(R)-(+)-4-hydroxyphenyloxirane | 1176829-46-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (R)-(+)-4-hydroxyphenyloxirane
• 英文别名: (R)-(+)-4-hydroxystyrene oxide；4-[(2R)-oxiran-2-yl]phenol
• CAS: 1176829-46-1
• 化学式: C₈H₈O₂
• 分子量: 136.15
• InChiKey: BZENRVUXKMEUBO-QMMMGPOBSA-N

物化性质

• 沸点：
  275.5±28.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-乙酰氧基苯乙烯 在 调呋酸 、 水 、 过氧化脲素 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以78%的产率得到4-羟基苯乙烯
  参考文献：
  名称：

  Exploration of chiral induction on epoxides in lipase-catalyzed epoxidation of alkenes using (2R,3S,4R,5S)-(–)-2,3:4,6-di-O-isopropylidiene-2-keto-l-gulonic acid monohydrate

  摘要：

  Epoxidation of alkenes by peracid, generated in situ from (2R,3S,4R,5S)-(-)-2,3:4,6-di-O-isopropylidiene-2-keto-L-gulonic acid monohydrate [(-)-DIKGA] and hydrogen peroxide by lipase catalysis induces chirality on the product epoxides with moderate to good enantioselectivity (35-71%). Alkoxy/aralkyloxy styrenes however did not undergo any epoxidation. (R)-(+)-4-Hydroxy styrene-7,8-oxide was formed and isolated with moderate enantiomeric excess (57%) but was found to have poor stability. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.001

文献信息

• Method of Inducing Chirality to Epoxides Using 2,3:4,6 di-O-isopropylidene-2-keto-L-gulonic Acid Monohydrate
  申请人：Goswami Amrit

  公开号：US20100136635A1

  公开（公告）日：2010-06-03

  The present invention relates to a recyclable method to prepare chirally pure epoxides directly from olefins using a novel chiral acid 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid monohydrate as chiral inducer and anhydrous hydrogen peroxide in the form of urea hydrogen peroxide adduct (UHP) as oxidant and lipase enzyme as catalyst. Under the influence of lipase, the chiral acid 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid monohydrate is converted to per-acid in situ by the oxidant urea hydrogen peroxide which in turn transfers oxygen to olefin inducing chirality to the product epoxide. Using this technique, important epoxide building blocks of different industrially important compounds can be prepared with good yield and moderate enantioselectivity. Chiral epoxidation of olefins with environment friendly catalytic system that can be recycled is highly desirable in the context of Green Chemistry for preparation of many industrially important compounds.

  本发明涉及一种可回收的方法，使用新型手性酸2,3:4,6-二-O-异丙基亚甲基-2-酮-L-古洛酸单水合物作为手性诱导剂，以尿素过氧化氢加合物（UHP）作为氧化剂，脂肪酶酶作为催化剂，直接从烯烃制备手性纯环氧化物。在脂肪酶的作用下，手性酸2,3:4,6-二-O-异丙基亚甲基-2-酮-L-古洛酸单水合物被氧化剂尿素过氧化氢原位转化为过氧化物，进而将氧转移给烯烃，诱导产物环氧化物的手性。使用这种技术，可以以良好的产率和适度的对映选择性制备不同工业重要化合物的重要环氧化物构建块。在绿色化学的背景下，使用可回收的环保催化体系进行烯烃的手性环氧化是非常理想的，以制备许多工业重要化合物。
• US8148118B2
  申请人：——

  公开号：US8148118B2

  公开（公告）日：2012-04-03
• Exploration of chiral induction on epoxides in lipase-catalyzed epoxidation of alkenes using (2R,3S,4R,5S)-(–)-2,3:4,6-di-O-isopropylidiene-2-keto-l-gulonic acid monohydrate
  作者：Kuladip Sarma、Amrit Goswami、Bhabesh C. Goswami

  DOI：10.1016/j.tetasy.2009.05.001

  日期：2009.6

  Epoxidation of alkenes by peracid, generated in situ from (2R,3S,4R,5S)-(-)-2,3:4,6-di-O-isopropylidiene-2-keto-L-gulonic acid monohydrate [(-)-DIKGA] and hydrogen peroxide by lipase catalysis induces chirality on the product epoxides with moderate to good enantioselectivity (35-71%). Alkoxy/aralkyloxy styrenes however did not undergo any epoxidation. (R)-(+)-4-Hydroxy styrene-7,8-oxide was formed and isolated with moderate enantiomeric excess (57%) but was found to have poor stability. (C) 2009 Elsevier Ltd. All rights reserved.