4-[(2R)-2-(furan-3-yl)-2-hydroxy-ethyl]-1,5-dioxa-spiro[5.5]undec-3-en-2-one | 212969-18-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(2R)-2-(furan-3-yl)-2-hydroxy-ethyl]-1,5-dioxa-spiro[5.5]undec-3-en-2-one
• 英文别名: 2-[(2R)-2-(furan-3-yl)-2-hydroxyethyl]-1,5-dioxaspiro[5.5]undec-2-en-4-one
• CAS: 212969-18-1
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: GDWYGYVOSAUUNW-CYBMUJFWSA-N

物化性质

• 沸点：
  374.113±41.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.287±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(2R)-2-(furan-3-yl)-2-hydroxy-ethyl]-1,5-dioxa-spiro[5.5]undec-3-en-2-one 在 sodium hydroxide 、 sodium tetrahydroborate 、 二乙基甲氧基硼烷 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 0.25h， 生成 (3S,5R)-5-(furan-3-yl)-3,5-dihydroxypentanoic acid
  参考文献：
  名称：

  An easy approach to chiral non-racemic 6-(furan-3-yl)-5,6-dihydro-pyran-2-ones

  摘要：

  Chiral non-racemic 6-(furan-3-yl)-pyran-2-one derivatives, key-intermediates in the preparation of compactin, manoalide and cacospongionolide subunits, are easily accessible through a rapid and convenient six-step sequence. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00210-9
• 作为产物：
  描述：

  3-糠醛 、 硅烷,三甲基[(4-亚甲基-1,5-二氧杂螺[5.5]十一碳-2-烯-2-基)氧代]- 在 titanium(IV) isopropylate 、 (R)-1,1'-Bi-2-naphthol 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到4-[(2R)-2-(furan-3-yl)-2-hydroxy-ethyl]-1,5-dioxa-spiro[5.5]undec-3-en-2-one
  参考文献：
  名称：

  A convenient catalytic procedure for the highly enantioselective aldol condensation of O-silyldienolates

  摘要：

  In the presence of catalytic amount of chiral Ti(OiPr)(4)/BINOL (0.08 equiv.) the asymmetric aldol condensation of 6-methyl-4H-[1,3]-dioxin-4-one-derived silyloxydienes takes place in high yields and enantiomeric excesses with aromatic. heteroaromatic, Unsaturated and aliphatic aldehydes. Notable amplification of enantiomeric excesses have been obtained by using enantioenriched catalytic systems. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00494-4

文献信息

• Enantioselective Synthesis of Pyranofuranone Moieties of Manoalide and Cacospongionolide B by Enzymatic and Chemical Approach
  作者：Margherita De Rosa、Annunziata Soriente、Guido Sodano、Arrigo Scettri

  DOI：10.1016/s0040-4020(00)00122-8

  日期：2000.3

  Two synthetic sequences leading to the pyranofuranone moieties of Manoalide and Cacospongionolide B in enantiomerically enriched forms are reported. The key steps involve either an enantioselective aldol condensation or an enzymatic resolution.

  报道了导致对映异构体富集形式的Manoalide和Cacospongionolide B的吡喃呋喃酮部分的两个合成序列。关键步骤涉及对映选择性羟醛缩合或酶促拆分。
• Enantioselective aldol condensation of O-silyl dienolates to aldehydes mediated by chiral BINOL–titanium complexes
  作者：Margherita De Rosa、Annunziata Soriente、Arrigo Scettri

  DOI：10.1016/s0957-4166(00)00259-7

  日期：2000.8

  Chiral BINOL-titanium complexes have been shown to catalyze enantioselective aldol reactions between dioxinone derivatives and a set of aldehydes. The aldol adducts are isolated in good yields and high enantioselectivities. A range of substitution patterns on the O-silyl dienolate is possible: alkyl and benzyl substituents are tolerated. A simple reaction protocol is described and provides an efficient alternative to the well-known methods for conducting enantioselective Mukaiyama aldol reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Efficient synthesis of chiral non-racemic 6-(furan-3-yl)-5,6-dihydro-pyran-2-ones
  作者：Margherita De Rosa、Rosanna Dell'Aglio、Annunziata Soriente、Arrigo Scettri

  DOI：10.1016/s0957-4166(99)00396-1

  日期：1999.9

  The title compounds are accessible in high yields and enantioselectivities by a five-step sequence involving in the key-step asymmetric aldol condensations of masked acetoacetic esters to 3-formyl furan. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A convenient catalytic procedure for the highly enantioselective aldol condensation of O-silyldienolates
  作者：Margherita De Rosa、Maria Rosaria Acocella、Rosaria Villano、Annunziata Soriente、Arrigo Scettri

  DOI：10.1016/s0957-4166(03)00494-4

  日期：2003.9

  In the presence of catalytic amount of chiral Ti(OiPr)(4)/BINOL (0.08 equiv.) the asymmetric aldol condensation of 6-methyl-4H-[1,3]-dioxin-4-one-derived silyloxydienes takes place in high yields and enantiomeric excesses with aromatic. heteroaromatic, Unsaturated and aliphatic aldehydes. Notable amplification of enantiomeric excesses have been obtained by using enantioenriched catalytic systems. (C) 2003 Elsevier Ltd. All rights reserved.
• An easy approach to chiral non-racemic 6-(furan-3-yl)-5,6-dihydro-pyran-2-ones
  作者：Annunziata Soriente、Margherita De Rosa、Patrizia Dovinola、Guido Sodano、Arrigo Scettri

  DOI：10.1016/s0957-4166(98)00210-9

  日期：1998.7

  Chiral non-racemic 6-(furan-3-yl)-pyran-2-one derivatives, key-intermediates in the preparation of compactin, manoalide and cacospongionolide subunits, are easily accessible through a rapid and convenient six-step sequence. (C) 1998 Elsevier Science Ltd. All rights reserved.