ethyl (E)-3-(tri-n-butylstannyl)-2-pentenoate | 942428-80-0

• 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: ethyl (E)-3-(tri-n-butylstannyl)-2-pentenoate
• 英文别名: ethyl (E)-3-tributylstannyl-2-pentenoate
• CAS: 942428-80-0；89474-80-6；89474-79-3
• 化学式: C₁₉H₃₈O₂Sn
• 分子量: 417.22
• InChiKey: RKMZCZLPFQMCTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-iodo-2-methoxy-3-methoxymethoxymethyl-6-(trimethylsilanyl)pyridine 、 ethyl (E)-3-(tri-n-butylstannyl)-2-pentenoate 在 四(三苯基膦)钯 copper(l) chloride 、 lithium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 17.0h， 以80%的产率得到(E)-3-[2-methoxy-3-methoxymethoxymethyl-6-(trimethylsilanyl)pyridin-4-yl]pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans

  摘要：

  An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00632-4
• 作为产物：
  描述：

  2-戊炔酸乙酯 、 三正丁基氢锡 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl (E)-2-tributylstannyl-2-pentenoate 、 ethyl (E)-3-(tri-n-butylstannyl)-2-pentenoate
  参考文献：
  名称：

  Synthetic Applications of Alkyl (E)-2-Tributylstannyl-2-alkenoates: Selective Synthesis of (S)-1-Methylbutyl (E)-2-Methyl-2-pentenoate, an Aggregation Pheromone Component ofRhyzopertha dominicaandProstephanus truncatus

  摘要：

  Stereoisomerically pure (S)-1-methylbutyl (E)-2-methyl-2-pentenoate (dominicalure-1), (S)(E)-11, an aggregation pheromone component for the lesser and the greater grain borers, has been efficiently synthesized from the main product of the palladium-catalyzed reaction between ethyl 2-pentynoate, 1a, and Bu3SnH, i.e. ethyl (E)-2-tributylstannyl-2-pentenoate, (E)-2a.

  DOI：

  10.1080/00397919308009761

文献信息

• Intermediates and methods of preparation of intermediates in the enantiomeric synthesis of (20R)homocamptothecins and the enantiomeric synthesis of (20R)homocamptothecins
  申请人：——

  公开号：US20030073840A1

  公开（公告）日：2003-04-17

  A method of synthesizing a compound having the formula: 1 from a compound having the formula: 2 wherein R 1 is hydrogen, fluorine, chlorine or SiR 5 R 6 R 7 , wherein R 5 , R 6 , and R 7 are independently the same or different an alkyl group or an aryl group, R 2 is an alkyl group, R 3 is a protecting group, R 4 is an alkyl group, an allyl group, a propargyl group —CO 2 H, or a benzyl group, R 8 is —CO 2 R 10 , wherein R 10 is an alkyl group or an aryl group, X 1 is OH and X 2 is H, includes the step of exposing compound (III) to at least one of an organic acid or an inorganic acid. A compound has the general formula (III).

  一种合成具有以下化学式的化合物的方法：1从具有以下化学式的化合物中进行：2其中R1为氢、氟、氯或SiR5R6R7，其中R5、R6和R7分别独立地为相同或不同的烷基基团或芳基基团，R2为烷基基团，R3为保护基团，R4为烷基基团、烯丙基团、丙炔基团、—CO2H或苄基团，R8为—CO2R10，其中R10为烷基基团或芳基基团，X1为OH，X2为H，包括将化合物(III)暴露于至少一种有机酸或无机酸中的步骤。化合物具有一般化学式(III)。
• Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans
  作者：Ana E Gabarda、Wu Du、Thomas Isarno、Raghuram S Tangirala、Dennis P Curran

  DOI：10.1016/s0040-4020(02)00632-4

  日期：2002.8

  An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents. (C) 2002 Published by Elsevier Science Ltd.
• Synthetic Applications of Alkyl (E)-2-Tributylstannyl-2-alkenoates: Selective Synthesis of (S)-1-Methylbutyl (E)-2-Methyl-2-pentenoate, an Aggregation Pheromone Component of<i>Rhyzopertha dominica</i>and<i>Prostephanus truncatus</i>
  作者：Renzo Rossi、Adriano Carpita、Paolo Cossi

  DOI：10.1080/00397919308009761

  日期：1993.1

  Stereoisomerically pure (S)-1-methylbutyl (E)-2-methyl-2-pentenoate (dominicalure-1), (S)(E)-11, an aggregation pheromone component for the lesser and the greater grain borers, has been efficiently synthesized from the main product of the palladium-catalyzed reaction between ethyl 2-pentynoate, 1a, and Bu3SnH, i.e. ethyl (E)-2-tributylstannyl-2-pentenoate, (E)-2a.