ethyl 4-bromo-2,2-dimethyl-3-oxopentanoate | 646534-01-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 4-bromo-2,2-dimethyl-3-oxopentanoate
• CAS: 646534-01-2
• 化学式: C₉H₁₅BrO₃
• 分子量: 251.12
• InChiKey: FGRPHSNILDFPTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  94-95 °C(Press: 22 Torr)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  ethyl 4-bromo-2,2-dimethyl-3-oxopentanoate 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 57.0h， 生成 (E)-ethyl 3-oxo-5-phenyl-2,2,4-trimethylpent-4-enoate
  参考文献：
  名称：

  A multicomponent coupling strategy suitable for the synthesis of the triene component of the oxazolomycin antibioticsThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.

  摘要：

  报道了适用于合成oxazolomycin左旋三烯子单元类似物的三种几何异构体的简明且多功能的路线。基于关键Heck反应的策略未能成功，这归因于烯烃底物的空间阻碍和电子失活。然而，另一种Stille偶联策略既多功能又高产，且有可能适用于合成侧链几何结构和末端芳香或杂芳香残基不同的类似物。

  DOI：

  10.1039/b306925g
• 作为产物：
  描述：

  2-甲基-3-氧代戊酸乙酯 在 溴 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 26.17h， 生成 ethyl 4-bromo-2,2-dimethyl-3-oxopentanoate
  参考文献：
  名称：

  A multicomponent coupling strategy suitable for the synthesis of the triene component of the oxazolomycin antibioticsThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.

  摘要：

  报道了适用于合成oxazolomycin左旋三烯子单元类似物的三种几何异构体的简明且多功能的路线。基于关键Heck反应的策略未能成功，这归因于烯烃底物的空间阻碍和电子失活。然而，另一种Stille偶联策略既多功能又高产，且有可能适用于合成侧链几何结构和末端芳香或杂芳香残基不同的类似物。

  DOI：

  10.1039/b306925g

文献信息

• A Multicomponent Coupling Strategy for the Synthesis of the Triene Component of the Oxazolomycin Antibiotics
  作者：Mark G. Moloney、Paul G. Bulger、Paul C. Trippier

  DOI：10.1055/s-2002-34905

  日期：——

  Concise and versatile routes suitable for the synthesis of three geometric isomers of an analogue of the left hand triene sub-unit of oxazolomycin are reported, using a Stille coupling strategy.

  报道了利用Stille偶联策略，合成左旋噁唑霉素左手三烯亚基类似物的三种几何异构体的简捷且通用的路线。
• ——
  作者：V. V. Shchepin、Yu. Kh. Sazhneva、D. N. Litvinov

  DOI：10.1023/a:1025600905960

  日期：——

  Zinc enolates formed from ethyl 4-bromo-2,2,4-trimethyl-3-oxopentanoate react under the conditions of one- of two-stage synthesis with aliphatic, unsaturated, or aromatic aldehydes to form 6-R-2,2,4,4-tetramethyl-2,3,5,6-tetrahydropyran-2,4-diones. Zinc enolates obtained from ethyl 4-bromo-2,2-dimethyl-3-oxopentanoate, -hexanoate, and -2,2,5-trimethyl-3-oxohexanoate under the similar conditions react with aliphatic or aromatic aldehydes to give mainly 5-R-1-6-R-2-3,3-dimethyl-2,3,5,6-tetrahydropyran-2,4-diones as E or Z isomers or their mixtures. Zinc enolates generated from the ethyl 4-bromo-2,2-diethyl- or 2-benzyl-2-ethyl-3-oxobutanoates react with aromatic aldehydes to give ethyl 5-R-2-R-2-ethyl-3-oxo-4-pentenoates as E isomers.
• A multicomponent coupling strategy suitable for the synthesis of the triene component of the oxazolomycin antibioticsThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.
  作者：Paul G. Bulger、Mark G. Moloney、Paul C. Trippier

  DOI：10.1039/b306925g

  日期：——

  Concise and versatile routes suitable for the synthesis of three geometric isomers of an analogue of the left hand triene sub-unit of oxazolomycin are reported. A strategy based upon a key Heck reaction was unsuccessful, and this was traced to a combination of steric encumbrance and electronic deactivation of the alkene substrate. An alternative Stille coupling strategy, however, proved to be both versatile and high yielding, and is potentially applicable to the synthesis of analogues with variation both in the side-chain geometry and in the identity of the terminal aromatic or heteroaromatic residue.

  报道了适用于合成oxazolomycin左旋三烯子单元类似物的三种几何异构体的简明且多功能的路线。基于关键Heck反应的策略未能成功，这归因于烯烃底物的空间阻碍和电子失活。然而，另一种Stille偶联策略既多功能又高产，且有可能适用于合成侧链几何结构和末端芳香或杂芳香残基不同的类似物。