(E)-2-methyl-4-oxobut-2-enyl benzoate | 155093-61-1

• 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)-2-methyl-4-oxobut-2-enyl benzoate
• 英文别名: [(E)-2-methyl-4-oxobut-2-enyl] benzoate
• CAS: 155093-61-1
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: JQPKXNJDXXJLJD-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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)-2-methyl-4-oxobut-2-enyl benzoate 、 (4S,5S)-5-((E)-5-Chloro-3-methyl-pent-3-enyl)-1-iodo-4-isopropyl-5-methyl-cyclopentene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 Benzoic acid (E)-4-[(4R,5R)-5-((E)-5-chloro-3-methyl-pent-3-enyl)-4-isopropyl-5-methyl-cyclopent-1-enyl]-4-hydroxy-2-methyl-but-2-enyl ester
  参考文献：
  名称：

  dolabellanes的有效合成。

  摘要：

  通过α-磺酰基碳负离子与α，β-不饱和醛的分子内缩合制备了十一元碳环。脱磺酰化提供了以[9.3.0]环十四烷骨架为特征的烯丙基醇的高效立体控制合成，该骨架表征了多兰烷二萜。

  DOI：

  10.1016/s0040-4039(00)61504-6
• 作为产物：
  描述：

  在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以39%的产率得到(E)-2-methyl-4-oxobut-2-enyl benzoate
  参考文献：
  名称：

  Alkyne-Enol Ether Cross-Metathesis in the Presence of CuSO₄: Direct Formation of 3-Substituted Crotonaldehydes in Aqueous Medium

  摘要：

  An efficient synthesis of 3-substituted crotonaldehydes via alkyne-enol ether cross-metathesis in the presence of CuSO4 and in aqueous medium was developed. Crotonaldehydes were obtained in good yields from terminal aryl-alkynes as well as from terminal alkyl-alkynes. All of the reactions were carried out under microwave irradiation and were completed in a few minutes. Water was used as the cosolvent, making c, this approach safer, economic, and desiderable from an enviromental point of view.

  DOI：

  10.1021/jo900205x

文献信息

• Asymmetric Diels-Alder Reaction of α-Substituted and β,β-Disubstituted α,β-Enals via Diarylprolinol Silyl Ether for the Construction of All-Carbon Quaternary Stereocenters
  作者：Yujiro Hayashi、Bojan P. Bondzic、Tatsuya Yamazaki、Yogesh Gupta、Shin Ogasawara、Tohru Taniguchi、Kenji Monde

  DOI：10.1002/chem.201602345

  日期：2016.10.24

  Diels–Alder reaction of α‐substituted acrolein proceeds in the presence of the trifluoroacetic acid salt of trifluoromethyl‐substituted diarylprolinol silyl ether to afford the exo‐isomer with both excellent diastereoselectivity and high enantioselectivity. In the Diels–Alder reaction of a β,β‐disubstituted α,β‐unsaturated aldehyde, good exo‐selectivity and excellent enantioselectivity was obtained when the

  α-取代的丙烯醛的不对称Diels-Alder反应在三氟甲基取代的二芳基脯氨醇甲硅烷基醚的三氟乙酸盐存在下进行，从而提供具有优异的非对映选择性和高对映选择性的外向异构体。在β，β-二取代的α，β-不饱和醛的Diels-Alder反应中，当将三氟甲基取代的二芳基脯氨醇的大体积三异丙基甲硅烷基醚的高氯酸盐用作有机催化剂时，可获得良好的exo-选择性和出色的对映选择性。水的存在。在这两种情况下，全碳四元立体中心都是对映选择性地构建的。
• An efficient synthesis of the dolabellanes.
  作者：David R. Williams、Paul J. Coleman、C.Richard Nevill、Leslie A. Robinson

  DOI：10.1016/s0040-4039(00)61504-6

  日期：1993.12

  intramolecular condensations of α-sulfonyl carbanions with α,β-unsaturated aldehydes. Desulfonylation provides an efficient stereocontrolled synthesis of allylic alcohols featuring the [9.3.0] cyclotetradecane skeleton which characterizes the dolabellane diterpenes.

  通过α-磺酰基碳负离子与α，β-不饱和醛的分子内缩合制备了十一元碳环。脱磺酰化提供了以[9.3.0]环十四烷骨架为特征的烯丙基醇的高效立体控制合成，该骨架表征了多兰烷二萜。
• Alkyne-Enol Ether Cross-Metathesis in the Presence of CuSO₄: Direct Formation of 3-Substituted Crotonaldehydes in Aqueous Medium
  作者：Daniele Castagnolo、Lorenzo Botta、Maurizio Botta

  DOI：10.1021/jo900205x

  日期：2009.4.17

  An efficient synthesis of 3-substituted crotonaldehydes via alkyne-enol ether cross-metathesis in the presence of CuSO4 and in aqueous medium was developed. Crotonaldehydes were obtained in good yields from terminal aryl-alkynes as well as from terminal alkyl-alkynes. All of the reactions were carried out under microwave irradiation and were completed in a few minutes. Water was used as the cosolvent, making c, this approach safer, economic, and desiderable from an enviromental point of view.