2,2-dimethyl-5-phenyl-4-pentenal | 198283-76-0

• 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: 2,2-dimethyl-5-phenyl-4-pentenal
• 英文别名: 2,2-dimethyl-5-phenylpent-4-enal
• CAS: 198283-76-0
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: ZQNBCNJBAWIUKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-phenyl-4-pentenal 在 rhodium(II) acetate dimer 、 氧气 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 3,4-epoxy-2-methyl-4-phenyl-butan-2-ol 、
  参考文献：
  名称：

  Rhodium acetate-catalyzed aerobic Mukaiyama epoxidation of alkenes

  摘要：

  Mukaiyama epoxidation of alkenes under oxygen catalyzed by rhodium acetate with isobutyraldehyde as the reducing agent is as or more effective than previously reported procedures. A variety of alkenes, including terpenes and cholesterol derivatives, were oxidized. And high regioselectivity for mono-epoxidation was observed with neryl, geranyl, and linalyl acetates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.062
• 作为产物：
  描述：

  肉桂醇 、 异丁醛 在 bis(η3-allyl-μ-chloropalladium(II)) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 DL-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 以78%的产率得到2,2-dimethyl-5-phenyl-4-pentenal
  参考文献：
  名称：

  烯丙基醇对可烯化酮和醛的钯和脯氨酸双重烷基烯丙基烷基化反应

  摘要：

  描述了多种可烯化的酮和醛与烯丙基醇的双重Pd /脯氨酸催化的α-烯丙基化反应。在该反应中，选择大咬角配体Xantphos和脯氨酸作为有机催化剂对于从烯丙醇生成关键的π-烯丙基Pd中间体至关重要，然后由相应的可烯醇化羰基原位形成烯胺进行亲核攻击底物和脯氨酸。

  DOI：

  10.1021/ol9001812

文献信息

• Rhodium acetate-catalyzed aerobic Mukaiyama epoxidation of alkenes
  作者：Dmitry Shabashov、Michael P. Doyle

  DOI：10.1016/j.tet.2013.09.062

  日期：2013.11

  Mukaiyama epoxidation of alkenes under oxygen catalyzed by rhodium acetate with isobutyraldehyde as the reducing agent is as or more effective than previously reported procedures. A variety of alkenes, including terpenes and cholesterol derivatives, were oxidized. And high regioselectivity for mono-epoxidation was observed with neryl, geranyl, and linalyl acetates. (C) 2013 Elsevier Ltd. All rights reserved.
• Dual Palladium- and Proline-Catalyzed Allylic Alkylation of Enolizable Ketones and Aldehydes with Allylic Alcohols
  作者：Ippei Usui、Stefan Schmidt、Bernhard Breit

  DOI：10.1021/ol9001812

  日期：2009.3.19

  The dual Pd/proline-catalyzed α-allylation reaction of a variety of enolizable ketones and aldehydes with allylic alcohols is described. In this reaction, the choice of a large-bite angle ligand Xantphos and proline as the organocatalyst was essential for generation of the crucial π-allyl Pd intermediate from allylic alcohol, followed by nucleophilic attack of the enamine formed in situ from the corresponding

  描述了多种可烯化的酮和醛与烯丙基醇的双重Pd /脯氨酸催化的α-烯丙基化反应。在该反应中，选择大咬角配体Xantphos和脯氨酸作为有机催化剂对于从烯丙醇生成关键的π-烯丙基Pd中间体至关重要，然后由相应的可烯醇化羰基原位形成烯胺进行亲核攻击底物和脯氨酸。