1-(tert-butyldimethylsilyl)-4-iodoindole | 211295-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(tert-butyldimethylsilyl)-4-iodoindole
• 英文别名: Tert-butyl-(4-iodoindol-1-yl)-dimethylsilane
• CAS: 211295-26-0
• 化学式: C₁₄H₂₀INSi
• 分子量: 357.31
• InChiKey: OSLJNBCTBLQPBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(tert-butyldimethylsilyl)-4-iodoindole 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以75%的产率得到4-碘-1H-吲哚
  参考文献：
  名称：

  Nickel-Mediated Inter- and Intramolecular C–S Coupling of Thiols and Thioacetates with Aryl Iodides at Room Temperature

  摘要：

  A Ni(0)-catalyzed intermolecular cross-coupling of various functionalized thiols and aryl Iodides has been developed and successfully extended to less explored intramolecular versions, where thioacetates could also be utilized as the strategic surrogate. Air-stable precatalysts, very mild conditions, and an easy protocol allow rapid access to medicinally useful aryl thioethers, as demonstrated in the facile synthesis of (+/-)-chuangxinmycin as a key step.

  DOI：

  10.1021/ol303366u
• 作为产物：
  描述：

  4-溴-1-(叔丁基二甲基硅基)吲哚 在 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以89%的产率得到1-(tert-butyldimethylsilyl)-4-iodoindole
  参考文献：
  名称：

  Nickel-Mediated Inter- and Intramolecular C–S Coupling of Thiols and Thioacetates with Aryl Iodides at Room Temperature

  摘要：

  A Ni(0)-catalyzed intermolecular cross-coupling of various functionalized thiols and aryl Iodides has been developed and successfully extended to less explored intramolecular versions, where thioacetates could also be utilized as the strategic surrogate. Air-stable precatalysts, very mild conditions, and an easy protocol allow rapid access to medicinally useful aryl thioethers, as demonstrated in the facile synthesis of (+/-)-chuangxinmycin as a key step.

  DOI：

  10.1021/ol303366u

文献信息

• A Synthesis of Arcyriacyanin A, an Unsymmetrically Substituted Indole Pigment of the Slime Mould by Palladium Catalyzed Cross-Coupling Reaction.
  作者：Masayuki MURASE、Kazuhiro WATANABE、Takayuki KURIHARA、Seisho TOBINAGA

  DOI：10.1248/cpb.46.889

  日期：——

  The slime mould alkaloid of Arcyria obvelata Onsberg, arcyriacyanin A, was synthesized by the palladium catalyzed cross-coupling reaction with the indolylborate and 4-iodoindole derivatives, which provides an unsymmetrically substituted indole pigment.

  通过钯催化与吲哚硼酸酯和 4-碘吲哚衍生物的交叉偶联反应，合成了 Arcyria obvelata Onsberg 的粘菌生物碱 arcyriacyanin A，从而提供了一种不对称取代的吲哚色素。
• Nickel-Mediated Inter- and Intramolecular C–S Coupling of Thiols and Thioacetates with Aryl Iodides at Room Temperature
  作者：Xiao-Bo Xu、Jian Liu、Jian-Jian Zhang、Ya-Wen Wang、Yu Peng

  DOI：10.1021/ol303366u

  日期：2013.2.1

  A Ni(0)-catalyzed intermolecular cross-coupling of various functionalized thiols and aryl Iodides has been developed and successfully extended to less explored intramolecular versions, where thioacetates could also be utilized as the strategic surrogate. Air-stable precatalysts, very mild conditions, and an easy protocol allow rapid access to medicinally useful aryl thioethers, as demonstrated in the facile synthesis of (+/-)-chuangxinmycin as a key step.