(E)-ethyl 2-(4-([1,1'-biphenyl]-4-yl)-6-(3-bromophenyl)-3,4-dihydro-2H-pyran-2-ylidene)acetate | 1336985-06-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (E)-ethyl 2-(4-([1,1'-biphenyl]-4-yl)-6-(3-bromophenyl)-3,4-dihydro-2H-pyran-2-ylidene)acetate
• 英文别名: ethyl (2E)-2-[(4S)-6-(3-bromophenyl)-4-(4-phenylphenyl)-3,4-dihydropyran-2-ylidene]acetate
• CAS: 1336985-06-8
• 化学式: C₂₇H₂₃BrO₃
• 分子量: 475.382
• InChiKey: JVNFDAYIGJQZFR-UPQSEYGOSA-N

物化性质

• 熔点：
  129 °C
• 沸点：
  606.0±55.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮乙酸乙酯 、 (E)-ethyl 2-(4-([1,1'-biphenyl]-4-yl)-6-(3-bromophenyl)-3,4-dihydro-2H-pyran-2-ylidene)acetate 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以74%的产率得到(E)-ethyl 2-(4-(4-bromophenyl)-6-(4-iodophenyl)-3,4-dihydro-2H-pyran-2-ylidene)acetate
  参考文献：
  名称：

  Development of a Formal Catalytic Asymmetric [4 + 2] Addition of Ethyl-2,3-butadienoate with Acyclic Enones

  摘要：

  Allene esters are unique not only as excellent electrophiles but also because of their ability for subsequent reactivity after the initial nucleophilic attack. A mechanistically inspired cyclization using ethyl-2,3-butadienoate and acyclic enones to provide dihydropyrans In excellent yields and enantioselectivity under solvent-free conditions at room temperature is reported.

  DOI：

  10.1021/ol202301f
• 作为产物：
  描述：

  3'-溴苯乙酮 在 hydroquinidine-9-phenanthryl ether 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 (E)-ethyl 2-(4-([1,1'-biphenyl]-4-yl)-6-(3-bromophenyl)-3,4-dihydro-2H-pyran-2-ylidene)acetate
  参考文献：
  名称：

  Development of a Formal Catalytic Asymmetric [4 + 2] Addition of Ethyl-2,3-butadienoate with Acyclic Enones

  摘要：

  Allene esters are unique not only as excellent electrophiles but also because of their ability for subsequent reactivity after the initial nucleophilic attack. A mechanistically inspired cyclization using ethyl-2,3-butadienoate and acyclic enones to provide dihydropyrans In excellent yields and enantioselectivity under solvent-free conditions at room temperature is reported.

  DOI：

  10.1021/ol202301f

文献信息

• Development of a Formal Catalytic Asymmetric [4 + 2] Addition of Ethyl-2,3-butadienoate with Acyclic Enones
  作者：Kumar Dilip Ashtekar、Richard J. Staples、Babak Borhan

  DOI：10.1021/ol202301f

  日期：2011.11.4

  Allene esters are unique not only as excellent electrophiles but also because of their ability for subsequent reactivity after the initial nucleophilic attack. A mechanistically inspired cyclization using ethyl-2,3-butadienoate and acyclic enones to provide dihydropyrans In excellent yields and enantioselectivity under solvent-free conditions at room temperature is reported.