methyl 5-(tert-butyldimethylsilyloxy)-4-hydroxypent-2-enoate | 950838-10-5

• 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: methyl 5-(tert-butyldimethylsilyloxy)-4-hydroxypent-2-enoate
• 英文别名: methyl (E,4S)-5-[tert-butyl(dimethyl)silyl]oxy-4-hydroxypent-2-enoate
• CAS: 950838-10-5
• 化学式: C₁₂H₂₄O₄Si
• 分子量: 260.406
• InChiKey: BCNNGCHDZHMYDJ-JARNTUPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-(tert-butyldimethylsilyloxy)-4-hydroxypent-2-enoate 、 反式-BETA-苯乙烯硼酸 在 di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium barium dihydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 以80%的产率得到
  参考文献：
  名称：

  Stereoselective Conjugate Addition of Aryl- and Alkenylboronic Acids to Acyclic γ,δ-Oxygen-Substituted α,β-Enoates

  摘要：

  The substrate-controlled Rh-I-catalyzed conjugate addition of aryl- and alkenylboronic acids to alpha,beta-unsaturated esters which bear gamma- and delta-oxygen substituents takes place in a highly anti diastereoselective fashion either when using gamma-hydroxyl unprotected starting materials or when the gamma-oxygen substituent is protected with a nonbulky group. The delta-oxygen substituent plays a role in the stereoselectivity of the reaction, and better results are obtained when this OH-group is protected.

  DOI：

  10.1021/ol7016033
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 methyl (4S)-4,5-dihydroxypent-2-enoate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以85%的产率得到methyl 5-(tert-butyldimethylsilyloxy)-4-hydroxypent-2-enoate
  参考文献：
  名称：

  Stereoselective Conjugate Addition of Aryl- and Alkenylboronic Acids to Acyclic γ,δ-Oxygen-Substituted α,β-Enoates

  摘要：

  The substrate-controlled Rh-I-catalyzed conjugate addition of aryl- and alkenylboronic acids to alpha,beta-unsaturated esters which bear gamma- and delta-oxygen substituents takes place in a highly anti diastereoselective fashion either when using gamma-hydroxyl unprotected starting materials or when the gamma-oxygen substituent is protected with a nonbulky group. The delta-oxygen substituent plays a role in the stereoselectivity of the reaction, and better results are obtained when this OH-group is protected.

  DOI：

  10.1021/ol7016033

文献信息

• Stereoselective Conjugate Addition of Aryl- and Alkenylboronic Acids to Acyclic γ,δ-Oxygen-Substituted α,β-Enoates
  作者：Amaya Segura、Aurelio G. Csákÿ

  DOI：10.1021/ol7016033

  日期：2007.8.1

  The substrate-controlled Rh-I-catalyzed conjugate addition of aryl- and alkenylboronic acids to alpha,beta-unsaturated esters which bear gamma- and delta-oxygen substituents takes place in a highly anti diastereoselective fashion either when using gamma-hydroxyl unprotected starting materials or when the gamma-oxygen substituent is protected with a nonbulky group. The delta-oxygen substituent plays a role in the stereoselectivity of the reaction, and better results are obtained when this OH-group is protected.