(E/Z)-1-<(tert-butyldimethylsilyl)oxy>-2-methoxy-4-(1-propenyl)benzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E/Z)-1-<(tert-butyldimethylsilyl)oxy>-2-methoxy-4-(1-propenyl)benzene
• 英文别名: tert-butyl(2-methoxy-4-(prop-1-en-1-yl)phenoxy)dimethylsilane；1-(3'-t-butyldimethylsiloxy-4'-methoxyphenyl)propene
• 化学式: C₁₆H₂₆O₂Si
• 分子量: 278.467
• InChiKey: JBLRFLBAAUUBPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E/Z)-1-<(tert-butyldimethylsilyl)oxy>-2-methoxy-4-(1-propenyl)benzene 在 四丁基氟化铵 、 四氯化钛 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 0.42h， 生成 (+/-)-(2α,4α,5β,5aα)-4-(4-hydroxy-3-methoxyphenyl)-2,5a-methano-7-methoxy-5-methyl-8H-2,3,4,5-tetrahydro-1-benzoxepin-8-one
  参考文献：
  名称：

  Synthesis of neolignans via a proposed biosynthetic intermediate. Total synthesis of (.+-.)-futoenone

  摘要：

  The attempted spectroscopic observation of a quinone methide proposed to be an intermediate in the biosynthesis of neolignans is reported. The results afforded substantial indirect evidence for the formation of quinone methide 3. The synthesis of racemic bicyclo[3.2.1]octenedione 22, a natural product, is proposed to occur through a similar quinone methide intermediate. The synthesis of (+/-)-futoenone via a benzylic cation intermediate related to quinone methide 3 is reported. The results provide support for Gottlieb's proposal that several different neolignans arise from a common biosynthetic precursor. The efficient synthesis of (+/-)-futoenone and related spiro[5.5]undecanoids using a Buchi quinone ketal cycloaddition is also described.

  DOI：

  10.1021/jo00072a017
• 作为产物：
  描述：

  tert-butyl(2-methoxy-4-propylphenoxy)dimethylsilane 在 3,3-二甲基-1-丁烯 、 C₂₀H₃₅IrO₂P₂ 作用下， 以 甲苯 为溶剂， 生成 (E/Z)-1-<(tert-butyldimethylsilyl)oxy>-2-methoxy-4-(1-propenyl)benzene
  参考文献：
  名称：

  通过烷基链脱氢进行位点和对映选择性均苯甲基 C(sp3)–H 硼基化

  摘要：

  开发了一种基于脱氢的一锅式 Ir/Co/Cu 三重催化，用于同苄基 C(sp 3 )–H 键的正式不对称硼基化，直接从简单的芳基烷烃提供具有 β-立体中心的对映体富集的有机硼酸酯。机理研究表明，Ir 催化剂负责将芳基烷烃脱氢为 1-芳基烯烃，然后进行 Cu 催化的 ( E )-芳基烯烃的区域选择性和对映选择性原硼化反应；发现将 ( Z )-烯烃共催化立体异构化为 ( E )-异构体对生产率和对映选择性具有有益影响。

  DOI：

  10.1021/acs.orglett.4c02746

文献信息

• Enantioselective Olefin Hydrocyanation without Cyanide
  作者：Alexander W. Schuppe、Gustavo M. Borrajo-Calleja、Stephen L. Buchwald

  DOI：10.1021/jacs.9b10875

  日期：2019.11.27

  The enantioselective hydrocyanation of olefins represents a conceptually straightforward approach to prepare enantiomerically enriched nitriles. These, in turn, comprise or are intermediates in the synthesis of many pharmaceuticals and their synthetic derivatives. Herein, we report a cyanide-free dual Pd/CuH-catalyzed protocol for the asymmetric Markovnikov hydrocyanation of vinyl arenes and the anti-Markovnikov

  烯烃的对映选择性氢氰化代表了一种概念上简单的制备对映体富集腈的方法。这些反过来又包含或是许多药物及其合成衍生物的合成中间体。在此，我们报告了一种无氰化物双 Pd/CuH 催化方案，用于乙烯基芳烃的不对称 Markovnikov 氢氰化和末端烯烃的反 Markovnikov 氢氰化，其中恶唑用作腈等价物。在最初的加氢芳基化过程之后，使用 [4+2]/retro-[4+2] 序列解构恶唑亚结构，在温和的反应条件下提供对映体富集的腈产物。
• Synthesis and evaluation of double bond substituted combretastatins
  作者：John A. Hadfield、Keira Gaukroger、Nicholas Hirst、Anna P. Weston、Nicholas J. Lawrence、Alan T. McGown

  DOI：10.1016/j.ejmech.2004.12.008

  日期：2005.6

  A series of cornbretastatins substituted with epoxides, amides and small alkyl groups has been synthesised and evaluated for cytotoxicity and their ability to inhibit the assembly of tubulin. The methyl and ethyl substituted phenols 36, 44 have shown potent antimitotic effects whilst exhibiting reduced cytotoxicity. (c) 2005 Elsevier SAS. All rights reserved.
• Synthesis of neolignans via a proposed biosynthetic intermediate. Total synthesis of (.+-.)-futoenone
  作者：Steven R. Angle、Kenneth D. Turnbull

  DOI：10.1021/jo00072a017

  日期：1993.9

  The attempted spectroscopic observation of a quinone methide proposed to be an intermediate in the biosynthesis of neolignans is reported. The results afforded substantial indirect evidence for the formation of quinone methide 3. The synthesis of racemic bicyclo[3.2.1]octenedione 22, a natural product, is proposed to occur through a similar quinone methide intermediate. The synthesis of (+/-)-futoenone via a benzylic cation intermediate related to quinone methide 3 is reported. The results provide support for Gottlieb's proposal that several different neolignans arise from a common biosynthetic precursor. The efficient synthesis of (+/-)-futoenone and related spiro[5.5]undecanoids using a Buchi quinone ketal cycloaddition is also described.