Tert-butyl-dimethyl-[(5-trimethylsilylfuran-3-yl)methoxy]silane | 89861-08-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: Tert-butyl-dimethyl-[(5-trimethylsilylfuran-3-yl)methoxy]silane
• CAS: 89861-08-5
• 化学式: C₁₄H₂₈O₂Si₂
• 分子量: 284.546
• InChiKey: WHEWQMQIOWGUIS-UHFFFAOYSA-N

物化性质

• 沸点：
  286.1±25.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Tert-butyl-dimethyl-[(5-trimethylsilylfuran-3-yl)methoxy]silane 在 过氧乙酸 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以75%的产率得到4-<<(tert-butyl)dimethylsiloxy>methyl>furan-2(5H)-one
  参考文献：
  名称：

  3-Alkylfurans as useful synthetic equivalents for substituted δ2-butenolides

  摘要：

  DOI：

  10.1016/s0040-4039(00)94214-x
• 作为产物：
  描述：

  3-呋喃甲醇 以37%的产率得到Tert-butyl-dimethyl-[(5-trimethylsilylfuran-3-yl)methoxy]silane
  参考文献：
  名称：

  γ-羟基丁烯内酯的区域特异性合成。取代的2-三甲基甲硅烷基呋喃的光敏氧化

  摘要：

  通过对2-三甲基甲硅烷基-呋喃衍生物进行光敏氧化来完成取代的γ-羟基丁烯内酯的区域特异性合成，并且还实现了在侧链具有三和四取代的烯烃的呋喃环的化学选择性氧化。

  DOI：

  10.1016/s0040-4039(00)98769-0

文献信息

• Regiospecific synthesis of γ-hydroxybutenolide. Photosensitized oxygenation of substituted 2-trimethylsilylfuran
  作者：Shigeo Katsumura、Keiko Hori、Shinya Fujiwara、Sachihiko Isoe

  DOI：10.1016/s0040-4039(00)98769-0

  日期：——

  Regiospecific synthesis of substituted γ-hydroxybutenolide was accomplished by photosensitized oxygenation of 2-trimethylsilyl-furan derivatives, and chemoselective oxidation of furan ring having tri- and tetra-substituted olefins in the side chain was also achieved.

  通过对2-三甲基甲硅烷基-呋喃衍生物进行光敏氧化来完成取代的γ-羟基丁烯内酯的区域特异性合成，并且还实现了在侧链具有三和四取代的烯烃的呋喃环的化学选择性氧化。
• GOLDSMITH, D.;LIOTTA, D.;SAINDANE, M.;WAYKOLE, L.;BOWEN, P., TETRAHEDRON LETT., 1983, 24, N 52, 5835-5838
  作者：GOLDSMITH, D.、LIOTTA, D.、SAINDANE, M.、WAYKOLE, L.、BOWEN, P.

  DOI：——

  日期：——
• BURES, EDWARD J.;KEAY, BRIAN A., TETRAHEDRON LETT., 28,(1987) N 48, 5965-5968
  作者：BURES, EDWARD J.、KEAY, BRIAN A.

  DOI：——

  日期：——
• Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 1. [1,4] O → C and [1,4] C → O Silyl Migrations of Silyl Ethers and Esters Attached to Furan and Thiophene Rings
  作者：Edward Bures、Patrick G. Spinazzé,、Giovanna Beese、Ian R. Hunt、Christine Rogers、Brian A. Keay

  DOI：10.1021/jo971097j

  日期：1997.12.1

  [1,4] O --> C and [1,4] C --> O rearrangements are described for a variety of furans and thiophenes. Treatment of 3-((silyloxy)methyl)furans and -thiophenes with n-BuLi in HMPA provided 2-silylated-3-(hydroxymethyl)furans and -thiophenes in good to excellent yields. The reaction was shown by crossover studies to proceed via an intramolecular [1,4] O --> C silyl migration. Silyl esters of 3-furoic acids also underwent an intramolecular [1,4] O --> C silyl migration to provide 2-silylated-3-furoic acids in moderate to good yield when treated with a mixture of LDA and HMPA. Finally, the above silyl migrations were shown to be reversible. Treatment of 2-silylated-3-(hydroxymethyl)furans and -thiophenes with NaH in DMF provided 3-((silyloxy)methyl)furans and -thiophenes in excellent yields via a [1,4] C --> O silyl migration. The [1,4] C --> O silyl migration was also shown to be an intramolecular process by a crossover study.
• 3-Alkylfurans as useful synthetic equivalents for substituted δ2-butenolides
  作者：David Goldsmith、Dennis Liotta、Manohar Saindane、Liladhar Waykole、Phillip Bowen

  DOI：10.1016/s0040-4039(00)94214-x

  日期：1983.1