline and β-carboline systems.

  利用锡试剂开发了一种将迈克尔受体引入异喹啉和β-咔啉系统的有效方法。N-烯丙氧基羰基-1-(2-甲氧基羰基)丙-2-烯基加合物的脱保护提供了与异喹啉和β-咔啉系统融合的新型α-亚甲基-γ-内酰胺。
• Divergent change of regioselectivity in nucleophilic addition of electron deficient allylic tin reagents to 4-acylpyridinium salts; selective formation of 4,4-disubstituted 1,4-dihydropyridines
  作者：Ryohei Yamaguchi、Katsunobu Mochizuki、Sinpei Kozima、Hidemasa Takaya

  DOI：10.1039/c39930000981

  日期：——

  Nucleophilic additions of 2-methoxycarbonyl- and 2-cyano-allyltributyltins to 4-methoxycarbonyl-, 4-formyl-, and 4-acetyl-pyridines activated by methyl chloroformate afford 1,4-adducts exclusively or predominantly, while the reactions of 2-methylallyltributyltin with 4-methoxycarbonyl-and 4-acetyl-pyridines activated by methyl chloroformate give the 1,2-adducts exclusively.

  2-甲氧基羧酸基和2-氰基-烯丙基三丁基锡与由氯甲酸甲酯活化的4-甲氧基羧酸基、4-甲醛和4-乙酰基吡啶发生亲核加成反应，主要或专门生成1,4-加成产物，而2-甲基烯丙基三丁基锡与由氯甲酸甲酯活化的4-甲氧基羧酸基和4-乙酰基吡啶的反应则专门生成1,2-加成产物。
• Radical reactions of vinyl epoxides via radical translocations by a novel 1,5-n-Bu3Sn group or a 1,5-hydrogen atom transfer
  作者：Sunggak Kim、Sangphil Lee、Jae Suk Koh

  DOI：10.1021/ja00013a081

  日期：1991.6

  Radical reactions of vinyl epoxides with n-Bu 3 SnH proceed via radical translocations by a novel 1,5-n-Bu 3 Sn group or a 1,5-hydrogen atom transfer, provide access to allylic or other carbon centered radicals for use in cyclization or addition reaction, and are highly useful for the synthesis of a variety of carbocyclic compounds

  乙烯基环氧化物与 n-Bu 3 SnH 的自由基反应通过自由基易位进行，新的 1,5-n-Bu 3 Sn 基团或 1,5-氢原子转移，提供了获得烯丙基或其他碳中心自由基的途径，可用于环化或加成反应，对合成各种碳环化合物非常有用
• Allylstannylation of Carbon−Carbon and Carbon−Oxygen Unsaturated Bonds via a Radical Chain Process¹
  作者：Katsukiyo Miura、Hiroshi Saito、Daisuke Itoh、Toshie Matsuda、Naoki Fujisawa、Di Wang、Akira Hosomi

  DOI：10.1021/jo0057295

  日期：2001.5.1

  In the presence of a radical initiator, allyltributylstannanes bearing an electron-withdrawing group at the beta -position smoothly reacted with electron-deficient terminal alkenes to give allylstannylated products in good yields. The stannyl group was introduced into the terminal carbon with high regioselectivity. The allylstannylation of homochiral 8-phenylmenthyl acrylate proceeded with moderate to good diastereoselectivity. Terminal and electron-deficient internal alkynes as well efficiently underwent the radical-initiated allylstannylation in an anti addition mode. The reaction of terminal alkynes showed the same regioselectivity as that of terminal alkenes. The present radical reaction was applicable to allylation of aromatic aldehydes and ketones.
• BALDWIN, JACK E.;ADLINGTON, ROBERT M.;LOWE, CHRISTOPHER;ONEIL, IAN A.;SAN+, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 15, C. 1030-1031
  作者：BALDWIN, JACK E.、ADLINGTON, ROBERT M.、LOWE, CHRISTOPHER、ONEIL, IAN A.、SAN+

  DOI：——

  日期：——