(E)-6-triethylsilylhex-5-en-2-one | 440665-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-6-triethylsilylhex-5-en-2-one
• CAS: 440665-57-6
• 化学式: C₁₂H₂₄OSi
• 分子量: 212.407
• InChiKey: JUASCNVBVDKMAQ-PKNBQFBNSA-N

物化性质

• 沸点：
  274.8±23.0 °C(Predicted)
• 密度：
  0.839±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  14.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-6-triethylsilylhex-5-en-2-one 在 N-氯代丁二酰亚胺 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 7.5h， 生成 1-triethylsilyl-5-methyl-2-methylenepyrrolizidine
  参考文献：
  名称：

  Stereoselective synthesis of 2-methylenepyrrolizidines by tandem cyclization of N-propargylaminyl radicals

  摘要：

  Tandem cyclization of N-propargylaminyl radicals, generated by N-chlorination of (E)-alk-4-enylamines 2a-d and 2f followed by treatment with tributyltin radical, afforded 2-methylenepyrrolizidines 3a-d and 3f in a highly stereoselective manner. A similar radical cyclization of (Z)-N-propargyl-1-methyl-5-phenylpent-4-enylamine (2e) gave pyrrolizidine 3b having the same stereochemistry as that obtained from the E isomer 2b. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01613-7
• 作为产物：
  描述：

  三乙基硅烷 、 5-己炔-2-酮 在 dihydrogen hexachloroplatinate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以61%的产率得到(E)-6-triethylsilylhex-5-en-2-one
  参考文献：
  名称：

  Stereoselective synthesis of 2-methylenepyrrolizidines by tandem cyclization of N-propargylaminyl radicals

  摘要：

  Tandem cyclization of N-propargylaminyl radicals, generated by N-chlorination of (E)-alk-4-enylamines 2a-d and 2f followed by treatment with tributyltin radical, afforded 2-methylenepyrrolizidines 3a-d and 3f in a highly stereoselective manner. A similar radical cyclization of (Z)-N-propargyl-1-methyl-5-phenylpent-4-enylamine (2e) gave pyrrolizidine 3b having the same stereochemistry as that obtained from the E isomer 2b. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01613-7

文献信息

• Iridium-Catalyzed (<i>Z</i>)-Trialkylsilylation of Terminal Olefins
  作者：Biao Lu、J. R. Falck

  DOI：10.1021/jo902678p

  日期：2010.3.5

  A complex of commercial [Ir(OMe)(cod)](2) and 4,4-di-tert-butyl-2,2-bipyridine (dtbpy) catalyzes the Z-selective, dehydrative silylation of terminal alkenes, but not 1,2-disubstituted alkenes, with triethylsilane or benzyldimethylsilane in THF at 40 degrees C. Yields and Z-stereoselectivity were significantly improved by 2-norbornene, in contrast with other sacrificial alkenes. The reaction is compatible with many functional groups including epoxides, ketones, amides, alcohols, esters, halides, ketals, and sillanes. alpha,beta-Unsaturated esters were unreactive. The reaction probably proceeds through a Heck-type mechanism.
• Stereoselective synthesis of 2-methylenepyrrolizidines by tandem cyclization of N-propargylaminyl radicals
  作者：Hikaru Hasegawa、Hisanori Senboku、Yoshinori Kajizuka、Kazuhiko Orito、Masao Tokuda

  DOI：10.1016/s0040-4020(02)01613-7

  日期：2003.2

  Tandem cyclization of N-propargylaminyl radicals, generated by N-chlorination of (E)-alk-4-enylamines 2a-d and 2f followed by treatment with tributyltin radical, afforded 2-methylenepyrrolizidines 3a-d and 3f in a highly stereoselective manner. A similar radical cyclization of (Z)-N-propargyl-1-methyl-5-phenylpent-4-enylamine (2e) gave pyrrolizidine 3b having the same stereochemistry as that obtained from the E isomer 2b. (C) 2003 Elsevier Science Ltd. All rights reserved.