trans-1-Phenyl-2-trans-β-styrenylcyclopropane | 22467-90-9

• 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-1-Phenyl-2-trans-β-styrenylcyclopropane
• 英文别名: trans-1-phenyl-2-((E)-2-phenylethenyl)cyclopropane；trans-1-((E)-Styryl)-2-phenylcyclopropane；[(E)-2-[(1R,2S)-2-phenylcyclopropyl]ethenyl]benzene
• CAS: 22467-90-9；96094-89-2；149197-75-1
• 化学式: C₁₇H₁₆
• 分子量: 220.314
• InChiKey: LWOCZQGLJDAHIB-PUENXVRKSA-N

物化性质

• 沸点：
  345.2±22.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  trans-1-Phenyl-2-trans-β-styrenylcyclopropane 在 对苯二酚 作用下， 以 环己烷 为溶剂， 反应 3.0h， 生成 (3R,4S)-cis-3,4-diphenylcyclopentene 、 trans-3,4-Diphenylcyclopentene
  参考文献：
  名称：

  Quantitative Analyses of the Four Isomers of 3,4-Diphenylcyclopentene by Chiral Gas Chromatography

  摘要：

  The four isomers of 3,4-diphenylcyclopentene are well resolved by chiral gas chromatography on a Cyclodex B column, eluting in the ordered sequence (3S,4R), (3R,4S), (3S,4S), and(3R,4R). Absolute stereochemical assignments were made through chemical correlations relating the 3,4-diphenylcyclopentenes with a known reference compound, (1S,2S)-(+)-cis-2-phenylcyclopentanol.

  DOI：

  10.1021/jo00123a010
• 作为产物：
  描述：

  二氯甲烷 、 1,4-二苯基-1,3丁二烯 在 magnesium 作用下， 生成 trans-1-Phenyl-2-trans-β-styrenylcyclopropane
  参考文献：
  名称：

  Rieke 金属介导的 E,E-1,4-二苯基-1,3-丁二烯与二氯烷烃的碳环化反应

  摘要：

  摘要 钡和锶的 Rieke 金属配合物很容易与 E,E-1,4-二苯基-1,3-丁二烯反应形成金属-二烯试剂。在用l.n-二氯烷烃处理后，这些金属环以优异的化学产率转化为环衍生物。

  DOI：

  10.1080/00397919508011489

文献信息

• Organocalcium chemistry: preparation and reactions of highly reactive calcium
  作者：Tse Chong Wu、Heping Xiong、Reuben D. Rieke

  DOI：10.1021/jo00304a016

  日期：1990.8
• Chemistry of substituted (2-butene-1,4-diyl)magnesium: a facile approach to complex carbocycles, functionalized ketones and alcohols, and silicon-containing heterocycles
  作者：Reuben D. Rieke、Heping Xiong

  DOI：10.1021/jo00009a034

  日期：1991.4

  Highly reactive magnesium reacts with a wide variety of substituted 1,3-dienes to give the corresponding substituted (2-butene-1,4-diyl)magnesium complexes. Reactions of symmetrical (2-butene-1,4-diyl)magnesium with alpha,omega-alkylene dihalides form three-, four-, five-, and six-membered carbocycles. Significantly, the cyclizations are always stereospecific and completely regioselective. Depending on the initial 1,3-diene and specific electrophiles, uncyclized products can be obtained. Stepwise reactions of (2,3-dimethyl-2-butene-1,4-diyl)magnesium with two different electrophiles afford polyfunctionalized ketones with the generation of a quaternary center. Formal 1,2-additions can be effected in this manner. Substituted five- and six-membered cyclic ketones can also be synthesized in one step by this approach. Treatment of unsymmetrical (2-butene-1,4-diyl)magnesium complexes with triorganosilyl chlorides followed by cyclohexanone results in additions across a terminal double bond with high regioselectivity. Silicon-containing heterocycles or spiro compounds can be readily synthesized by using the bis-Grignard reagents.
• Asuncion, Lisa A.; Baldwin, John E., Journal of the American Chemical Society, 1995, vol. 117, # 43, p. 10672 - 10677
  作者：Asuncion, Lisa A.、Baldwin, John E.

  DOI：——

  日期：——