Trifluoro-methanesulfonic acid 4-phenyl-but-2-ynyl ester | 252317-90-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Trifluoro-methanesulfonic acid 4-phenyl-but-2-ynyl ester
• 英文别名: 4-Phenylbut-2-ynyl trifluoromethanesulfonate；4-phenylbut-2-ynyl trifluoromethanesulfonate
• CAS: 252317-90-1
• 化学式: C₁₁H₉F₃O₃S
• 分子量: 278.252
• InChiKey: YECUUPMHXZEVHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid 4-phenyl-but-2-ynyl ester 在 5percent Pd/BaSO₄ 吡啶 、 喹啉 、 氢氟酸 、 甲基锂 、 氢气 作用下， 以 四氢呋喃 、 环己烷 、 乙腈 、 苯 为溶剂， -30.0~40.0 ℃ 、101.33 kPa 条件下， 反应 4.83h， 生成 (2R,3R,4R)-4-hydroxy-3-[(E)-oct-1-enyl]-2-[(Z)-4-phenylbut-2-enyl]cyclohexan-1-one
  参考文献：
  名称：

  Solution- and Soluble-Polymer Supported Asymmetric Syntheses of Six-Membered Ring Prostanoids

  摘要：

  An asymmetric synthesis of prostanoids containing a six-membered ring core structure (11a-homoprostaglandins), both in solution and using non-cross-linked polystyrene (NCPS) as a soluble support, was developed. Target molecule 1 was generated in a convergent fashion using a three-component coupling strategy, wherein chiral enone (R)-2 was the precursor of the central ring and the cuprate 3 and triflate 4 were used to introduce the side chains. The chiral center of (R)-2 directed the facial selectivity of the conjugate addition reaction which then dictated the stereochemical outcome of the subsequent alpha alkylation. Attachment of a six-membered ring scaffold to NCPS facilitated purification without compromising synthetic yields, still allowed H-1-NMR analysis of the intermediates in the synthesis, and provided an avenue for the construction of six-membered ring prostanoid libraries.

  DOI：

  10.1002/1521-3765(20000602)6:11<1917::aid-chem1917>3.0.co;2-7
• 作为产物：
  描述：

  三氟甲磺酸酐 、 4-phenyl-2-butyn-1-ol 在 2,6-二叔丁基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 Trifluoro-methanesulfonic acid 4-phenyl-but-2-ynyl ester
  参考文献：
  名称：

  可溶性聚合物支持的前列腺素类文库的合成：抗病毒活性的鉴定。

  摘要：

  前列腺素是有效的天然产物，参与许多生物过程。从类前列腺素组分的“工具箱”中“聚合产生多样性”，再加上其他聚合物支持的转化，可以构建有价值的文库。并行池策略用于组装小型前列腺素类库。疱疹家族病毒的抑制表明了发现新药的潜力。

  DOI：

  10.1021/ol991130j

文献信息

• Soluble-Polymer Supported Synthesis of a Prostanoid Library:  Identification of Antiviral Activity
  作者：Kyung Joo Lee、Ana Angulo、Peter Ghazal、Kim D. Janda

  DOI：10.1021/ol991130j

  日期：1999.12.1

  [formula: see text] The prostaglandins are potent natural products taking part in many biological processes. The "convergent generation of diversity" from a "toolbox" of prostanoid components, augmented with additional polymer-supported transformations, can enable construction of valuable libraries. A parallel-pool strategy was used to assemble a small library of prostanoids. The inhibition of a herpes-family

  前列腺素是有效的天然产物，参与许多生物过程。从类前列腺素组分的“工具箱”中“聚合产生多样性”，再加上其他聚合物支持的转化，可以构建有价值的文库。并行池策略用于组装小型前列腺素类库。疱疹家族病毒的抑制表明了发现新药的潜力。
• Solution- and Soluble-Polymer Supported Asymmetric Syntheses of Six-Membered Ring Prostanoids
  作者：José A. López-Pelegrín、Kim D. Janda

  DOI：10.1002/1521-3765(20000602)6:11<1917::aid-chem1917>3.0.co;2-7

  日期：2000.6.2

  An asymmetric synthesis of prostanoids containing a six-membered ring core structure (11a-homoprostaglandins), both in solution and using non-cross-linked polystyrene (NCPS) as a soluble support, was developed. Target molecule 1 was generated in a convergent fashion using a three-component coupling strategy, wherein chiral enone (R)-2 was the precursor of the central ring and the cuprate 3 and triflate 4 were used to introduce the side chains. The chiral center of (R)-2 directed the facial selectivity of the conjugate addition reaction which then dictated the stereochemical outcome of the subsequent alpha alkylation. Attachment of a six-membered ring scaffold to NCPS facilitated purification without compromising synthetic yields, still allowed H-1-NMR analysis of the intermediates in the synthesis, and provided an avenue for the construction of six-membered ring prostanoid libraries.