(E)-3-phenylprop-2-en-1-yl 3-oxopentanoate | 741262-35-1

• 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: (E)-3-phenylprop-2-en-1-yl 3-oxopentanoate
• 英文别名: (3-phenyl-2-propene-1-yl) 3-oxovalerate；[(E)-3-phenylprop-2-enyl] 3-oxopentanoate
• CAS: 741262-35-1
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: CXEDBYHNIXLNIC-RMKNXTFCSA-N

物化性质

• 沸点：
  371.3±30.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-phenylprop-2-en-1-yl 3-oxopentanoate 在 1,1'-bipyridyl 作用下， 以 二氯甲烷 为溶剂， 生成 5-phenyl-6-hepten-3-one
  参考文献：
  名称：

  Ruthenium-Catalyzed Decarboxylative Allylation of Nonstabilized Ketone Enolates

  摘要：

  Bipyridyl(pentamethylcyclopentadienyl)ruthenium chloride is an efficient catalyst for the formal [3,3] rearrangement of allyl beta-ketoesters. The mechanism of the transformation involves formation of pi-allyl ruthenium intermediates, which are selectively attacked at the more substituted allyl terminus by freely diffusing enolates. Decarboxylation of beta-ketocarboxylates allows generation of enolates under extremely mild conditions.

  DOI：

  10.1021/ol049097a
• 作为产物：
  描述：

  3-氧代戊酸甲酯 、 3-苯基丙-2-烯-1-醇 在 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 以84%的产率得到(E)-3-phenylprop-2-en-1-yl 3-oxopentanoate
  参考文献：
  名称：

  Dihydropyridine derivative

  摘要：

  二氢吡啶衍生物具有以下结构式，其类似物和药学上可接受的盐具有选择性抑制N型钙通道作用的活性。它们被用作治疗与N型钙通道相关的各种疾病，如脑梗死发作后急性期内由缺血引起的脑病、脑出血或类似疾病、阿尔茨海默病等。

  公开号：

  US06350766B1

文献信息

• CpRuII-chiral bisamidine complex catalyzed asymmetric Carroll-type decarboxylative allylation of β-keto allyl esters
  作者：Shintarou Ogawa、Kengo Miyata、Sho Kawakami、Shinji Tanaka、Masato Kitamura

  DOI：10.1016/j.tet.2019.130888

  日期：2020.2

  that of the previously reported examples. The developed reaction system displays improved regioselectivity and enantioselectivity and a broad substrate scope. Mechanistic studies using NMR experiments, substrate-structure/reactivity relationship studies, and cross-over experiment reveal a possible reaction pathway involving the enolate of the β-keto acid.

  报道了β-酮烯丙基酯与带有手性双am型二齿配体的阳离子CpRu配合物的卡洛尔重排型分子内脱羧烯丙基化。该催化体系允许将β-酮酸的单取代的3-芳基烯丙基酯有效地转化为相应的γ，δ-烯酮。明显地，催化转化率比先前报道的实例的催化转化率高一个数量级。发达的反应系统显示出改进的区域选择性和对映选择性以及广泛的底物范围。使用NMR实验的机理研究，底物结构/反应性关系研究和交叉实验揭示了可能的反应途径，其中涉及β-酮酸的烯醇化物。
• Ruthenium-Catalyzed Decarboxylative Insertion of Electrophiles
  作者：Chao Wang、Jon A. Tunge

  DOI：10.1021/ol050466s

  日期：2005.5.1

  A ruthenium complex, Cp*Ru(bipyridyl)CI, has been developed as a catalyst for the first regioselective tandem Michael addition-allylic alkylation of activated Michael acceptors. The net transformation is the decarboxylative insertion of Michael acceptors into allyl beta-ketoesters.
• Dihydropyridine derivative
  申请人：Ajinomoto Co., Inc.

  公开号：US06350766B1

  公开（公告）日：2002-02-26

  Dihydropyridine derivatives of the following formula, analogs thereof and pharmaceutically acceptable salts thereof have an activity of selectively inhibiting the action of N-type calcium channel. They are used as remedies for various diseases relating to the N-type calcium channel such as encephalopathies caused by the ischemia in the acute phase after the onset of cerebral infarction, cerebral hemorrhage or the like, Alzheimer's disease, etc.

  二氢吡啶衍生物具有以下结构式，其类似物和药学上可接受的盐具有选择性抑制N型钙通道作用的活性。它们被用作治疗与N型钙通道相关的各种疾病，如脑梗死发作后急性期内由缺血引起的脑病、脑出血或类似疾病、阿尔茨海默病等。
• Ruthenium-Catalyzed Decarboxylative Allylation of Nonstabilized Ketone Enolates
  作者：Erin C. Burger、Jon A. Tunge

  DOI：10.1021/ol049097a

  日期：2004.7.1

  Bipyridyl(pentamethylcyclopentadienyl)ruthenium chloride is an efficient catalyst for the formal [3,3] rearrangement of allyl beta-ketoesters. The mechanism of the transformation involves formation of pi-allyl ruthenium intermediates, which are selectively attacked at the more substituted allyl terminus by freely diffusing enolates. Decarboxylation of beta-ketocarboxylates allows generation of enolates under extremely mild conditions.