6-hydroxy-2,2-dimethyl-2-silatetralin | 156387-22-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-hydroxy-2,2-dimethyl-2-silatetralin
• 英文别名: 2,2-dimethyl-3,4-dihydro-1H-2-benzosilin-6-ol
• CAS: 156387-22-3
• 化学式: C₁₁H₁₆OSi
• 分子量: 192.333
• InChiKey: SEFFTKGWSSQTLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 6-hydroxy-2,2-dimethyl-2-silatetralin 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以63%的产率得到6-acetoxy-2,2-dimethyl-2-silatetralin
  参考文献：
  名称：

  Synthesis of 6-Acyl-2, 2-dimethyl-2-silatetralins

  摘要：

  Friedel-Crafts reaction of 2-silatetralin (4) with acid anhydrides (acetic anhydride, succinic anhydride, glutaric anhydride, phthalic anhydride, cis-1, 2-cyclohexanedicarboxylic an hydride, and diphenic anhydride) or benzoyl chloride in the presence of AICl(3) in CH2Cl2 at room temperature gave exclusively the corresponding 6-acyl-2-silatetralins in fair to good yield. This findings were supported by the MNDO molecular orbital calculations of 2-silatetralin (4).

  DOI：

  10.3987/com-95-7271
• 作为产物：
  描述：

  6-(3'-methoxycarbonylpropanoyl)-2,2-dimethyl-2-silatetralin 在 lithium aluminium tetrahydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 73.0h， 生成 6-hydroxy-2,2-dimethyl-2-silatetralin
  参考文献：
  名称：

  Synthesis of 6-Acyl-2, 2-dimethyl-2-silatetralins

  摘要：

  Friedel-Crafts reaction of 2-silatetralin (4) with acid anhydrides (acetic anhydride, succinic anhydride, glutaric anhydride, phthalic anhydride, cis-1, 2-cyclohexanedicarboxylic an hydride, and diphenic anhydride) or benzoyl chloride in the presence of AICl(3) in CH2Cl2 at room temperature gave exclusively the corresponding 6-acyl-2-silatetralins in fair to good yield. This findings were supported by the MNDO molecular orbital calculations of 2-silatetralin (4).

  DOI：

  10.3987/com-95-7271

文献信息

• Synthesis of 2-Silatetralin Derivatives Bearing Oxygen Functional Groups
  作者：Osamu Hoshino、Akihisa Hirokawa、Toru Taguchi、Kenji Miyauchi

  DOI：10.3987/com-93-6659

  日期：——

  The Grignard reagents of methoxy- or methylene-dioxyphenylmethyl chlorides (12a-e) were treated with trichloro-vinylsilane in THF or ether to give methoxy- or methylenedioxy-benzyldichlorovinylsilanes (13a-e). The reaction of 13a-d in the presence of AlCl3 in CS2 or CH2Cl2 followed by treatment with MeOH and cyclohexylamine or Et3N afforded methoxy-2-silatetralins (16a-d). Treatment of 16a-d with MeMgl or EtMgBr in ether gave the corresponding 2,2-dimethyl- or 2,2-diethyl-2-silatetralins (17a-d or 18). Demethylation of 17a, 17b or 18 with BBr3 in CH2Cl2 furnished hydroxy-2-silatetralins (19a, 19b or 20).