Tert-butyl 5-phenylpent-2-enoate | 136886-54-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Tert-butyl 5-phenylpent-2-enoate
• CAS: 136886-54-9
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: GWCSUDMQETXHDC-UHFFFAOYSA-N

物化性质

• 沸点：
  325.0±21.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  Tert-butyl 5-phenylpent-2-enoate 在 草酰氯 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 溶剂黄146 、 三乙胺 、 lithium benzyl-(R)-1-phenylethylamide 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 91.0h， 生成 C₁₈H₁₈ClNO₂
  参考文献：
  名称：

  Enantiopure 3-Amino-Substituted 1-Indanones, 1-Tetralones, and 1-Benzosuberones via Friedel–Crafts Cyclisation of ω-Aryl-β-benz­amido Acids

  摘要：

  Conjugate addition of enantiopure lithium (R)-N-benzyl-N-(-methylbenzyl)amide to a range of -aryl-,-unsaturated esters gives the corresponding -aryl--amino esters as single diastereoisomers in high yields. Friedel-Crafts cyclisation of the pendant carbonyl group onto the -aryl ring then gives a range of 3-amino-substituted 1-indanones, 1-tetralones, and 1-benzosuberones, representing an efficient and short protocol for the preparation of these benzo-fused carbocycles in enantiopure form.

  DOI：

  10.1055/s-0034-1380675

文献信息

• Enantioselective bifunctional iminophosphorane catalyzed sulfa-Michael addition of alkyl thiols to unactivated β-substituted-α,β-unsaturated esters
  作者：Jinchao Yang、Alistair J. M. Farley、Darren J. Dixon

  DOI：10.1039/c6sc02878k

  日期：——

  The highly enantioselective sulfa-Michael addition of alkyl thiols to unactivated β-substituted-α,β-unsaturated esters catalyzed by a bifunctional iminophosphorane (BIMP) organocatalyst is described.

  烷基硫醇对未活化的β-取代-α,β-不饱和酯的高对映选择性磺酰-迈克尔加成反应，由双功能亚磷酰胺（BIMP）有机催化剂催化。
• Synthesis and Applications of Unquaternized C-Bound Boron Enolates
  作者：Elvis Wang Hei Ng、Kam-Hung Low、Pauline Chiu

  DOI：10.1021/jacs.8b00614

  日期：2018.3.14

  boron enolates by a ligand-controlled O-to-C isomerization is reported. Using this protocol, C-bound pinacolboron enolates have been isolated in pure form for the first time, and have been fully characterized by NMR spectroscopy and X-ray crystallography. In contrast to the general perception, such C-boron enolates are stable without coordinative saturation at the boron. Moreover, C-boron enolates present

  报道了一种通过配体控制的 O-to-C 异构化制备未季铵化 C 结合硼烯醇化物的通用和简便方法。使用该协议，首次以纯形式分离了 C 结合的频哪醇烯醇化物，并通过核磁共振光谱和 X 射线晶体学进行了充分表征。与一般看法相反，这种 C-硼烯醇化物是稳定的，在硼处没有配位饱和。此外，C-硼烯醇化物呈现出与O-硼烯醇化物不同的反应性，并且证明了它们在CO和CC键形成中的应用。
• <i>anti</i>-Selective synthesis of β-boryl-α-amino acid derivatives by Cu-catalysed borylamination of α,β-unsaturated esters
  作者：Soshi Nishino、Yuji Nishii、Koji Hirano

  DOI：10.1039/d2sc06003e

  日期：——

  borylamination of α,β-unsaturated esters with B2pin2 and hydroxylamines has been developed to deliver acyclic β-boryl-α-amino acid derivatives with high anti-diastereoselectivity (up to >99 : 1), which is difficult to obtain by the established methods. A chiral phosphoramidite ligand also successfully induces the enantioselectivity, giving the optically active β-borylated α-amino acids. The products can be stereospecifically

  已开发出铜催化的 α,β-不饱和酯与 B 2 pin 2和羟胺的区域选择性和非对映选择性硼胺化，以提供具有高抗非对映选择性（高达 >99 : 1）的无环 β-硼基-α-氨基酸衍生物），用现有的方法很难得到。手性亚磷酰胺配体也成功地诱导了对映选择性，产生光学活性的β-硼化α-氨基酸。该产品可以立体定向地转化为β-功能化的α-氨基酸，这在药物化学领域具有重要意义。
• Indium/copper-mediated conjugate addition of unactivated alkyl iodides to α,β-unsaturated carbonyl compounds in water
  作者：Zhi-Liang Shen、Hao-Lun Cheong、Teck-Peng Loh

  DOI：10.1016/j.tetlet.2008.12.079

  日期：2009.3

  An efficient method for the conjugate addition of unactivated alkyl iodides to alpha,beta-Unsaturated carbonyl compounds using indium/copper in water is described. The reactions proceed more efficiently in water than in organic solvents. In, CuI, and InCl3 are all essential for efficient reaction. Formation of a symmetrical vic-diarylalkane is observed when an aryl-substituted alkene is used as substrate. (C) 2009 Elsevier Ltd. All rights reserved.
• Stereocontrolled Fluorobenzylation of Vinyl Sulfones and α,β-Unsaturated Esters Mediated by a Remote Sulfinyl Group. Synthesis of Functionalized Enantiomerically Pure Benzylic Fluorides
  作者：José Luis García Ruano、José Antonio Fernández-Salas、M. Carmen Maestro

  DOI：10.1021/jo300174k

  日期：2012.3.16

  A sulfinyl group in an ortho position confers enough chemical and configurational stability to monofluorobenzylcarbanions to evolve in a completely stereoselective way in their reactions with beta-substituted vinyl sulfones and alpha,beta-unsaturated esters. Reactions afford easily separable mixtures of two epimers differing in the configuration of the center derived from the Michael acceptor (up to 98% de). They can be easily converted into enantiomerically pure gamma-fluorinated gamma-phenylsulfones and gamma-phenylesters bearing two chiral centers.