4-苄氧基-2-甲基戊-2-烯 | 74262-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-苄氧基-2-甲基戊-2-烯
• 英文名称: 4-benzyloxy-2-methylpent-2-ene
• 英文别名: 4-Methylpent-3-en-2-yloxymethylbenzene
• CAS: 74262-58-1
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: AXUMUCUDEXDAGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-苄氧基-2-甲基戊-2-烯 以35%的产率得到
  参考文献：
  名称：

  HEATHCOCK C. H.; YOUNG S. D.; HAGEN J. P.; PIRRING M. C.; WHITE C. T.; VA+, J. ORG. CHEM., 1980, 45, NO 19, 3846-3856

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基-3-戊醇 、 溴甲苯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到4-苄氧基-2-甲基戊-2-烯
  参考文献：
  名称：

  烯丙基醚的金属催化亚甲硅烷插入：手性烯丙基硅烷的立体选择性形成

  摘要：

  亚甲硅烷插入烯丙基醚发生在表面上以提供对映体富集的烯丙基硅烷和乙硅烷。利用银和铜介导的条件将亚甲硅烷插入各种受保护的烯丙醇被证明是形成烯丙硅烷的通用方法。烯丙基乙硅烷的反应与烯丙基硅烷类似，同时发生环化和烯丙基化反应。

  DOI：

  10.1021/ja073758s

文献信息

• Acyclic stereoselection. 9. Stereochemistry of the addition of lithium enolates to .alpha.-alkoxy aldehydes
  作者：Clayton H. Heathcock、Steven D. Young、James P. Hagen、Michael C. Pirrung、Charles T. White、Don VanDerveer

  DOI：10.1021/jo01307a023

  日期：1980.9
• Regio- and Stereochemistry on the Electrophilic Trapping of Allylic Samariums Generated by Reductive Cleavage of Allylic Ethers with (C₅Me₅)₂Sm(thf)_<i>n</i>
  作者：Ken Takaki、Takeshi Kusudo、Shinya Uebori、Tetsushi Nishiyama、Tohru Kamata、Masaki Yokoyama、Katsuomi Takehira、Yoshikazu Makioka、Yuzo Fujiwara

  DOI：10.1021/jo9723016

  日期：1998.6.1

  The C-O bond of allylic benzyl ethers was selectively cleaved with Cp-2*Sm(thf)(n) to give allylic samarium complexes in good yields. Facility of their bond fission has been found to be comparable to that of the corresponding propargylic ethers intermolecularly, but lower intramolecularly. Regio- and stereochemistry on the electrophilic trapping of the allylic complexes thus generated remarkably depended on the nature of the electrophiles. They reacted with carbonyl compounds exclusively from the most substituted terminus of the allylic moieties to yield blanched homoallylic alcohols with anti diasteroselectivity. On the other hand, trapping with silyl chlorides produced linear allylic silanes. Here, a plausible mechanism to account for the difference is proposed.
• Bateson, John H.; Quinn, Alison M.; Smale, Terence C., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2219 - 2234
  作者：Bateson, John H.、Quinn, Alison M.、Smale, Terence C.、Southgate, Robert

  DOI：——

  日期：——
• Silylene oxonium ylides: di-tert-butylsilylene insertion into C–O bonds
  作者：Laura E. Bourque、Pamela A. Haile、Janice M.N. Loy、K.A. Woerpel

  DOI：10.1016/j.tet.2009.04.016

  日期：2009.7

  Allylic ethers undergo insertions of silylenes into C-O bonds to form allylic silanes. Silylene insertion into C-O acetal bonds was also observed. Formation of silylene ylide intermediates led to [ 1,2]-Stevens rearrangement products as well as [2,3]-sigmatropic products depending upon the steric environment of the starting allylic ether. (C) 2009 Elsevier Ltd. All rights reserved.
• Metal-Catalyzed Silylene Insertions of Allylic Ethers:  Stereoselective Formation of Chiral Allylic Silanes
  作者：Laura E. Bourque、Pamela A. Cleary、K. A. Woerpel

  DOI：10.1021/ja073758s

  日期：2007.10.1

  Silylene insertion into allylic ethers occurs suprafacially to provide enantioenriched allylic silanes and disilanes. Silylene insertion to a variety of protected allylic alcohols utilizing silver- and copper-mediated conditions proved to be a general method for allylic silane formation. Allylic disilanes reacted similarly to allylic silanes, undergoing both annulation and allylation reactions.

  亚甲硅烷插入烯丙基醚发生在表面上以提供对映体富集的烯丙基硅烷和乙硅烷。利用银和铜介导的条件将亚甲硅烷插入各种受保护的烯丙醇被证明是形成烯丙硅烷的通用方法。烯丙基乙硅烷的反应与烯丙基硅烷类似，同时发生环化和烯丙基化反应。