bis((R)-1-methylpropyl) fumarate | 674784-75-9

• 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: bis((R)-1-methylpropyl) fumarate
• 英文别名: bis[(2R)-butan-2-yl] (E)-but-2-enedioate
• CAS: 674784-75-9
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: MWJNGKOBSUBRNM-WENXHQBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  顺式-二苯乙烯 、 bis((R)-1-methylpropyl) fumarate 以 甲苯 为溶剂， 生成 (1S,2S,3S,4S)-3,4-Diphenyl-cyclobutane-1,2-dicarboxylic acid bis-((R)-sec-butyl) ester 、 (1R,2R,3S,4S)-3,4-Diphenyl-cyclobutane-1,2-dicarboxylic acid bis-((R)-sec-butyl) ester 、 bis((R)-1-methylpropyl)δ-truxinate 、 bis((R)-1-methylpropyl)μ-truxinate
  参考文献：
  名称：

  Switching of Product's Chirality in Diastereodifferentiating [2+2] Photocycloaddition of (E)- versus (Z)-Stilbene to Chiral Fumarate upon Direct and Charge-Transfer-Band Excitation

  摘要：

  Diastereodifferentiating [2+2] photocycloadditions of (E)- and (Z)-stilbenes to bis((R)-1-methylpropyl) fumarate were performed through the direct excitation of stilbenes and the selective excitation of the charge-transfer (CT) complex at various temperatures. The geometrical isomers of stilbene afforded the opposite diastereomers of mu-truxinate in both excitation modes, with a dramatic decrease in the product's diastereoselectivity upon prolonged irradiations.

  DOI：

  10.1021/ol060468s
• 作为产物：
  描述：

  (R)-(-)-2-丁醇 、 反丁烯二酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以70%的产率得到bis((R)-1-methylpropyl) fumarate
  参考文献：
  名称：

  Diastereoselective [2 + 2] Photocycloaddition of Stilbene to Chiral Fumarate. Direct versus Charge-Transfer Excitation

  摘要：

  The selective excitation of the charge-transfer (CT) complex and the direct excitation of the substrate gave distinctly different product ratios and diastereomeric excesses (de's), as well as their temperature dependencies, in [2 + 2] photocycloaddition of (E)-stilbene to bis((R)-1-methylpropyl) fumarate, clearly demonstrating that the excited CT complex and the conventional exciplex differ in structure and reactivity. This conclusion is supported by the contrasting fluorescence behavior exhibited by the relevant excited species, particularly at low temperatures.

  DOI：

  10.1021/ja0370140

文献信息

• Diastereoselective [2 + 2] Photocycloaddition of Stilbene to Chiral Fumarate. Direct versus Charge-Transfer Excitation
  作者：Hideaki Saito、Tadashi Mori、Takehiko Wada、Yoshihisa Inoue

  DOI：10.1021/ja0370140

  日期：2004.2.1

  The selective excitation of the charge-transfer (CT) complex and the direct excitation of the substrate gave distinctly different product ratios and diastereomeric excesses (de's), as well as their temperature dependencies, in [2 + 2] photocycloaddition of (E)-stilbene to bis((R)-1-methylpropyl) fumarate, clearly demonstrating that the excited CT complex and the conventional exciplex differ in structure and reactivity. This conclusion is supported by the contrasting fluorescence behavior exhibited by the relevant excited species, particularly at low temperatures.
• Switching of Product's Chirality in Diastereodifferentiating [2+2] Photocycloaddition of (<i>E</i>)- versus (<i>Z</i>)-Stilbene to Chiral Fumarate upon Direct and Charge-Transfer-Band Excitation
  作者：Hideaki Saito、Tadashi Mori、Takehiko Wada、Yoshihisa Inoue

  DOI：10.1021/ol060468s

  日期：2006.4.1

  Diastereodifferentiating [2+2] photocycloadditions of (E)- and (Z)-stilbenes to bis((R)-1-methylpropyl) fumarate were performed through the direct excitation of stilbenes and the selective excitation of the charge-transfer (CT) complex at various temperatures. The geometrical isomers of stilbene afforded the opposite diastereomers of mu-truxinate in both excitation modes, with a dramatic decrease in the product's diastereoselectivity upon prolonged irradiations.