(R)-1-(p-tolyl)-1-pentyn-3-ol | 235431-02-4

• 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: (R)-1-(p-tolyl)-1-pentyn-3-ol
• 英文别名: (3R)-1-(4-methylphenyl)pent-1-yn-3-ol
• CAS: 235431-02-4
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: CPHZFKQTWUHGLL-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 (R)-1-(p-tolyl)-1-pentyn-3-ol 在 氢气 、 1,4-双(二苯基膦)丁烷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (S)-(+)-incrustoporin 、 (R)-incrustoporin
  参考文献：
  名称：

  Enantioselective synthesis of (R)-incrustoporin, an antibiotic isolated from Incrustoporia carneola

  摘要：

  Highly enantiomerically enriched (R)-incrustoporin was enantioselectively synthesized in 43.6% overall yield starting from 4-iodotoluene. The key steps of the synthesis included the asymmetric hydrogenation of 1-(p-tolyl)-1-pentyn-3-one catalyzed by a non-racemic Ru(II) complex and the Pd-catalyzed cyclocarbonylation of so-obtained highly enantiomerically enriched 1-(p-tolyl)-1-pentyn-3-ol. This Pd-catalyzed reaction, whose stereochemical outcome was previously unknown, proceeded with retention of configuration and 2.5% or less racemization. The enantiomeric purities of (R)-1-(p-tolyl)-1-pentyn-3-ol and (R)-incrustoporin were evaluated by HPLC analysis on a Chiralcel OJ column as well as by performing the H-1 NMR spectra of these compounds in a D2O solution which was saturated with alpha- or beta-cyclodextrin, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00085-3
• 作为产物：
  描述：

  1-(p-tolyl)pent-1-yn-3-one 在 氢氧化钾 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 (1R,2R)-(-)-N-(对甲基苯磺酰基)-1,2-二苯基乙二胺 作用下， 以 异丙醇 为溶剂， 反应 4.5h， 以86.2%的产率得到(R)-1-(p-tolyl)-1-pentyn-3-ol
  参考文献：
  名称：

  Enantioselective synthesis of (R)-incrustoporin, an antibiotic isolated from Incrustoporia carneola

  摘要：

  Highly enantiomerically enriched (R)-incrustoporin was enantioselectively synthesized in 43.6% overall yield starting from 4-iodotoluene. The key steps of the synthesis included the asymmetric hydrogenation of 1-(p-tolyl)-1-pentyn-3-one catalyzed by a non-racemic Ru(II) complex and the Pd-catalyzed cyclocarbonylation of so-obtained highly enantiomerically enriched 1-(p-tolyl)-1-pentyn-3-ol. This Pd-catalyzed reaction, whose stereochemical outcome was previously unknown, proceeded with retention of configuration and 2.5% or less racemization. The enantiomeric purities of (R)-1-(p-tolyl)-1-pentyn-3-ol and (R)-incrustoporin were evaluated by HPLC analysis on a Chiralcel OJ column as well as by performing the H-1 NMR spectra of these compounds in a D2O solution which was saturated with alpha- or beta-cyclodextrin, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00085-3

文献信息

• Enantioselective synthesis of (R)-incrustoporin, an antibiotic isolated from Incrustoporia carneola
  作者：Renzo Rossi、Fabio Bellina、Matteo Biagetti、Luisa Mannina

  DOI：10.1016/s0957-4166(99)00085-3

  日期：1999.3

  Highly enantiomerically enriched (R)-incrustoporin was enantioselectively synthesized in 43.6% overall yield starting from 4-iodotoluene. The key steps of the synthesis included the asymmetric hydrogenation of 1-(p-tolyl)-1-pentyn-3-one catalyzed by a non-racemic Ru(II) complex and the Pd-catalyzed cyclocarbonylation of so-obtained highly enantiomerically enriched 1-(p-tolyl)-1-pentyn-3-ol. This Pd-catalyzed reaction, whose stereochemical outcome was previously unknown, proceeded with retention of configuration and 2.5% or less racemization. The enantiomeric purities of (R)-1-(p-tolyl)-1-pentyn-3-ol and (R)-incrustoporin were evaluated by HPLC analysis on a Chiralcel OJ column as well as by performing the H-1 NMR spectra of these compounds in a D2O solution which was saturated with alpha- or beta-cyclodextrin, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.