(Z)-3-Hydroxy-7-trimethylsilanyl-hept-5-enoic acid propyl ester | 142176-74-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (Z)-3-Hydroxy-7-trimethylsilanyl-hept-5-enoic acid propyl ester
• CAS: 142176-74-7
• 化学式: C₁₃H₂₆O₃Si
• 分子量: 258.433
• InChiKey: LSRYOVRARLAUFT-SREVYHEPSA-N

物化性质

• 沸点：
  331.1±42.0 °C(Predicted)
• 密度：
  0.943±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  17.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-Hydroxy-7-trimethylsilanyl-hept-5-enoic acid propyl ester 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 甲苯 为溶剂， 生成 3-Hydroxy-4-(3-trimethylsilanylmethyl-oxiranyl)-butyric acid propyl ester
  参考文献：
  名称：

  Stereoselective synthesis of syn-1,3-diols

  摘要：

  Z-allylsilanes 1 are epoxidized by V5+/TBHP with high erythro-selectivity (up to 97:3) . HF- or TBAF-induced fragmentation leads to syn-1,3-diols 3. Compound 3f can be transformed within two steps into a key synthon for the lactone moiety of compactin.

  DOI：

  10.1016/s0040-4039(00)92213-5
• 作为产物：
  描述：

  (S)-3-Hydroxy-7-trimethylsilanyl-hept-5-ynoic acid propyl ester 在 Lindlar's catalyst 氢气 作用下， 以 乙醇 为溶剂， 生成 (Z)-3-Hydroxy-7-trimethylsilanyl-hept-5-enoic acid propyl ester
  参考文献：
  名称：

  Stereoselective synthesis of syn-1,3-diols

  摘要：

  Z-allylsilanes 1 are epoxidized by V5+/TBHP with high erythro-selectivity (up to 97:3) . HF- or TBAF-induced fragmentation leads to syn-1,3-diols 3. Compound 3f can be transformed within two steps into a key synthon for the lactone moiety of compactin.

  DOI：

  10.1016/s0040-4039(00)92213-5

文献信息

• Stereoselective approach to trisubstituted tetrahydrofurans
  作者：Peter Mohr

  DOI：10.1016/s0040-4039(00)73723-3

  日期：1993.9

  Functionalized allylsilanes 1 undergo with acetals 2 under mild Broensted acid catalysis a transacetalization-ring closure reaction to afford in fair to good yield and high diastereoselectivity all-cis-tetrahydrofurans 3. The stereochemical outcome is independent of the double bond geometry.
• Hydroxyl-directed cyclopropanation of Z-allyl-silanes
  作者：Peter Mohr

  DOI：10.1016/0040-4039(95)01490-9

  日期：1995.10

  Z-5-Hydroxy-alk-2-enyl-silanes of general structure 1 are cyclopropanated by an excess of CH2I2/Et(2)n in good yield and excellent stereoselectivity. Ensuing protodesilylation, however, lacks efficient regiocontrol and affords syn-products 5 in modest yield bur high stereochemical purity.