ethyl (2R)-2-((2R,3S,5R)-2-allyl-5-phenyltetrahydrofuran-3-yl)-2-hydroxypropanoate | 1041081-72-4

• 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: ethyl (2R)-2-((2R,3S,5R)-2-allyl-5-phenyltetrahydrofuran-3-yl)-2-hydroxypropanoate
• 英文别名: ethyl (2R)-2-hydroxy-2-[(2R,3S,5R)-5-phenyl-2-prop-2-enyloxolan-3-yl]propanoate
• CAS: 1041081-72-4
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: ZUEZCIPKAQPIIV-BVIKNXMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2R)-2-((2R,3S,5R)-2-allyl-5-phenyltetrahydrofuran-3-yl)-2-hydroxypropanoate 、 乙酸酐 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以80%的产率得到(2R,3S,4R)-1-ethoxy-2-methyl-1-oxo-3-styrylhept-6-ene-2,4-diyl diacetate
  参考文献：
  名称：

  Asymmetric multicomponent reactions: convenient access to acyclic stereocenters and functionalized cyclopentenoids

  摘要：

  Asymmetric multicomponent reactions of optically active phenyl dihydrofuran, keto ester or N-tosyl imino ester, and allylsilane provided functionalized phenyl tetrahydrofurans with multiple stereogenic centers diastereoselectively. Cleavage of the resulting substituted tetrahydrofurans readily provided acyclic derivatives with three contiguous asymmetric centers via an acyloxycarbenium ion intermediate. Ring closing olefin metathesis, using Grubbs catalyst, afforded functionalized cyclopentene derivatives in optically active form. A one-pot tandem tetrahydrofuran ring cleavage followed by ring closing olefin metathesis also provided functionalized cyclopentenes in good yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.005
• 作为产物：
  描述：

  丙酮酸乙酯 、 呋喃,2,3-二氢-2-苯基-,(R)- 、 烯丙基三甲基硅烷 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到ethyl (2R)-2-((2R,3S,5R)-2-allyl-5-phenyltetrahydrofuran-3-yl)-2-hydroxypropanoate
  参考文献：
  名称：

  Asymmetric multicomponent reactions: convenient access to acyclic stereocenters and functionalized cyclopentenoids

  摘要：

  Asymmetric multicomponent reactions of optically active phenyl dihydrofuran, keto ester or N-tosyl imino ester, and allylsilane provided functionalized phenyl tetrahydrofurans with multiple stereogenic centers diastereoselectively. Cleavage of the resulting substituted tetrahydrofurans readily provided acyclic derivatives with three contiguous asymmetric centers via an acyloxycarbenium ion intermediate. Ring closing olefin metathesis, using Grubbs catalyst, afforded functionalized cyclopentene derivatives in optically active form. A one-pot tandem tetrahydrofuran ring cleavage followed by ring closing olefin metathesis also provided functionalized cyclopentenes in good yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.005

文献信息

• Asymmetric multicomponent reactions: convenient access to acyclic stereocenters and functionalized cyclopentenoids
  作者：Arun K. Ghosh、Sarang S. Kulkarni、Chun-Xiao Xu、Khriesto Shurrush

  DOI：10.1016/j.tetasy.2008.04.005

  日期：2008.5

  Asymmetric multicomponent reactions of optically active phenyl dihydrofuran, keto ester or N-tosyl imino ester, and allylsilane provided functionalized phenyl tetrahydrofurans with multiple stereogenic centers diastereoselectively. Cleavage of the resulting substituted tetrahydrofurans readily provided acyclic derivatives with three contiguous asymmetric centers via an acyloxycarbenium ion intermediate. Ring closing olefin metathesis, using Grubbs catalyst, afforded functionalized cyclopentene derivatives in optically active form. A one-pot tandem tetrahydrofuran ring cleavage followed by ring closing olefin metathesis also provided functionalized cyclopentenes in good yield. (C) 2008 Elsevier Ltd. All rights reserved.