(E)-tert-butyl 3,5-dioxo-7-phenylhept-6-enoate | 121712-56-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-tert-butyl 3,5-dioxo-7-phenylhept-6-enoate
• 英文别名: tert-butyl (E)-3,5-dioxo-7-phenylhept-6-enoate
• CAS: 121712-56-9
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: AQDDBMVTIJJGLE-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  肉桂酸 在 正丁基锂 、 草酰氯 、 sodium hydride 、 三乙胺 作用下， 反应 1.83h， 生成 (E)-tert-butyl 3,5-dioxo-7-phenylhept-6-enoate
  参考文献：
  名称：

  N-acyl aziridines - C-acylating agents for the preparation of polyketides

  摘要：

  A one-pot synthesis of N-acylaziridines from carboxylic acids has been developed, and their reaction with dianions derived from beta-ketoesters studied. The aziridines were found to be efficient C-acylating agents, giving polyketide-like products in good overall yields.

  DOI：

  10.1016/s0040-4039(00)73323-5

文献信息

• N-Acyl-2-methylaziridines: Synthesis and utility in the C-acylation of β-ketoester derived dianions
  作者：Barry Lygo

  DOI：10.1016/0040-4020(95)00820-x

  日期：1995.11

  A “one pot” method for the preparation of N-acyl-2-methylaziridines is described, and the utility of these compounds in the C-acylation of dianions derived from β-ketoesters investigated. Application of this methodology to the synthesis of the polyketide natural product yangonin is also described.

  描述了用于制备N-酰基-2-甲基氮丙啶的“一锅法”，并且研究了这些化合物在衍生自β-酮酸酯的二价阴离子的C-酰化中的用途。还描述了该方法在聚酮化合物天然产物仰光宁合成中的应用。
• Stereoselective Reduction of<i>β</i>,<i>δ</i>-Diketo Esters. A Novel Strategy for the Synthesis of Artificial HMG-CoA Reductase Inhibitors
  作者：Tamejiro Hiyama、Guntoori Bhaskar Reddy、Tatsuya Minami、Takeshi Hanamoto

  DOI：10.1246/bcsj.68.350

  日期：1995.1

  Condensation of N-methoxy-N-methyl amides with the dianions of acetoacetates gives in good yields β,δ-diketo esters, which are reduced with Et2BOMe–NaBH4 in tetrahydrofuran–methanol highly selectively to give syn-β,δ-dihydroxy esters in one step. Similarly, the β,δ-diketo esters of the Taber’s chiral alcohol or its enantiomer respectively are reduced to give syn-β,δ-dihydroxy esters of moderate enantiomeric excess. Higher diastereo- and enantioselectivity were achieved by reduction of the β,δ-diketo esters of the Taber’s chiral alcohol or its enantiomer successively with diisobutylalane and with Et2BOMe–NaBH4. The resulting syn-diol esters were hydrolyzed and lactonized to give various types of β-hydroxy-δ-lactones commonly found in artificial HMG-CoA reductase inhibitors.

  N-甲氧基-N-甲基酰胺与乙酰乙酸酯的二阴离子缩合，高产率地得到了β，δ-二酮酯，这些二酮酯在四氢呋喃-甲醇中与Et2BOMe-NaBH4还原，高度选择性地一步得到syn-β，δ-二羟基酯。类似地，Taber的手性醇或其对映体的β，δ-二酮酯分别还原得到中等对映体纯度的syn-β,δ-二羟基酯。通过先后使用二异丁基铝烷和Et2BOMe-NaBH4还原Taber的手性醇或其对映体的β,δ-二酮酯，获得了更高的非对映选择性和对映选择性。得到的syn-二醇酯经水解和内酯化得到多种常见于人工HMG-CoA还原酶抑制剂中的β-羟基-δ-内酯。
• A facile entry to β,δ-diketo and syn-β,δ-dihydroxy esters
  作者：Takeshi Hanamoto、Tamejiro Hiyama

  DOI：10.1016/s0040-4039(00)82375-8

  日期：1988.1
• Barry Lygo, Tetrahedron Lett, 35 (1994) N 28, S 5073-5074
  作者：Barry Lygo

  DOI：——

  日期：——
• HANAMOTO, TAKESHI;HIYAMA, TAMEJIRO, TETRAHEDRON LETT., 29,(1988) N 49, C. 6467-6470
  作者：HANAMOTO, TAKESHI、HIYAMA, TAMEJIRO

  DOI：——

  日期：——