1-(phenylsulfonyl)cyclopentene | 64740-90-5

• 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: 1-(phenylsulfonyl)cyclopentene
• 英文别名: (1-Cyclopenten-1-ylsulfonyl)benzene；cyclopenten-1-ylsulfonylbenzene
• CAS: 64740-90-5
• 化学式: C₁₁H₁₂O₂S
• 分子量: 208.281
• InChiKey: ARNVQXOIPFIQMR-UHFFFAOYSA-N

物化性质

• 熔点：
  20-25 °C
• 沸点：
  382.9±25.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(phenylsulfonyl)cyclopentene 在 lithium diphenyl cuprate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以90%的产率得到((2-phenylcyclopentyl)sulfonyl)benzene
  参考文献：
  名称：

  Amine-directed addition of cuprate reagents to cyclopentenyl sulfones

  摘要：

  DOI：

  10.1016/s0040-4039(00)84276-8
• 作为产物：
  描述：

  (+/-)-trans-1-benzenesulfonyl-2-chloro-cyclopentane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 1-(phenylsulfonyl)cyclopentene
  参考文献：
  名称：

  Chlorosulfenylation-dehydrochlorination reactions. New and improved methodology for the synthesis of unsaturated aryl sulfides and aryl sulfones

  摘要：

  DOI：

  10.1021/jo00400a041

文献信息

• The arenesulphonomercuriation of alkenes—a route to vinyl sulphones
  作者：Wojciech Sas

  DOI：10.1039/c39840000862

  日期：——

  Vinyl sulphones were obtained from the reaction of alkenes with mercury(II) chloride and sodium arenesulphinate followed by base catalysed eliminative demercuriation.

  乙烯砜是由烯烃与氯化汞（II）和苯磺酸钠的反应，然后经碱催化的消除脱汞反应制得的。
• A Tin-Free, Radical Photocatalyzed Addition to Vinyl Sulfones
  作者：Davide Ravelli、Sara Montanaro、Michele Zema、Maurizio Fagnoni、Angelo Albini

  DOI：10.1002/adsc.201100591

  日期：2011.12

  Radical conjugate addition onto vinyl sulfones was achieved by means of a convenient, tin-free procedure. This was based on the photocatalyzed CH bond activation in aldehydes, amides, ethers and even cycloalkanes by using tetrabutylammonium decatungstate (TBADT). The reaction was likewise effective for the functionalization of β-substituted vinyl sulfones. The products are useful building blocks and

  通过方便的无锡方法将自由基共轭物加成到乙烯基砜上。这是基于使用四丁基癸酸铵（TBADT）在醛，酰胺，醚甚至环烷烃中的光催化CH键活化。该反应对于β-取代的乙烯基砜的官能化同样有效。该产品是有用的结构单元，在人造紫外线和日光下均能以令人满意的收率获得，因此证明了该工艺的“绿色”潜力。
• Iodosulfonation of alkenes with benzenesulfinic acid – <i>N</i>-iodosuccinimide — Facile preparation of α,β-unsaturated sulfones
  作者：Russell R Wolff、Vikram Basava、Robert M Giuliano、Walter J Boyko、J Herman Schauble

  DOI：10.1139/v06-051

  日期：2006.4.1

  Reaction of alkenes and alkenols with N-iodosuccinimide (NIS) and benzenesulfinic acid in dichloromethane at room temperature affords vic-iodophenylsulfonyl adducts in good to high yields. Treatment of the iodosulfones with neutral alumina in dichloromethane at room temperature results in dehydroiodination to give the corresponding vinyl sulfones in high yield and purity by this convenient two-step procedure. Application of the iodosulfonation–dehydroiodination sequence to allylic alcohols and silyl ethers gave γ-oxygenated, α,β-unsaturated phenylsulfones, while the attempted iodosulfonation of glycals, as intermediates to vinyl sulfones, resulted in addition of benzenesulfinic acid with double bond shift (Ferrier rearrangement). Key words: iodosulfonation, vinyl sulfones, benzenesulfinic acid, N-iodosuccinimide, dehydroiodination.

  室温下，烯和烯醇与 N-iodosuccinimide (NIS) 和苯亚磺酸在二氯甲烷中发生反应，生成的邻碘苯磺酰基加合物收率高。在室温下，用中性氧化铝在二氯甲烷中处理碘砜，然后进行脱氢碘化，通过这种简便的两步法得到相应的乙烯基砜，收率和纯度都很高。将碘磺化脱氢碘化顺序应用于烯丙基醇和硅基醚，可得到γ-氧合的、α,β-不饱和的苯基砜，而尝试对作为乙烯基砜中间体的甘油进行碘磺化，则会导致苯亚磺酸的加成和双键转移（费里尔重排）。关键词：碘磺化、乙烯基砜、苯亚磺酸、N-碘代丁二酰亚胺、脱氢碘化。
• Phosphazene base P2-Et mediated isomerization of vinyl sulfones to allyl sulfones
  作者：Zhendong Jin、Seong Heon Kim、P.L. Fuchs

  DOI：10.1016/0040-4039(96)01110-0

  日期：1996.7

  Treatment of vinyl sulfones with 0.1–0.2 eq of Phosphazene base, P2-Et in THF at 25°C affords the corresponding allyl sulfones in high yield. P2-Et has shown clear superiority to both DBU and KO-t-Bu in these reactions.

  在25°C的条件下，用THF中的0.1–0.2当量的磷腈碱，P 2 -Et处理乙烯基砜，可以得到相应的烯丙基砜。在这些反应中，P 2 -Et已显示出明显优于DBU和KO-t-Bu的优势。
• A New c<i>ine</i>-Substitution of Alkenyl Sulfones with Aryltitanium Reagents Catalyzed by Rhodium:  Mechanistic Studies and Catalytic Asymmetric Synthesis of Allylarenes
  作者：Kazuhiro Yoshida、Tamio Hayashi

  DOI：10.1021/ja0295568

  日期：2003.3.1

  The reaction of alkenyl sulfones with aryltitanium triisopropoxide (ArTi(OPr-i )3) in the presence of 3 mol % of [Rh(OH)((S)-binap)]2 in THF at 40 degrees C gave high yield of cine-substitution products. The catalytic cycle was established by deuterium-labeling studies, and it was applied to catalytic asymmetric synthesis of allylarenes which proceeds with over 99% enantioselectivity.

  烯基砜与芳基三异丙醇钛 (ArTi(OPr-i )3) 在 3 mol% [Rh(OH)((S)-binap)]2 的 THF 存在下在 40°C 下反应，得到高产率的电影——替代产品。通过氘标记研究建立了催化循环，并将其应用于烯丙基芳烃的催化不对称合成，其对映选择性超过 99%。