dimethyl 4-methylene-2,2-bis(tributylstannylmethyl)pentanedioate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl 4-methylene-2,2-bis(tributylstannylmethyl)pentanedioate
• 化学式: C₃₄H₆₈O₄Sn₂
• 分子量: 778.332
• InChiKey: YKPNWAAAQRXBFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-丁-2-烯二腈 、 2-[(三丁基锡烷基)甲基]-2-丙烯酸甲酯 在 偶氮二异丁腈 、 盐酸 作用下， 以 苯 、 乙腈 为溶剂， 反应 4.33h， 以76%的产率得到methyl 2-(2,3-dicyanopropyl)acrylate
  参考文献：
  名称：

  Allylstannylation of Carbon−Carbon and Carbon−Oxygen Unsaturated Bonds via a Radical Chain Process¹

  摘要：

  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.

  DOI：

  10.1021/jo0057295

文献信息

• 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.