t-butyl 2-acetyl-6-(t-butyldiphenylsilyloxy)hexanoate | 872530-18-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: t-butyl 2-acetyl-6-(t-butyldiphenylsilyloxy)hexanoate
• 英文别名: Tert-butyl 2-acetyl-6-[tert-butyl(diphenyl)silyl]oxyhexanoate；tert-butyl 2-acetyl-6-[tert-butyl(diphenyl)silyl]oxyhexanoate
• CAS: 872530-18-2
• 化学式: C₂₈H₄₀O₄Si
• 分子量: 468.709
• InChiKey: GHIRTFTVSMMOKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  t-butyl 2-acetyl-6-(t-butyldiphenylsilyloxy)hexanoate 在 氯化亚砜 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 7-(t-butyldiphenylsilyloxy)-3-chloroheptan-2-one
  参考文献：
  名称：

  A Triple Diene-Transmissive Diels−Alder Strategy To Build the Quassinoid Framework

  摘要：

  [GRAPHICS]An advanced intermediate to the highly oxygenated triterpene quassinoids was prepared in 14 steps from tetrahydrofuran. The key steps are three diene-transmissive Diels-Alder cycloadditions. Several features of this synthesis are noteworthy, including a successful Mitsunobu reaction on an allenylic alcohol, a rare [4 + 2] cycloaddition involving an enethiol ether dienophile, and complete control over all 10 chiral centers created.

  DOI：

  10.1021/ol0522236
• 作为产物：
  描述：

  乙酰乙酸叔丁酯 、 tert-butyl(4-iodobutoxy)diphenylsilane 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 60.0h， 以80%的产率得到t-butyl 2-acetyl-6-(t-butyldiphenylsilyloxy)hexanoate
  参考文献：
  名称：

  A Triple Diene-Transmissive Diels−Alder Strategy To Build the Quassinoid Framework

  摘要：

  [GRAPHICS]An advanced intermediate to the highly oxygenated triterpene quassinoids was prepared in 14 steps from tetrahydrofuran. The key steps are three diene-transmissive Diels-Alder cycloadditions. Several features of this synthesis are noteworthy, including a successful Mitsunobu reaction on an allenylic alcohol, a rare [4 + 2] cycloaddition involving an enethiol ether dienophile, and complete control over all 10 chiral centers created.

  DOI：

  10.1021/ol0522236

文献信息

• A Triple Diene-Transmissive Diels−Alder Strategy To Build the Quassinoid Framework
  作者：Amélie Dion、Pascal Dubé、Claude Spino

  DOI：10.1021/ol0522236

  日期：2005.12.1

  [GRAPHICS]An advanced intermediate to the highly oxygenated triterpene quassinoids was prepared in 14 steps from tetrahydrofuran. The key steps are three diene-transmissive Diels-Alder cycloadditions. Several features of this synthesis are noteworthy, including a successful Mitsunobu reaction on an allenylic alcohol, a rare [4 + 2] cycloaddition involving an enethiol ether dienophile, and complete control over all 10 chiral centers created.