(1R,4S)-4-hydroxy-4-butyl-2-cyclopenten-1-yl acetate | 926920-38-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (1R,4S)-4-hydroxy-4-butyl-2-cyclopenten-1-yl acetate
• 英文别名: [(1R,4S)-4-butyl-4-hydroxycyclopent-2-en-1-yl] acetate
• CAS: 926920-38-9
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: GXQFJWQTJABSIW-WDEREUQCSA-N

物化性质

• 沸点：
  268.0±40.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4S)-4-hydroxy-4-butyl-2-cyclopenten-1-yl acetate 在 四(三苯基膦)钯 4-二甲氨基吡啶 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 (1S,5S)-7-butyl-4-(ethoxycarbonyl)-3-methyl-2-oxabicyclo[3.3.0]octa-3,7-diene
  参考文献：
  名称：

  Pd(0) catalyzed intramolecular alkylation: stereoselective synthesis of furan and isoxazoline-2-oxide analogs

  摘要：

  New optically pure isoxazoline-2-oxide and furan analogs have been synthesized using Pd(0) catalyzed intramolecular cyclizations. Starting from a meso-diol, optically pure compounds were prepared without utilizing chiral ligands at any stage of the synthesis. The stereochemical outcome of the product (> 99% ee) was influenced by desymmetrization catalyzed by Pseudomonas cepacia lipase and the stereoselective nature of the palladium catalyzed transformations. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.066
• 作为产物：
  描述：

  (1S,4R)-顺式-4-乙酰氧基-2-环戊烯-1-醇 在 4-二甲氨基吡啶 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1R,4S)-4-hydroxy-4-butyl-2-cyclopenten-1-yl acetate
  参考文献：
  名称：

  Pd(0) catalyzed intramolecular alkylation: stereoselective synthesis of furan and isoxazoline-2-oxide analogs

  摘要：

  New optically pure isoxazoline-2-oxide and furan analogs have been synthesized using Pd(0) catalyzed intramolecular cyclizations. Starting from a meso-diol, optically pure compounds were prepared without utilizing chiral ligands at any stage of the synthesis. The stereochemical outcome of the product (> 99% ee) was influenced by desymmetrization catalyzed by Pseudomonas cepacia lipase and the stereoselective nature of the palladium catalyzed transformations. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.066

文献信息

• ANTIVIRAL ACTIVITY OF CYCLOPENTENE NITRO-ESTER AND DERIVATIVES
  申请人：Bisht Kirpal S.

  公开号：US20100249230A1

  公开（公告）日：2010-09-30

  Disclosed is a method of synthesizing new optically pure heterocyclic compounds using Pd(0) catalyzed intramolecular cyclizations. Analogs of cyclopentanes, like isoxazoline-2-oxide and furan, with similar framework to the cyclopentanes act as anti-HIV and anticancer agents which opens a whole new field for application of these compounds. Starting from a meso-diol, optically pure compounds were prepared without utilizing chiral ligands at any stage of the synthesis. The stereochemical outcome of the product (>99% ee) was influenced by desymmetrization catalyzed by Pseudomonas cepacia lipase and the stereo selective nature of the palladium catalyzed transformations.

  本文介绍了一种使用Pd（0）催化的分子内环化合成新的光学纯杂环化合物的方法。类似于环戊烷的类似物，如异氧化异噁唑-2-氧化物和呋喃，具有与环戊烷类似的框架，作为抗HIV和抗癌剂，这为这些化合物的应用开辟了一个全新的领域。从meso-二醇开始，制备了光学纯化合物，而在合成的任何阶段都没有使用手性配体。产物的立体化学结果（> 99％ ee）受到Pseudomonas cepacialipase催化的去对称化和钯催化转化的立体选择性的影响。
• US8236853B1
  申请人：——

  公开号：US8236853B1

  公开（公告）日：2012-08-07
• US8318804B2
  申请人：——

  公开号：US8318804B2

  公开（公告）日：2012-11-27
• [EN] ANTIVIRAL ACTIVITY OF CYCLOPENTENE NITRO-ESTER AND DERIVATIVES<br/>[FR] ACTIVITÉ ANTIVIRALE DU NITRO-ESTER DE CYCLOPENTÈNE ET DE SES DÉRIVÉS
  申请人：UNIV SOUTH FLORIDA

  公开号：WO2009076397A2

  公开（公告）日：2009-06-18

  Disclosed is a method of synthesizing new optically pure heterocyclic compounds using Pd(0) catalyzed intramolecular cyclizations. Analogs of cyclopentanes, like isoxazoline-2-oxide and furan, with similar framework to the cyclopentanes act as anti-HIV and anticancer agents which opens a whole new field for application of these compounds. Starting from a meso-diol, optically pure compounds were prepared without utilizing chiral ligands at any stage of the synthesis. The stereochemical outcome of the product (>99% ee) was influenced by desymmetrization catalyzed by Pseudomonas cepacia lipase and the stereoselective nature of the palladium catalyzed transformations