(E)-3-((2RS,3RS)-3-phenyloxiran-2-yl)prop-2-en-1-ol | 136590-84-6

• 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: (E)-3-((2RS,3RS)-3-phenyloxiran-2-yl)prop-2-en-1-ol
• 英文别名: (E)-3-[(2R,3R)-3-phenyloxiran-2-yl]prop-2-en-1-ol
• CAS: 136590-84-6；136657-48-2
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: OWJSMDMMMRAWBC-OZSGMGSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  32.76
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-3-((2RS,3RS)-3-phenyloxiran-2-yl)prop-2-en-1-ol 在 碳酸氢钠 、 三苯基膦 作用下， 以 四氯化碳 为溶剂， 生成 (2R,3R)-2-((E)-3-Chloro-propenyl)-3-phenyl-oxirane
  参考文献：
  名称：

  A highly efficient practical method for the synthesis of chiral polyhydroxy-(E,E)-1-chlorodienols and (E)-5-hydroxy enynes

  摘要：

  An efficient protocol for the synthesis of chiral polyhydroxy-(E, E)-1-chlorodienols and (E)-5-hydroxy enynes from chiral 4,5-epoxy trans allyl chlorides and 4,5-O-isopropylidene allyl chlorides is described by using stoichiometric amount of LiNH2 or LDA in HMPA : THF (1 : 5) useful in the synthesis of biologically active natural products. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00907-6
• 作为产物：
  描述：

  (E)-3-((2S,3S)-3-Phenyl-oxiranyl)-propenal 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 生成 (E)-3-((2RS,3RS)-3-phenyloxiran-2-yl)prop-2-en-1-ol
  参考文献：
  名称：

  A highly efficient practical method for the synthesis of chiral polyhydroxy-(E,E)-1-chlorodienols and (E)-5-hydroxy enynes

  摘要：

  An efficient protocol for the synthesis of chiral polyhydroxy-(E, E)-1-chlorodienols and (E)-5-hydroxy enynes from chiral 4,5-epoxy trans allyl chlorides and 4,5-O-isopropylidene allyl chlorides is described by using stoichiometric amount of LiNH2 or LDA in HMPA : THF (1 : 5) useful in the synthesis of biologically active natural products. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00907-6

文献信息

• An Atom-Economic Synthesis of Bicyclo[3.1.0]hexanes by Rhodium N-Heterocyclic Carbene-Catalyzed Diastereoselective Tandem Hetero-[5 + 2] Cycloaddition/Claisen Rearrangement Reaction of Vinylic Oxiranes with Alkynes
  作者：Jian-Jun Feng、Junliang Zhang

  DOI：10.1021/ja2014604

  日期：2011.5.18

  The first synthetic application of a vinylic oxirane as a heteroatom-containing five-atom component in transition-metal-catalyzed cycloaddition reactions is reported. A new, efficient, diastereoselective tandem intramolecular hetero-[5+2] cycloaddition/Claisen rearrangement of vinylic oxirane-alkyne substrates that uses a rhodium NHC complex and provides strategically novel, atom-economic, regiospecific

  报道了乙烯基环氧乙烷作为含杂原子的五原子组分在过渡金属催化的环加成反应中的首次合成应用。一种新的、有效的、非对映选择性串联分子内杂-[5+2] 环加成/克莱森重排乙烯基环氧乙烷-炔底物，它使用铑 NHC 复合物并提供战略性的新颖、原子经济、区域特异性和非对映选择性访问 [3.1.0 ] 双环产品已开发完成。
• Highly stereoselective one-step synthesis of 5-aryl- and 5-(2-styrenyl)-4,5-trans-epoxy-2(E)-pentenols employing an arsonium salt
  作者：Wei-Bo Wang、Li-Lan Shi、Zbi-Qun Li、Yao-Zeng Huang

  DOI：10.1016/0040-4039(91)80610-i

  日期：1991.8

  5-Aryl- and 5-(2-styrenyl)-4,5-trans-epoxy-2E-penten-l-ols were conveniently synthesized by a one-step reaction of aldehydes with arsonium salt 2b under mild conditions (rt, KF.Al2O3, phase transfer).