(S)-1-(2-furyl)ethyl benzoate | 201279-57-4

• 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: (S)-1-(2-furyl)ethyl benzoate
• 英文别名: (S)-(-)-2-(1-benzoyloxyethyl)furan；(S)-benzoic acid 1-furan-2-yl-ethyl ester；[(1S)-1-(furan-2-yl)ethyl] benzoate
• CAS: 201279-57-4
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: HTAHCYJKGQIYMR-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-二溴-3-戊酮 、 (S)-1-(2-furyl)ethyl benzoate 在 锌铜偶 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以100%的产率得到(1'R)-1-(2,4-dimethyl-3-oxo-8-oxabicyclo[3.2.1]oct-6-en-1-yl)ethyl benzoate
  参考文献：
  名称：

  Asymmetry induction on the [4C(4π)+3C(2π)] cycloaddition reaction of C2-functionalized furans: influence of the chiral auxiliary nature

  摘要：

  The study of the pi-facial diastereoselectivity in the [4+3] cycloaddition reaction of thirteen different chiral 2-substituted furans with oxyallyl cations, under sonochemical and/or thermal conditions, is presented. In almost all studied furans, a cis diastereoselectivity and a high endo diastereoselectivity is observed. Decreasing the distance between the closest stereocenter of the chiral auxiliary and the reactive C2-carbon of the furan ring, increases the pi-facial diastereoselectivity, especially by using chiral furyl-sulfoxides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00452-0
• 作为产物：
  描述：

  (S)-1-(2-furanyl)ethanol 、 1-benzoyl-1,2,4-triazole 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (S)-1-(2-furyl)ethyl benzoate
  参考文献：
  名称：

  The configurational assignment of the optically active 5-(1-hydro-peoxyethyl)-3-ethoxycarbonyl-2-methylfuran and its alcohol by exciton-coupled circular dichroism (ECCD)

  摘要：

  The absolute configuration of the furan-derived hydroperoxide land its alcohol 2, readily available in optically active form by kinetic resolution of the racemic hydroperoxide with horseradish peroxidase (HRP), was determined by the exciton-coupled circular dichroism (ECCD) method on their 2-naphthoate derivatives 4. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00515-6

文献信息

• Optically active cantharidin analogues possessing selective inhibitory activity on Ser/Thr protein phosphatase 2B (calcineurin): Implications for the binding mode
  作者：Yoshiyasu Baba、Nozomu Hirukawa、Mikiko Sodeoka

  DOI：10.1016/j.bmc.2005.05.013

  日期：2005.9

  serine/threonine protein phosphatase 1 and 2A (PP1 and PP2A) inhibitor, with less potent inhibitory activity for PP2B, which regulates T-cell proliferation. We synthesized and evaluated four optically pure stereoisomers of 1-substituted norcantharidin analogues. The absolute stereochemistry of each stereoisomer was determined based on X-ray crystal structure analysis. Remarkably, optically active cantharidin

  Cantharidin众所周知是一种有效的丝氨酸/苏氨酸蛋白磷酸酶1和2A（PP1和PP2A）抑制剂，对PP2B的抑制作用较弱，后者可调节T细胞增殖。我们合成并评估了1个取代的胭脂红素类似物的四种光学纯立体异构体。基于X射线晶体结构分析确定每种立体异构体的绝对立体化学。显着地，具有（1S）-构型的旋光邻苯二酚类似物显示出对PP2B的选择性抑制，而不抑制PP1或PP2A。
• Induction of asymmetry on the [4+3] cycloaddition reaction of C2-functionalized furans
  作者：Angel M Montaña、Pedro M Grima

  DOI：10.1016/s0040-4039(02)00199-5

  日期：2002.3

  A study of the induction of asymmetry on the [4+3] cycloaddition reaction of some 13 C2-substituted furan derivatives with 2-oxyallyl cation is presented. The asymmetry was induced by a chiral auxiliary on C2 of furan. A vis diastereospecificity and a high endo diastereoselectivity are observed in almost all studied cases. On decreasing the distance between the stereocenter of the chiral auxiliary and the reactive C2-carbon of the furan ring, the pi-facial diastereoselectivity is increased. especially by using chiral furyl-sulfoxides. (C) 2002 Elsevier Science Ltd. All rights reserved.