3-(6-tert-butyldimethylsilyloxy-1-hexen)-yl benzoate | 1266356-15-3

• 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: 3-(6-tert-butyldimethylsilyloxy-1-hexen)-yl benzoate
• 英文别名: 6-[Tert-butyl(dimethyl)silyl]oxyhex-1-en-3-yl benzoate
• CAS: 1266356-15-3
• 化学式: C₁₉H₃₀O₃Si
• 分子量: 334.531
• InChiKey: ATXBUCKUGHUQNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲酸 、 [(Z)-6-[tert-butyl(dimethyl)silyl]oxyhex-2-enyl] 2,2,2-trichloroethanimidate 在 (-)-(S)-COP-OAc 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以93%的产率得到3-(6-tert-butyldimethylsilyloxy-1-hexen)-yl benzoate
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Chiral Allylic Esters

  摘要：

  Trichloroacetimidate derivatives of prochiral (Z)-2-alken-1-ols react at room temperature with carboxylic acids to give chiral 3-acyloxy-1-alkenes in high enantiopurity in the presence of di-mu-acetatobis[(eta5-(S)-(pR)-2-(2'-(4'-methylethyl)oxazolinyl)cyclopentadienyl,1-C,3'-N)(eta4-tetraphenylcyclobutadiene)cobalt]dipalladium (COP-OAc) or its enantiomer. This reaction has broad scope, proceeds with predictable high stereoinduction, is accomplished at room temperature using high substrate concentrations and low catalyst loadings, and likely proceeds by a novel mechanism.

  DOI：

  10.1021/ja0425583

文献信息

• Copper-catalyzed regioselective allylic oxidation of olefins via C–H activation
  作者：Nengbo Zhu、Bo Qian、Haigen Xiong、Hongli Bao

  DOI：10.1016/j.tetlet.2017.09.047

  日期：2017.10

  A regioselective oxidation of allylic C–H bond to C–O bond catalyzed by copper (I) was developed with diacyl peroxides as oxidants. The oxidation of allylic C–H bond was accomplished with good yield and regioselectivity under mild reaction conditions. This method has a broad substrate scope including cyclic olefins, terminal and internal acyclic olefins and allyl benzene compounds. The reaction proceeds

  以二酰基过氧化物为氧化剂，开发了由铜（I）催化的烯丙基CH键至CH键的区域选择性氧化。在温和的反应条件下，烯丙基CH键的氧化反应具有良好的收率和区域选择性。该方法具有广泛的底物范围，包括环烯烃，末端和内部无环烯烃以及烯丙基苯化合物。如自旋俘获实验所建议的，反应是通过自由基机理进行的。
• Redox-Neutral Atom-Economic Rhodium-Catalyzed Coupling of Terminal Alkynes with Carboxylic Acids Toward Branched Allylic Esters
  作者：Alexandre Lumbroso、Philipp Koschker、Nicolas R. Vautravers、Bernhard Breit

  DOI：10.1021/ja1108613

  日期：2011.3.2

  A new method for the preparation of a wide range of branched allylic esters from terminal alkynes that proceeds via a redox-neutral propargylic CH activation employing a rhodium(I)/DPEphos catalyst is reported.