(cis)-1-benzyloxy-4-(tert-butyldimethyl)silyloxy-2-butene | 128741-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (cis)-1-benzyloxy-4-(tert-butyldimethyl)silyloxy-2-butene
• 英文别名: tert-butyl-dimethyl-[(Z)-4-phenylmethoxybut-2-enoxy]silane
• CAS: 128741-83-3
• 化学式: C₁₇H₂₈O₂Si
• 分子量: 292.494
• InChiKey: ODRAJAVKOVULMH-KTKRTIGZSA-N

物化性质

• 沸点：
  340.4±30.0 °C(Predicted)
• 密度：
  0.934±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (cis)-1-benzyloxy-4-(tert-butyldimethyl)silyloxy-2-butene 在 cerium(III) chloride 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 4.5h， 以95%的产率得到顺-4-苄氧基-2-丁烯-1-醇
  参考文献：
  名称：

  A Mild, Efficient, and Selective Method for the Desilylation of More Common Trialkylsilyl Ethers by Cerium(III) Chloride Heptahydrate and Sodium Iodide in Acetonitrile

  摘要：

  三烷基硅醚在乙腈中与七水合氯化铈和碘化钠反应，提供了一个简单、方便且化学选择性的脱硅基化过程，并且母体醇以高产率获得。在乙酸酯、苄基醚和四氢吡喃醚存在下，三烷基硅醚选择性地断裂。

  DOI：

  10.1055/s-1998-1601
• 作为产物：
  描述：

  1-O-tert-butyldimethylsilyl-2-O-methanesulfonyloxy-ethane 在 ammonium heptamolybdate 双氧水 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 28.5h， 生成 (cis)-1-benzyloxy-4-(tert-butyldimethyl)silyloxy-2-butene
  参考文献：
  名称：

  烯丙基醚和醇的高效和立体选择性合成。

  摘要：

  [结构：见正文]基于独特的Kocienski-Julia烯化反应，开发了一种短而有效的烯丙基TBS醚和烯丙基醇的合成方法。获得烯丙基醇和烯丙基醚的产率高至优异，并且具有高（E）-选择性。条件温和，程序可广泛应用。

  DOI：

  10.1021/ol062433y

文献信息

• Regiochemical control of the ring opening of 1:2-epoxides by means of chelating processes. 10. Synthesis and ring opening reactions of mono- and difunctionalized cis and trans aliphatic oxirane systems
  作者：Francesca Azzena、Federico Calvani、Paolo Crotti、Cristina Gardelli、Franco Macchia、Mauro Pineschi

  DOI：10.1016/0040-4020(95)00633-j

  日期：1995.9

  The regiochemical outcome of the ring opening of 1:2-epoxides through chelation processes assisted by metal ions, was verified in mono- and difunctionalized aliphatic oxirane systems bearing the heterofunctionality (OR) in an homoallylic and/or allylic relationship to the oxirane ring. The effect of the distance of the OR functionality from the oxirane ring and of the type of protective group on the

  通过单官能和双官能的脂族环氧乙烷体系在与环氧乙烷环呈均烯丙基和/或烯丙基关系的杂官能度（OR）中验证了通过金属离子辅助的螯合过程使1：2-环氧化物开环的区域化学结果。检查了OR官能团与环氧乙烷环的距离以及保护基类型对这些系统的区域化学结果的影响。在某些情况下，使用LiClO 4或Mg（ClO 4）2作为促进金属盐使得有可能获得良好的区域交替方法。
• Synthesis of New Nucleoside Analogues Comprising a Geminal Difluorocyclopropane Moiety as Potential Antiviral/Antitumor Agents
  作者：Yao-Ling Qiu、Jiri Zemlicka

  DOI：10.1080/07328319908044881

  日期：1999.10

  Geminal difluorocyclopropane analogues of nucleosides 7a - 7e were synthesized. Compounds 7a and 7c - 7e were obtained by alkylation of nucleic acid bases or their appropriate precursors with (cis)-1-benzyloxymethyl-2-bromomethyl-3,3-difluorocyclopropane (8). Analogue 7b was prepared by hydrolysis of 2-amino-6-chloropurine derivative 7e. Compounds 7a - 7d did not exhibit any antiviral activity against HCMV, HSV-1, HSV-2 EBV, VZV, HBV and HIV-1 or antitumor effects against murine leukemia L1210, mouse tumors PO3 or C38 and human tumor H15.
• Preparation of methylene-gem-difluorocyclopropanes and its reactivity as Michael acceptor
  作者：Takeo Taguchi、Masahito Kurishita、Akira Shibuya、Kifune Aso

  DOI：10.1016/s0040-4020(97)00613-3

  日期：1997.7

  Preparation of methylene-gem-difluorocyclopropanes 3 was achieved through the selenoxide elimination reaction derived from gem-difluorocyclopropylmethanols 1, while this method can not be applied to non-fluorinated cyclopropylmethanols. The methylene-gem-difluorocyclopropane 3 showed a high reactivity as a Michael acceptor in the reaction with thiol or amine. (C) 1997 Elsevier Science Ltd.
• Efficient and Stereoselective Synthesis of Allylic Ethers and Alcohols
  作者：Jiří Pospíšil、István E. Markó

  DOI：10.1021/ol062433y

  日期：2006.12.1

  [Structure: see text] A short and efficient synthesis of allylic TBS ethers and allylic alcohols has been developed, based upon a unique Kocienski-Julia olefination reaction. Allylic alcohols and allylic ethers are obtained in good to excellent yields and with high (E)-selectivity. The conditions are mild and the procedure is broadly applicable.

  [结构：见正文]基于独特的Kocienski-Julia烯化反应，开发了一种短而有效的烯丙基TBS醚和烯丙基醇的合成方法。获得烯丙基醇和烯丙基醚的产率高至优异，并且具有高（E）-选择性。条件温和，程序可广泛应用。
• A Mild, Efficient, and Selective Method for the Desilylation of More Common Trialkylsilyl Ethers by Cerium(III) Chloride Heptahydrate and Sodium Iodide in Acetonitrile
  作者：Giuseppe Bartoli、Marcella Bosco、Enrico Marcantoni、Letizia Sambri、Elisabetta Torregiani

  DOI：10.1055/s-1998-1601

  日期：1998.2

  Treatment of trialkylsilyl ethers with cerium(III) chloride heptahydrate and sodium iodide in acetonitrile provides a simple, convenient, and chemoselective process for desilylation, and the parent alcohol was obtained in high yield. The trialkylsilyl ethers have been cleaved selectively in the presence of acetate, benzyl and tetrahydropyranyl ethers.

  三烷基硅醚在乙腈中与七水合氯化铈和碘化钠反应，提供了一个简单、方便且化学选择性的脱硅基化过程，并且母体醇以高产率获得。在乙酸酯、苄基醚和四氢吡喃醚存在下，三烷基硅醚选择性地断裂。