(S)-(E)-(-)-1-(Tributylstannyl)-1-undecen-3-ol | 149655-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(E)-(-)-1-(Tributylstannyl)-1-undecen-3-ol
• 英文别名: (R)-n-C8H17CH(OH)CHCHSnBu3
• CAS: 149655-17-4；157088-33-0
• 化学式: C₂₃H₄₈OSn
• 分子量: 459.344
• InChiKey: UBSFCGVWNPOMQC-LOSFGHDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.04
• 重原子数：
  25
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-碘尿嘧啶 、 (S)-(E)-(-)-1-(Tributylstannyl)-1-undecen-3-ol 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 三(2-呋喃基)膦 作用下， 以 various solvent(s) 为溶剂， 反应 48.0h， 以65%的产率得到5-(3'-Hydroxy-1'-undecenyl)uracil
  参考文献：
  名称：

  Catalytic Asymmetric Addition of Polyfunctional Dialkylzincs to .beta.-Stannylated and .beta.-Silylated Unsaturated Aldehydes

  摘要：

  The addition of functionalized dialkylzincs to readily available beta-stannylated or beta-silylated unsaturated aldehydes in the presence of a catalytic amount of (1R,2R)-1,2-bis(trifluorosulfonamido)cyclohexane (8 mol%) provides chiral allylic alcohols in good yields (60-90%) and excellent enantioselectivity (usually in the range of 85-95% ee). The synthetic utility of these allylic alcohols as chiral building blacks is demonstrated. The gamma-stannylated allylic alcohols were submitted to a Stille coupling leading to polyfunctional allylic alcohols and gamma-alkoxy enones. A treatment with CuCN in N-methylpyrrolidone at 130 degrees C provided chiral unsaturated gamma-hydroxy nitriles. Finally, the desilylation of the gamma-silylated alcohols gave chiral allylic alcohols having a terminal double bond. The catalytic asymmetric addition was found to show an important inverse temperature dependance. A mechanism for this addition is proposed.

  DOI：

  10.1021/jo00094a027
• 作为产物：
  描述：

  (E)-3-(tributylstannyl)acrylaldehyde 、 dioctylzinc 在 {Ti(OiPr)2((1R,2R)-1,2-bis(trifluorosulfonamido)cyclohexane)} 作用下， 以 甲苯 为溶剂， 以72%的产率得到(S)-(E)-(-)-1-(Tributylstannyl)-1-undecen-3-ol
  参考文献：
  名称：

  Brieden, Walter; Ostwald, Roswitha; Knochel, Paul, Angewandte Chemie, 1993, vol. 105, # 4, p. 629 - 631

  摘要：

  DOI：

文献信息

• Simple Preparation of the Optically Active γ-Hydroxy Vinylstannanes Using Lipase-Catalyzed Hydrolysis
  作者：Toshiyuki Itoh、Tadataka Ohta

  DOI：10.1246/cl.1991.217

  日期：1991.2

  An efficient optical resolution of γ-hydroxy vinylstannanes was achieved by the lipase-catalyzed enantioselective hydrolysis of the corresponding racemic acetates using lipase PS(Pseudomonas sp.).

  通过使用脂肪酶 PS（假单胞菌属）对相应的外消旋乙酸酯进行脂肪酶催化的对映选择性水解，实现了 γ-羟基乙烯基锡烷的有效光学拆分。
• Ostwald Roswitha, Chavant Pierre-Yves, Stadtmueller Heinz, Knochel Paul, J. Org. Chem., 59 (1994) N 15, S 4143-4153
  作者：Ostwald Roswitha, Chavant Pierre-Yves, Stadtmueller Heinz, Knochel Paul

  DOI：——

  日期：——
• Brieden, Walter; Ostwald, Roswitha; Knochel, Paul, Angewandte Chemie, 1993, vol. 105, # 4, p. 629 - 631
  作者：Brieden, Walter、Ostwald, Roswitha、Knochel, Paul

  DOI：——

  日期：——
• Catalytic Asymmetric Addition of Polyfunctional Dialkylzincs to .beta.-Stannylated and .beta.-Silylated Unsaturated Aldehydes
  作者：Roswitha Ostwald、Pierre-Yves Chavant、Heinz Stadtmueller、Paul Knochel

  DOI：10.1021/jo00094a027

  日期：1994.7

  The addition of functionalized dialkylzincs to readily available beta-stannylated or beta-silylated unsaturated aldehydes in the presence of a catalytic amount of (1R,2R)-1,2-bis(trifluorosulfonamido)cyclohexane (8 mol%) provides chiral allylic alcohols in good yields (60-90%) and excellent enantioselectivity (usually in the range of 85-95% ee). The synthetic utility of these allylic alcohols as chiral building blacks is demonstrated. The gamma-stannylated allylic alcohols were submitted to a Stille coupling leading to polyfunctional allylic alcohols and gamma-alkoxy enones. A treatment with CuCN in N-methylpyrrolidone at 130 degrees C provided chiral unsaturated gamma-hydroxy nitriles. Finally, the desilylation of the gamma-silylated alcohols gave chiral allylic alcohols having a terminal double bond. The catalytic asymmetric addition was found to show an important inverse temperature dependance. A mechanism for this addition is proposed.