6-[(2S)-2-(furan-3-yl)-2-hydroxyethyl]-2,2-dimethyl-1,3-dioxin-4-one | 212969-22-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-[(2S)-2-(furan-3-yl)-2-hydroxyethyl]-2,2-dimethyl-1,3-dioxin-4-one
• CAS: 212969-22-7
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: MKYUIJHGKMSMNW-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  6-[(2S)-2-(furan-3-yl)-2-hydroxyethyl]-2,2-dimethyl-1,3-dioxin-4-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
  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 、 (2,2-dimethyl-6-methylene-6H-1,3-dioxin-4-yloxy)trimethylsilane 在 titanium(IV) isopropylate 、 3 A molecular sieve 、 S-1,1'-联-2-萘酚 作用下， 以 四氢呋喃 为溶剂， 生成 6-[(2S)-2-(furan-3-yl)-2-hydroxyethyl]-2,2-dimethyl-1,3-dioxin-4-one 、 6-[(2R)-2-(furan-3-yl)-2-hydroxy-ethyl]-2,2-dimethyl-1,3-dioxin-4-one
  参考文献：
  名称：

  酶和化学方法对映选择性地合成Manoalide和Cacospongionolide B的吡喃呋喃酮部分

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(00)00122-8

文献信息

• First enantioselective synthesis of manoalide: application of aldehyde–dioxinone enantioselective condensation
  作者：Annunziata Soriente、Margherita De Rosa、Aniello Apicella、Arrigo Scettri、Guido Sodano

  DOI：10.1016/s0957-4166(99)00529-7

  日期：1999.12

  Manoalide, an analgesic and anti-inflammatory sesterterpene, has been stereoselectively synthesized for the first time. The C-4 stereogenic centre has been introduced in an early step by enantioselective aldol condensation using a Ti(OiPr)4/(R)-(+)-binol complex.

  Manoalide是一种止痛和消炎性的酯基萜烯，是首次立体选择性地合成的。C-4立体生成中心已通过使用Ti（O i Pr）4 /（R）-（+）-二元醇复合物的对映选择性羟醛缩合在较早的阶段引入。
• 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.