tert-butyl (furan-3-ylmethoxy)dimethylsilane | 89861-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: tert-butyl (furan-3-ylmethoxy)dimethylsilane
• 英文别名: Silane, (1,1-dimethylethyl)(3-furanylmethoxy)dimethyl-；tert-butyl-(furan-3-ylmethoxy)-dimethylsilane
• CAS: 89861-06-3
• 化学式: C₁₁H₂₀O₂Si
• 分子量: 212.364
• InChiKey: JXLODBQIKOKJRE-UHFFFAOYSA-N

物化性质

• 沸点：
  106-109 °C(Press: 20 Torr)
• 密度：
  0.924±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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 (furan-3-ylmethoxy)dimethylsilane 在 正丁基锂 作用下， 以 六甲基磷酰三胺 、 乙二醇二甲醚 为溶剂， 反应 0.02h， 以88%的产率得到3-呋喃甲醇,2-[(1,1-二甲基乙基)二甲基甲硅烷基]-
  参考文献：
  名称：

  通过呋喃的区域选择性锂化和 α-甲硅烷基呋喃的光敏氧化合成四取代丁烯内酯，溴贝克瑞德

  摘要：

  四取代的卤代丁烯内酯溴贝克瑞德的直接合成是通过三取代的α-三烷基甲硅烷基呋喃的光敏氧化来实现的，该三取代的α-三烷基甲硅烷基呋喃是通过区域选择性锂化将所需的取代基引入呋喃环中获得的。

  DOI：

  10.1246/cl.1993.1525
• 作为产物：
  描述：

  3-呋喃甲醇 在 正丁基锂 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 tert-butyl (furan-3-ylmethoxy)dimethylsilane
  参考文献：
  名称：

  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

  摘要：

  [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.

  DOI：

  10.1021/jo971097j

文献信息

• [EN] HETEROARYL COMPOUNDS USEFUL AS INHIBITORS OF SUMO ACTIVATING ENZYME<br/>[FR] COMPOSÉS HÉTÉROARYLE UTILES EN TANT QU'INHIBITEURS DE L'ENZYME D'ACTIVATION SUMO
  申请人：DUFFEY MATTHEW O

  公开号：WO2016004136A1

  公开（公告）日：2016-01-07

  Disclosed are chemical entities which are compounds of formula (I); or pharmaceutically acceptable salts thereof; wherein Y, Ra, Ra', Rb, Rc, X1, X2, X3, Rd, Z1, and Z2 have the values described herein and stereochemical configurations depicted at asterisked positions indicate absolute stereochemistry. Chemical entities according to the disclosure can be useful as inhibitors of Sumo Activating Enzyme (SAE). Further provided are pharmaceutical compositions comprising a compound of the disclosure and methods of using the compositions in the treatment of proliferative, inflammatory, cardiovascular, and neurodegenerative diseases or disorders.

  公开了公式(I)的化合物或其药物可接受的盐； 其中Y、Ra、Ra'、Rb、Rc、X1、X2、X3、Rd、Z1和Z2具有本文所述的值，并且星号位置表示的立体化学配置指示绝对立体化学。 根据本公开的化学实体可用作Sumo激活酶（SAE）的抑制剂。 进一步提供了包含本公开化合物的药物组合物以及使用该组合物治疗增殖性、炎症性、心血管和神经退行性疾病或病症的方法。
• Synthesis of a Functionalized Oxabicyclo[2.2.1]-Heptene-Based Chemical Library
  作者：Sarah B. Luesse、Gregg Wells、Jeanne Miller、Erin Bolstad、Stephen C. Bergmeier、Mark C. McMills、Nigel D. Priestley、Dennis L. Wright

  DOI：10.2174/138620712798280835

  日期：2012.1.1

  The 7-oxabicyclo[2.2.1]heptene ring system is a common structural motif in many pharmacologically interesting molecules. We recognized the potential to employ this highly oxygenated and conformationally-restricted scaffold in diversity-oriented synthesis to generate a library of non-chiral but topologically complex compounds. Herein, we report the synthesis and biological evaluation of two 96-member tricyclic libraries containing the oxabicyclo[2.2.1]heptene framework using acetal formation as the key step.

  7-氧杂双环[2.2.1]庚烯环系统是许多具有药理学意义分子中的常见结构基元。我们认识到，可以通过利用这种高度氧化的、构象受限的骨架，在定向多样性合成中生成一组非手性但拓扑结构复杂的化合物。本文中，我们报道了利用缩醛化反应作为关键步骤，合成并生物评估了两个包含96个成员的三环化合物库，这两个库均含有氧杂双环[2.2.1]庚烯框架。
• Remote Enantioselective Friedel-Crafts Alkylations of Furans through HOMO Activation
  作者：Jun-Long Li、Cai-Zhen Yue、Peng-Qiao Chen、You-Cai Xiao、Ying-Chun Chen

  DOI：10.1002/anie.201403082

  日期：2014.5.19

  Catalytic asymmetric Friedel–Crafts alkylation is a powerful protocol for constructing a chiral C(sp2)C(sp3) bond. Most previous examples rely on LUMO activation of the electrophiles using chiral catalysts with subsequent attack by electron‐rich arenes. Presented herein is an alternative strategy in which the HOMO of the aromatic π system of 2‐furfuryl ketones is raised through the formation of a formal

  催化不对称Friedel-Crafts烷基化反应是构建手性C（sp 2）C（sp 3）键的强大方法。以前的大多数示例都依赖于使用手性催化剂的亲电子的LUMO活化，随后又被富电子芳烃攻击。本文提出了一种替代策略，其中通过使用手性伯胺形成正式的三烯胺物种，提高了2-糠基酮的芳族π系统的HOMO。亚烷基丙二腈在5位发生独家区域选择性烷基化，并且通过这种远程活化获得了高反应活性和出色的对映选择性（高达95％ee）。
• Rhodium- and Platinum-Catalyzed [4+3] Cycloaddition with Concomitant Indole Annulation: Synthesis of Cyclohepta[<i>b</i>]indoles
  作者：Dongxu Shu、Wangze Song、Xiaoxun Li、Weiping Tang

  DOI：10.1002/anie.201209266

  日期：2013.3.11

  Various substituted cyclohepta[b]indoles were prepared from propargylic ethers and dienes by a tandem indole annulation/[4+3] cycloaddition (see scheme; Boc=tert‐butoxycarbonyl). Both acyclic and cyclic dienes participated in the [4+3] cycloaddition to afford tri‐ and tetracyclic products, respectively. Electron‐deficient phosphine or phosphite ligands facilitated the tandem reaction.

  通过串联吲哚环化/[4+3]环加成反应，由炔丙醚和二烯制备了各种取代的环庚[ b ]吲哚（参见方案；Boc=叔丁氧基羰基）。无环和环状二烯都参与[4+3]环加成反应，分别生成三环和四环产物。缺电子膦或亚磷酸酯配体促进了串联反应。
• Synthesis of Tetrasubstituted Butenolide, Bromobeckerelide, by Regioselective Lithiation of Furan Followed by Photosensitized Oxygenation of α-Silylfuran
  作者：Shigeo Katsumura、Koji Ichikawa、Hajime Mori

  DOI：10.1246/cl.1993.1525

  日期：1993.9

  A straightforward synthesis of a tetrasubstituted halobutenolide, bromobeckerelide, was achieved by photosensitized oxygenation of a trisubstituted α-trialkylsilylfuran which was obtained by the introduction of desired substituents into a furan ring via regioselective lithiation.

  四取代的卤代丁烯内酯溴贝克瑞德的直接合成是通过三取代的α-三烷基甲硅烷基呋喃的光敏氧化来实现的，该三取代的α-三烷基甲硅烷基呋喃是通过区域选择性锂化将所需的取代基引入呋喃环中获得的。