(S)-(E)-5-Phenyl-1-(triisopropylsiloxy)-1-penten-5-ol | 165277-23-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(E)-5-Phenyl-1-(triisopropylsiloxy)-1-penten-5-ol
• 英文别名: (E,1S)-1-phenyl-5-tri(propan-2-yl)silyloxypent-4-en-1-ol
• CAS: 165277-23-6
• 化学式: C₂₀H₃₄O₂Si
• 分子量: 334.574
• InChiKey: GFDBVSUDPWHHJC-RNTFSAEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(E)-5-Phenyl-1-(triisopropylsiloxy)-1-penten-5-ol 在 碘 、 potassium carbonate 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以78%的产率得到3-Iodo-6(S)-phenyl-2-(triisopropylsiloxy)tetrahydropyran
  参考文献：
  名称：

  Preparation and Reactions of Diorganozincs from Dienic Silyl Enol Ethers

  摘要：

  The hydroboration of the dienic silyl enol ethers 1a-d with Et(2)BH produces organoboranes which are readily converted under mild conditions by a treatment with Et(2)Zn to the corresponding dialkylzincs 2a-d. These organometallics react after transmetalation with CuCN . 2LiCl with various electrophiles affording polyfunctional silyl enol ethers of type 4. In the presence of the chiral catalyst (1R,2R)-bis(trifluoromethanesulfonamido)cyclohexane 6, the dialkylzinc 2b was added to various aldehydes leading to hydroxy silyl enol ethers of type 8 in satisfactory yields (45-77%) and excellent enantioselectivities (85 to >96 % ee). The chiral products 8 can be oxidatively cyclized using t-BuOOH and catalytic amounts of VO(acac)(2) furnishing trisubstituted tetrahydropyrans like 9a,b with high diastereoselectivity. An iodoalkoxylation of 8 affords after HI elimination and Jones oxidation the unsaturated valerolactone 13.

  DOI：

  10.1021/jo00116a013
• 作为产物：
  描述：

  苯甲醛 、 (E)-1-(triisopropylsilyloxy)-1,3-butadiene 生成 (S)-(E)-5-Phenyl-1-(triisopropylsiloxy)-1-penten-5-ol
  参考文献：
  名称：

  Preparation and Reactions of Diorganozincs from Dienic Silyl Enol Ethers

  摘要：

  The hydroboration of the dienic silyl enol ethers 1a-d with Et(2)BH produces organoboranes which are readily converted under mild conditions by a treatment with Et(2)Zn to the corresponding dialkylzincs 2a-d. These organometallics react after transmetalation with CuCN . 2LiCl with various electrophiles affording polyfunctional silyl enol ethers of type 4. In the presence of the chiral catalyst (1R,2R)-bis(trifluoromethanesulfonamido)cyclohexane 6, the dialkylzinc 2b was added to various aldehydes leading to hydroxy silyl enol ethers of type 8 in satisfactory yields (45-77%) and excellent enantioselectivities (85 to >96 % ee). The chiral products 8 can be oxidatively cyclized using t-BuOOH and catalytic amounts of VO(acac)(2) furnishing trisubstituted tetrahydropyrans like 9a,b with high diastereoselectivity. An iodoalkoxylation of 8 affords after HI elimination and Jones oxidation the unsaturated valerolactone 13.

  DOI：

  10.1021/jo00116a013

文献信息

• Preparation and Reactions of Diorganozincs from Dienic Silyl Enol Ethers
  作者：A. Devasagayaraj、L. Schwink、P. Knochel

  DOI：10.1021/jo00116a013

  日期：1995.6

  The hydroboration of the dienic silyl enol ethers 1a-d with Et(2)BH produces organoboranes which are readily converted under mild conditions by a treatment with Et(2)Zn to the corresponding dialkylzincs 2a-d. These organometallics react after transmetalation with CuCN . 2LiCl with various electrophiles affording polyfunctional silyl enol ethers of type 4. In the presence of the chiral catalyst (1R,2R)-bis(trifluoromethanesulfonamido)cyclohexane 6, the dialkylzinc 2b was added to various aldehydes leading to hydroxy silyl enol ethers of type 8 in satisfactory yields (45-77%) and excellent enantioselectivities (85 to >96 % ee). The chiral products 8 can be oxidatively cyclized using t-BuOOH and catalytic amounts of VO(acac)(2) furnishing trisubstituted tetrahydropyrans like 9a,b with high diastereoselectivity. An iodoalkoxylation of 8 affords after HI elimination and Jones oxidation the unsaturated valerolactone 13.