trans-2-phenyl-trans-3-vinyl-1-(methoxycarbonyl)cyclopropane

• 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: trans-2-phenyl-trans-3-vinyl-1-(methoxycarbonyl)cyclopropane
• 英文别名: trans-2-phenyl-cis-3-vinyl-1-(methoxycarbonyl)cyclopropane；Methyl 2-ethenyl-3-phenylcyclopropane-1-carboxylate
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: AEAACQUYISQCGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-(S)-2-((S)-Hydroxy-phenyl-methyl)-5-tributylstannanyl-pent-3-enoic acid methyl ester 在 苯膦酰二氯 、 三乙胺 作用下， 反应 15.0h， 以77%的产率得到trans-2-phenyl-trans-3-vinyl-1-(methoxycarbonyl)cyclopropane
  参考文献：
  名称：

  Original Synthesis of 1,2-Oxathiolan-2-oxides and Vinyl Cyclopropane Carboxylic Esters

  摘要：

  1,2-氧硫杂环戊烷-2-氧化物或乙烯基环丙烷羧酸酯是以 2,4-戊二烯酸甲酯、三丁基斯坦尼锂和羰基化合物为原料，通过化学选择性制备而成，而且产量相当高。在制备过程中，后者会正式脱氧，并扮演碳烯化合物的角色。

  DOI：

  10.1055/s-1997-6140

文献信息

• Diastereoselective Synthesis of Vinylcyclopropanes from Dienes and Sulfur Ylides
  作者：Raphaël Robiette、Jacqueline Marchand-Brynaert

  DOI：10.1055/s-2008-1032080

  日期：——

  The reaction of aryl- and vinyl-stabilized sulfonium ylides with electron-poor dienes has been investigated. Clean cyclopropanation to 2-aryl- and 2-vinyl-substituted vinylcyclopropanes, with high regio- and stereocontrol, was observed. This new diastereoselective strategy was applied to formal synthesis of lamoxirene and dictyopterene B.

  研究了芳基和乙烯基稳定锍酰化物与贫电子二烯的反应。观察到了 2-芳基和 2-乙烯基取代的乙烯基环丙烷的清洁环丙烷化反应，并且具有高度的区域和立体控制。这一新的非对映选择性策略被应用于正式合成拉莫塞烯烃和双蝶烯 B。
• Cyclopropanation Reactions of Allylic Ylides with α,β-Unsaturated Esters and Amides:  Tuning of Stereoselectivity and the Dramatic Effect of Lithium Salts
  作者：Yong Tang、Yao-Zeng Huang、Li-Xin Dai、Zheng-Fa Chi、Li-Ping Shi

  DOI：10.1021/jo960063t

  日期：1996.1.1

  The allylic telluronium ylides 2a-2c, generated in situ from the corresponding telluronium salts 1a-1c in the presence of a lithium salt, reacted with alpha,beta-unsaturated esters or amides to afford trans-2-vinyl-trans-3-substituted cyclopropyl esters or amides, respectively, with high selectivity and generally excellent yields. in the absence of lithium salts, the stereoselectivity of these reactions changed to give cis-2-vinyl-trans-3-substituted cyclopropyl esters or amides. The ratio of the two isomers 4 and 5 can be tuned from 99:1 to 1:99. Other factors, such as temperature, solvents, and amounts of base, are also shown to influence the stereochemistry of this reaction. mechanism for tuning of the reaction stereochemistry by simply varying reaction conditions is proposed.
• Original Synthesis of 1,2-Oxathiolan-2-oxides and Vinyl Cyclopropane Carboxylic Esters
  作者：Alain Krief、Laurent Provins

  DOI：10.1055/s-1997-6140

  日期：1997.6

  1,2-Oxathiolan-2-oxides or vinyl cyclopropane carboxylic esters are prepared chemoselectively and in rather good yields from methyl 2,4-pentadienoate, tributylstannyllithium and carbonyl compounds. The later are formally deoxygenated in the process and play the role of carbenes.

  1,2-氧硫杂环戊烷-2-氧化物或乙烯基环丙烷羧酸酯是以 2,4-戊二烯酸甲酯、三丁基斯坦尼锂和羰基化合物为原料，通过化学选择性制备而成，而且产量相当高。在制备过程中，后者会正式脱氧，并扮演碳烯化合物的角色。