1-[(4-methylphenyl)sulfonyl]-4-(1-phenylethenyl)-3-pyrrolidinol

• 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-[(4-methylphenyl)sulfonyl]-4-(1-phenylethenyl)-3-pyrrolidinol
• 英文别名: cis-4-(1-phenylvinyl)-1-(toluene-4-sulfonyl)pyrrolidin-3-ol；4-(1-phenyl-vinyl)-1-(toluene-4-sulfonyl)pyrrolidin-3-ol；(3S,4S)-1-(4-methylphenyl)sulfonyl-4-(1-phenylethenyl)pyrrolidin-3-ol
• 化学式: C₁₉H₂₁NO₃S
• 分子量: 343.447
• InChiKey: RDJBDJHTFROMMJ-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-methylbenzenesulfonamide 在 4-二甲氨基吡啶 、 双(1,2-双(二苯基膦)乙烷)钯 、 四丁基氟化铵 、 sodium hydride 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 magnesium 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 26.0h， 生成 1-[(4-methylphenyl)sulfonyl]-4-(1-phenylethenyl)-3-pyrrolidinol
  参考文献：
  名称：

  Asymmetric palladium-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant

  摘要：

  使用甲酸作还原剂的不对称钯/手性二膦催化的烯丙基醋酸酯-醛反向环化反应可得到顺式-二取代吡咯烷、四氢呋喃和螺环碳骨架。

  DOI：

  10.1039/c5cc02176f

文献信息

• cis-Stereoselective nickel-catalyzed cyclization/alkylation and arylation reactions of allenyl-aldehydes and -ketones with organozinc reagentsElectronic supplementary information (ESI) available: typical procedures, NMR-data, and X-ray data. See http://www.rsc.org/suppdata/cc/b2/b207620a/
  作者：Suk-Ku Kang、Seok-Keun Yoon

  DOI：10.1039/b207620a

  日期：2002.11.4

  Highly stereoselective alkylative and arylative cyclization reactions of allenyl-aldehydes and -ketones with organozinc reagents occur efficiently in the presence of catalytic Ni(COD)2 to afford cis-fused homoallylic cyclopentanols.

  在催化Ni（COD）2的存在下，烯丙基-醛和-酮与有机锌试剂的高度立体选择性烷基化和芳基化环化反应可有效发生，以提供顺式稠合均烯丙基环戊醇。
• Key Factors for High Diastereo- and Enantioselectivity of Umpolung Cyclizations of Aldehyde-Containing Allylpalladium Intermediates
  作者：Hirokazu Tsukamoto、Ayumu Kawase、Hirotaka Omura、Takayuki Doi

  DOI：10.1246/bcsj.20190167

  日期：2019.10.15

  Two palladium/chiral diphosphine-catalyzed umpolung cyclizations of aldehyde-containing allylic acetates and allenes with arylboronic acid are fully investigated to establish key factors in their h...

  充分研究了两种钯/手性二膦催化的含醛乙酸烯丙酯和丙二烯与芳基硼酸的 umpolung 环化反应，以确定其反应的关键因素。
• Enantioselective Arylative Cyclization of Allenyl Aldehydes with Arylboronic Acids under Pd(II)-diphosphine Catalysis
  作者：Hirokazu Tsukamoto、Tomotaka Matsumoto、Yoshinori Kondo

  DOI：10.1021/ol702966j

  日期：2008.3.1

  A Pd(OAc)(2)-SEGPHOS combination catalyzes the first enantioselective arylative cyclization of allenyl aldehydes with arylboronic acids to provide cis-fused five- and six-membered cyclic homoallylic alcohols. The excellent diastereo- and enantioselectivity and the fact that the reaction proceeds at room temperature in the absence of any additives make the process highly practical.
• Palladium-Catalyzed Tandem Cyclization of Allenyl-Aldehydes and -Ketones with Aryl Iodides and Bu₃SnSnBu₃
  作者：Young-Hwan Ha、Suk-Ku Kang

  DOI：10.1021/ol025557t

  日期：2002.4.1

  [GRAPHICS]The arylative cyclization of allenyl-aidehydes with aryl iodides and hexa-n-butyldistannane to form substituted cyclopentanols and cyclohexanols by tandem palladium-catalyzed carbostannylation and allylation was achieved under mild conditions.
• Palladium−Indium-Mediated Arylative Cyclization of Allenyl-Aldehydes and -Ketones
  作者：Suk-Ku Kang、Sung-Won Lee、Jihyun Jung、Yoongho Lim

  DOI：10.1021/jo020017v

  日期：2002.6.1

  The arylative cyclization of allenyl-aldehydes and -ketones to form homoallylic cyclopentanols and cyclohexanols by the palladium-catalyzed and indium-mediated Babier allylation is described.