1-苯基-3-丁烯基苯甲酸酯 | 133621-29-1

• 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: 1-苯基-3-丁烯基苯甲酸酯
• 英文名称: 1-phenyl-3-butenyl benzoate
• 英文别名: 1-Phenylbut-3-enyl benzoate
• CAS: 133621-29-1
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: UMASIPMQYMZJCM-UHFFFAOYSA-N

物化性质

• 沸点：
  364.7±21.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苯基-3-丁烯基苯甲酸酯 在 四氯化钛 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 3-Methoxy-1-phenyl-5-phenylsulfanylmethyl-hex-5-en-1-ol
  参考文献：
  名称：

  [3 + 3]通过连续两个电子和一个电子烯丙基化的环

  摘要：

  3-苯硫基-2-（三甲基甲硅烷基甲基）丙烯是通过[3 + 3]环合法制备亚甲基环己烷的方便的辅助试剂。三甲基甲硅烷基可促进路易斯酸催化的醛或乙缩醛的烯丙基化，而苯硫基可指导6-内-trig自由基环化反应。

  DOI：

  10.1016/s0040-4039(00)92100-2
• 作为产物：
  描述：

  苯甲醛 在 吡啶 作用下， 以 乙醚 为溶剂， 生成 1-苯基-3-丁烯基苯甲酸酯
  参考文献：
  名称：

  [3 + 3]通过连续两个电子和一个电子烯丙基化的环

  摘要：

  3-苯硫基-2-（三甲基甲硅烷基甲基）丙烯是通过[3 + 3]环合法制备亚甲基环己烷的方便的辅助试剂。三甲基甲硅烷基可促进路易斯酸催化的醛或乙缩醛的烯丙基化，而苯硫基可指导6-内-trig自由基环化反应。

  DOI：

  10.1016/s0040-4039(00)92100-2

文献信息

• In Situ Formation of Allyl Ketones via Hiyama−Nozaki Reactions Followed by a Chromium-Mediated Oppenauer Oxidation
  作者：Henri S. Schrekker、Martin W. G. de Bolster、Romano V. A. Orru、Ludger A. Wessjohann

  DOI：10.1021/jo001750u

  日期：2002.4.1

  dependent on the substitution pattern of the reaction partners and the reaction conditions. An appropriate choice of these can lead to preferential formation of ketones instead of the alcohols. In addition to its synthetic usefulness, the oxidation-reduction equilibrium is of the utmost importance for the design of enantioselective Hiyama-Nozaki reactions because it is also a potential racemization pathway

  在烯丙基铬与醛的Hiyama-Nozaki反应中，预期产物为均烯丙基醇。然而，衍生自这些的氧化产物，主要是烯丙基酮，可以是常见的副产物。这可以通过Oppenauer-（Meerwein-Ponndorf-Verley）类型的机制（OMPV反应）来解释。氧化量在很大程度上取决于反应伙伴的取代方式和反应条件。的这些适当的选择可导致优先形成酮代替醇。除了其合成用途外，氧化还原平衡对于对映选择性Hiyama-Nozaki反应的设计也至关重要，因为它也是潜在的消旋途径。
• Allylation of Aldehydes by Allyl- and Crotyltributyltin in the Presence of Catalytic Amounts of Bu₂SnCl₂Complex
  作者：Katsunori Yano、Akio Baba、Haruo Matsuda

  DOI：10.1246/bcsj.65.66

  日期：1992.1

  In nearly neutral media, the reaction of allylic tributyltin with aldehydes is effectively catalyzed by Bu2SnCl2 complexes. The addition of coordinative reagents and benzoyl chloride as a quencher is required of the catalytic allylation, furnishing homoallyl benzoates in good to excellent yields, where a regioreversed coupling to conventional methods using crotyltributyltin is exclusively observed.

  在接近中性的介质中，烯丙基三丁基锡与醛的反应可由 Bu2SnCl2 复合物有效催化。催化烯丙基化反应时需要加入配位试剂和苯甲酰氯作为淬灭剂，以良好到极佳的产率获得均烯丙基苯甲酸酯，与使用巴豆三丁基锡的传统方法相比，这种反应只出现了逆向偶联。
• A convenient synthesis of protected and free homoallylic alcohols: Catalytic use of dibutyltin dichloride in the allylation of aldehydes with allyltributyltin
  作者：James K. Whitesell、Richard Apodaca

  DOI：10.1016/0040-4039(96)00719-8

  日期：1996.6

  A new procedure for the allylation of aldehydes with allyltributyltin in the presence of 10 mol% dibutyltin dichloride and either an acid chloride or trimethylsilyl chloride has been developed. Homoallylic esters, carbonates, trimethylsilyl ethers, and alcohols were obtained in up to 99% yield.

  已经开发了在10mol％二丁基二氯化锡和酰氯或三甲基甲硅烷基氯存在下醛与烯丙基三丁基锡烯丙基化的新方法。以高达99％的产率获得了均烯丙基酯，碳酸酯，三甲基甲硅烷基醚和醇。
• Greening the Wacker process
  作者：Mukund G. Kulkarni、Yunnus B. Shaikh、Ajit S. Borhade、Sanjay W. Chavhan、Attrimuni P. Dhondge、Dnyaneshwar D. Gaikwad、Mayur P. Desai、Deekshaputra R. Birhade、Nagorao R. Dhatrak

  DOI：10.1016/j.tetlet.2013.01.082

  日期：2013.5

  Wacker oxidation of various terminal olefins with Pd-0/C-KBrO3, a nontoxic, environmentally benign, and easy to handle catalyst system, was achieved in high isolated yields. The described protocol offers an alternative to the traditional Wacker system which uses CuCl2 as co-catalyst. The catalyst is reusable while maintaining high activity and selectivity. (C) 2013 Elsevier Ltd. All rights reserved.
• [3 + 3] Annulation Based on 6-Endo-Trig Radical Cyclization: Regioselectivity and Diastereoselectivity
  作者：Dale E. Ward、Yuanzhu Gai、Brian F. Kaller

  DOI：10.1021/jo00129a024

  日期：1995.12

  The development of a [3 + 3] annulation strategy based on sequential ''two-electron'' and ''one-electron'' allylation of beta-substituted aldehydes and derivatives with the bifunctional isobutene conjunctive reagent 1 is described. The key step involves an unusual 6-endo-trig radical cyclization. Yields of 6-endo products are improved if the PhS group is oxidized to a PhSO(2) group prior to cyclization. The structural factors affecting the regioselectivity and stereoselectivity of the cyclization are examined. In general, the stereoselectivity of 6-endo-trig cyclization of 5-hexenyl radicals can be rationalized by conformational analysis of chairlike transition states and can be calculated effectively with an MM2 force field model, High 6-endo regioselectivity requires a strong driving force. Fragmentable allylic groups (R(3)Sn, PhSO(2), and to a lesser extent PhS) are shown to be sufficiently activating to achieve 6-endo regioselectivity.