2-phenylsulfonyle hept-6-ynoate de methyle | 131190-11-9

• 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: 2-phenylsulfonyle hept-6-ynoate de methyle
• 英文别名: 6-Heptynoic acid, 2-(phenylsulfonyl)-, methyl ester；methyl 2-(benzenesulfonyl)hept-6-ynoate
• CAS: 131190-11-9
• 化学式: C₁₄H₁₆O₄S
• 分子量: 280.345
• InChiKey: PHYYLXWWVNBCJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenylsulfonyle hept-6-ynoate de methyle 在 盐酸 、 四氯化钛 、 三乙胺 作用下， 生成 1-(methoxycarbonyl)-1-(phenylsulfonyl)-2-methylenecyclopentane
  参考文献：
  名称：

  Intramolecular carbotitanation reaction of active methine compounds having an unactivated alkyne mediated by TiCl4Et3N

  摘要：

  In the presence of TiCl4 and Et3N, intramolecular carbotitanation reaction of active methine compounds having an unactivated 4-alkynyl group proceeds in a highly cis-selective manner to give methylenecyclopentane derivatives in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01579-2
• 作为产物：
  描述：

  pent-4-yn-1-yl methanesulfonate 、 α-phenylsulfonylmethylacetoacetate 生成 2-phenylsulfonyle hept-6-ynoate de methyle
  参考文献：
  名称：

  Stereospecific synthesis of arylidene and allylidene cyclopentanes by a palladium-catalyzed cylisation

  摘要：

  DOI：

  10.1016/s0040-4039(00)97827-4

文献信息

• Synthesis of ethynylidene cyclopentanes by a cyclisation catalyzed by the simultaneous presence of palladium (0) and copper (I)
  作者：Didier Bouyssi、Geneviève Balme、Jacques Gore

  DOI：10.1016/0040-4039(91)80215-r

  日期：1991.11

  Ethynylidene cyclopentanes can be formed in 35–71% yield from the reaction of the enolates of compounds such as δ-acetylenic malonates with 1-halogeno-1-alkynes. This reaction requires catalysis by both palladium (0) and copper (I) species.

  乙炔基丙二酸酯等化合物的烯醇化物与1-卤代-1-炔烃的反应可形成亚乙基环戊烷，产率为35-71％。该反应需要钯（0）和铜（I）物种的催化。
• An Efficient and General Microwave-Assisted Copper-Catalyzed Conia-Ene Reaction of Terminal and Internal Alkynes Tethered to a Wide Variety of Carbonucleophiles
  作者：Sonia Montel、Didier Bouyssi、Geneviève Balme

  DOI：10.1002/adsc.201000351

  日期：2010.9.10

  This paper describes a highly efficient, microwave‐assisted, Conia‐ene reaction of alkynes bearing a stabilizing carbon nucleophile. The reaction, catalyzed by a commercially available copper catalyst, proceeds under neutral conditions and is generally applicable even to less reactive nucleophiles such as malonate, cyanoacetate, and sulfonylacetate derivatives. This copper‐mediated cycloisomerization

  本文描述了带有稳定碳亲核试剂的炔烃的高效微波辅助的Conia-ene反应。由市售铜催化剂催化的反应在中性条件下进行，并且通常甚至适用于反应性较低的亲核试剂，如丙二酸酯，氰基乙酸酯和磺酰乙酸酯衍生物。这种铜介导的环异构化也适用于内部未活化的炔烃，仅导致相应的具有E烯烃化学性质的五元产物。
• Synthese de (e)-arylidene et allylidene cyclopentanes par une annelation catalysee par un complexe de palladium(0)
  作者：Guy Fournet、Geneviève Balme、Jacques Gore

  DOI：10.1016/s0040-4020(01)86561-3

  日期：1991.8

  When treated with an unsaturated halide in a palladium-catalyzed process, the anions from gamma-acetylenic malonates 4 and 5 stereospecifically lead to cyclopentanes having an exo tri- or tetra-substituted double bond. This reaction which forms simultaneously two carbon-carbon bonds is believed to proceed by nucleophilic attack of the anion on the triple bond activated by the sigma-aryl or sigma-vinyl palladium complex.
• Alkaline metallic reagent-catalyzed hydrocarbocyclization reaction ofvarious active methine compounds having an unactivated 4-alkynyl or allenyl group
  作者：Osamu Kitagawa、Takashi Suzuki、Hiroki Fujiwara、Masao Fujita、Takeo Taguchi

  DOI：10.1016/s0040-4039(99)00797-2

  日期：1999.6

  On using a catalytic amount of NaH or n-BuLi, hydrocarbocyclization;reaction of various active methine compounds having an unactivated 4-pentynyl or 3,4-pentadienyl group proceeded through proton transfer mechanism to give methylenecyclopentane derivatives in good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Carbocyclization Reaction of Active Methine Compounds with Unactivated Alkenyl or Alkynyl Groups Mediated by TiCl₄−Et₃N
  作者：Osamu Kitagawa、Takashi Suzuki、Tadashi Inoue、Yoko Watanabe、Takeo Taguchi

  DOI：10.1021/jo981603k

  日期：1998.12.1

  In the presence of TiCl4, Et3N, and I-2, iodocarbocyclization reaction of various active methine compounds having alkenyl groups gave iodocycloalkane derivatives in good yields. On the other hand, TiCl4 and Et3N promote the carbocyclization of active methine compounds with 4-alkynyl groups in the absence of I-2 to give methylenecyclopentane derivatives in good yields. This reaction proceeds with high streoselectivity through a cis-addition of trichlorotitanium enolates of active methine compounds to alkynes, and the resulting vinyltitanium intermediates can be further functionalized by the reaction with various electrophiles.