(2S,3S)-2,3-diphenylcyclopentan-1-one | 64154-47-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2S,3S)-2,3-diphenylcyclopentan-1-one
• CAS: 64154-47-8
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: XQOVPZAXALWHAL-NVXWUHKLSA-N

物化性质

• 熔点：
  98 °C
• 沸点：
  371.7±42.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,3-diphenylcyclopentan-1-one 在 盐酸 、 amalgamated zinc 作用下， 生成 trans-1,2-Diphenyl-cyclopentan
  参考文献：
  名称：

  128.循环系统中的阴离子和质子性变化。第六部分 顺-和反式-3：4二苯基环戊酮。4 -二苯基- Δ：通过还原2-羟基- 3得到的酮的结构2 -环pentenone与氢碘酸

  摘要：

  DOI：

  10.1039/jr9390000567
• 作为产物：
  描述：

  3,4-二苯基环戊烯 在 lithium aluminium tetrahydride 、 Celite 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 (2S,3S)-2,3-diphenylcyclopentan-1-one
  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

文献信息

• Diastereoselective Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to α-Substituted Cyclic Enones
  作者：Ang Gao、Xiu-Yan Liu、Chang-Hua Ding、Xue-Long Hou

  DOI：10.1055/s-0036-1590742

  日期：2017.12

  A palladium-catalyzed conjugate addition of arylboronic acids to α-substituted cyclic enones was developed to give α,β-disubstituted ketones with high diastereoselectivity. Mechanistic investigation showed that the high diastereoselectivity was realized through epimerization.

  开发了钯催化的芳基硼酸与 α-取代环烯酮的共轭加成，以得到具有高非对映选择性的 α,β-二取代酮。机理研究表明，高非对映选择性是通过差向异构化实现的。
• Weidlich; Meyer-Delius, Chemische Berichte, 1941, vol. 74, p. 1195,1209
  作者：Weidlich、Meyer-Delius

  DOI：——

  日期：——
• Ring expansion of cyclobutanones to cyclopentanones via .alpha.-lithioalkyl aryl sulfoxides and selenoxides
  作者：Robert C. Gadwood、Ishwar M. Mallick、Amy J. DeWinter

  DOI：10.1021/jo00381a013

  日期：1987.3
• Asymmetric Carbon−Carbon Bond Formations by Conjugate Additions of Lithiated <i>N</i>-Boc Allylic Amines to Nitroalkenes:  Enantioselective Synthesis of Functionalized Cyclopentanoids
  作者：Timothy A. Johnson、Michael D. Curtis、Peter Beak

  DOI：10.1021/ol026277g

  日期：2002.8.1

  [GRAPHICS]Allylic organolithiums generated by enantioselective deprotonation of N-Boc-N-(p-methoxyphenyl) allylic amines undergo conjugate additions with nitroalkenes to provide enecarbamates containing two contiguous stereogenic centers in good yields with high diastereoselectivities and enantioselectivities. Further elaboration of these adducts to enantioenriched substituted cyclopentanones and aminocyclopentanes is reported.
• 128. Anionotropic and prototropic changes in cyclic systems. Part VI. cis- and trans-3 : 4-Diphenylcyclopentanones. The structure of the ketone obtained by reduction of 2-hydroxy-3 : 4-diphenyl-Δ²-cyclopentenone with hydriodic acid
  作者：Harold Burton、Charles W. Shoppee

  DOI：10.1039/jr9390000567

  日期：——