(Z)-triethyl(1-iodohept-2-en-5-yn-3-yl)silane | 910224-38-3

• 英文名称: (Z)-triethyl(1-iodohept-2-en-5-yn-3-yl)silane
• 英文别名: triethyl-[(Z)-1-iodohept-2-en-5-yn-3-yl]silane
• CAS: 910224-38-3
• 化学式: C₁₃H₂₃ISi
• 分子量: 334.316
• InChiKey: XALZGNVEVBKFSW-QBFSEMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (Z)-triethyl(1-iodohept-2-en-5-yn-3-yl)silane 、 5-((triisopropylsilyl)oxy)pent-2-yn-1-ol 在 红铝 、 甲基锂 、 copper(l) chloride 作用下， 以 乙醚 、 甲苯 、 四氢呋喃 为溶剂， 反应 27.5h， 以70.9%的产率得到(2E,5E)-6-(triethylsilyl)-3-(2-(triisopropylsilyloxy)ethyl)deca-2,5-dien-8-yn-1-ol
  参考文献：
  名称：

  trans-Hydroalumination/Alkylation:  One-Pot Synthesis of Trisubstituted Allylic Alcohols

  摘要：

  Described herein is a method of stereoselective synthesis of trisubstituted allylic alcohols by alkylation of alkenyl alanates, formed in situ through treatment of propargyl alcohols with Vitride (Red-Al). This technique represents the first of its kind to feature a trans-hydrometalation, and is particularly effective for the formation of 1,4-dienes. Applications involving primary, secondary, and tertiary alcohols are discussed, as well as limitations regarding both alkyne and electrophile components.

  DOI：

  10.1021/ol0613721
• 作为产物：
  描述：

  (Z)-3-(triethylsilyl)hept-2-en-5-yn-1-ol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到(Z)-triethyl(1-iodohept-2-en-5-yn-3-yl)silane
  参考文献：
  名称：

  trans-Hydroalumination/Alkylation:  One-Pot Synthesis of Trisubstituted Allylic Alcohols

  摘要：

  Described herein is a method of stereoselective synthesis of trisubstituted allylic alcohols by alkylation of alkenyl alanates, formed in situ through treatment of propargyl alcohols with Vitride (Red-Al). This technique represents the first of its kind to feature a trans-hydrometalation, and is particularly effective for the formation of 1,4-dienes. Applications involving primary, secondary, and tertiary alcohols are discussed, as well as limitations regarding both alkyne and electrophile components.

  DOI：

  10.1021/ol0613721