(2S,4S,5S)-4-hydroxy-5-pentyloxolane-2-carbaldehyde | 1146741-40-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5S)-4-hydroxy-5-pentyloxolane-2-carbaldehyde
• CAS: 1146741-40-3
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: WLNKYTTYAJFMLP-GUBZILKMSA-N

物化性质

• 沸点：
  310.7±42.0 °C(predicted)
• 密度：
  1.092±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4S,5S)-4-hydroxy-5-pentyloxolane-2-carbaldehyde 在 二异丁基氢化铝 作用下， 反应 2.0h， 以13 mg的产率得到
  参考文献：
  名称：

  An Expeditious Total Synthesis of Both Diastereoisomeric Lipid Dihydroxytetrahydrofurans from Notheia anomala

  摘要：

  Short, high yielding syntheses of both diastereomers of the naturally occurring oxylipids 1 and 2 using a combination of organocatalytic hydroxylation of an aldehyde, alkene cross metathesis, and palladium(0) catalyzed cyclization chemistry (six-step process) are reported. Furthermore, the influence of the catalyst on the cross metathesis reaction of the homoallylic 1,2-diol has been studied in detail.

  DOI：

  10.1021/ol300597u
• 作为产物：
  描述：

  (2S)-2-(2-methylanilino)oxyheptanal 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium periodate 、 四氧化锇 、 四(三苯基膦)钯 、 CeCl₃*LiCl 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 、 柠檬酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 27.5h， 生成 (2S,4S,5S)-4-hydroxy-5-pentyloxolane-2-carbaldehyde
  参考文献：
  名称：

  An Expeditious Total Synthesis of Both Diastereoisomeric Lipid Dihydroxytetrahydrofurans from Notheia anomala

  摘要：

  Short, high yielding syntheses of both diastereomers of the naturally occurring oxylipids 1 and 2 using a combination of organocatalytic hydroxylation of an aldehyde, alkene cross metathesis, and palladium(0) catalyzed cyclization chemistry (six-step process) are reported. Furthermore, the influence of the catalyst on the cross metathesis reaction of the homoallylic 1,2-diol has been studied in detail.

  DOI：

  10.1021/ol300597u

文献信息

• Development of a Concise and General Enantioselective Approach to 2,5-Disubstituted-3-hydroxytetrahydrofurans
  作者：Baldip Kang、Jeffrey Mowat、Thomas Pinter、Robert Britton

  DOI：10.1021/ol802711s

  日期：2009.4.16

  Concise syntheses of 2,5-disubstituted-3-hydroxytetrahydrofurans have been developed that provide access to each configurational isomer of this scaffold from a single aldol adduct. Application of these methods to the rapid preparation of (6S,7S,9S,10S)- and (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol, two structurally related marine epoxylipids, is reported.

  已经开发了2，5-二取代的-3-羟基四氢呋喃的简明合成方法，其提供了从单个羟醛加合物获得该支架的每个构型异构体的途径。这些方法在快速制备（6 S，7 S，9 S，10 S）-和（6 S，7 S，9 R，10 R）-6,9-epoxynonadec-18-ene-7，中的应用据报道10-二醇是两种与结构相关的海洋环氧脂质。
• Protecting-group-directed stereodivergent Tsuji–Trost cyclization: total synthesis of oxylipids and (+)-petromyroxol
  作者：Rodney A. Fernandes、Dnyaneshwar A. Gorve、Amit K. Jha

  DOI：10.1039/d2cc04579f

  日期：——

  A stereodivergent protecting-group-directed Tsuji–Trost cyclization for efficient synthesis of both 2,5-cis- and 2,5-trans-disubstituted-THF scaffolds has been realized. The presence of a β-O-silyl group in allyl acetate results in cis-2,5-disubstituted-3-oxygenated THF in a good up to 9 : 1 dr. Alternatively, when the free OH at the β-position is available for acetate co-ordination, it gives a trans-2

  已经实现了立体发散保护基导向的 Tsuji-Trost 环化，可有效合成 2,5-顺式和 2,5-反式二取代-THF 支架。乙酸烯丙酯中β- O-甲硅烷基的存在导致顺式-2,5-二取代-3-氧化 THF 的比例高达 9:1 dr。或者，当 β 位的游离 OH 可用于乙酸酯配位时，它会产生反式-2,5-二取代-3-羟基 THF 支架，几乎是单一的非对映异构体（高达 1:0 dr）。合成的 THF 支架在氧脂和 (+)-petromyroxol 的全合成中进行。
• Inverse Temperature Dependence in the Diastereoselective Addition of Grignard Reagents to a Tetrahydrofurfural
  作者：Jeffrey Mowat、Baldip Kang、Branden Fonovic、Travis Dudding、Robert Britton

  DOI：10.1021/ol900324s

  日期：2009.5.21

  A remarkable example of inverse-temperature-dependent diastereoselectivity was uncovered while investigating the addition of Grignard reagents to a 3-hydroxytetrahydrofurfural. The free hydroxyl group in the tetrahydrofurfural was found to play a key role in these processes, a result corroborated through a series of DFT calculations that also highlighted an entropic preference for the formation of one diastereomer.