(S)-8-hydroxy-3-[(S)-2-hydroxypentyl]-6-methoxyisochroman-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (S)-8-hydroxy-3-[(S)-2-hydroxypentyl]-6-methoxyisochroman-1-one
• 英文别名: 7-deoxy-6-O-methylfusarentin；(3S)-8-hydroxy-3-[(2S)-2-hydroxypentyl]-6-methoxy-3,4-dihydroisochromen-1-one
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: PYCBCEHPDCTJMX-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-hydroxy-7-methoxy-2,2-dimethyl-benzo[1,3]dioxin-4-one 在 吡啶 、 四(三苯基膦)钯 、 氢气 、 palladium(II) hydroxide 、 magnesium oxide 、 四氯化钛 、 sodium hydride 、 臭氧 、 cesium fluoride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， -78.0~83.0 ℃ 、101.33 kPa 条件下， 反应 82.67h， 生成 (S)-8-hydroxy-3-[(S)-2-hydroxypentyl]-6-methoxyisochroman-1-one
  参考文献：
  名称：

  Total Synthesis of 7-Deoxy-6-O-methylfusarentin Featuring a Chelation-Controlled 1,3-Reetz–Keck-Type Allylation

  摘要：

  The total synthesis of 7-deoxy-6-O-methylfiisarentin (1) and a formal synthesis of 7-deoxy-6,8-O-dimethylfusarentin (2) has been successfully achieved in 10 steps. The described tactic underscores a diastereoselective strategy which incorporates a single acyclic reaction based on the initial stereocenter by means of a 1,3-chelation-controlled Reetz-Keck-type allylation.

  DOI：

  10.1021/jo301167a

文献信息

• Total synthesis of 7-desmethoxyfusarentin and its methyl ether
  作者：P. Janardhan Reddy、A. Srinivas Reddy、J.S. Yadav、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2012.05.059

  日期：2012.8

  A concise total synthesis of 7-desmethoxyfusarentin and its methyl ether has been accomplished involving a sequence of reactions such as Prins cyclization, ring opening of tetrahydropyran ring and Alder–Rickerts reaction as key steps. This is the first report on the construction of anti-1,3-diol unit of 7-desmethoxyfusarentin by means of Prins cyclization.

  简明的7-去甲氧基Fusarentin及其甲基醚的总合成已完成，其中涉及一系列反应，例如Prins环化，四氢吡喃环开环和Alder-Rickerts反应等关键步骤。这是关于通过Prins环化构建7-去甲氧基富沙伦汀的抗-1,3-二醇单元的第一份报道。
• Enantioselective synthesis of fusarentin methyl ethers: Insecticidal metabolites of Fusarium larvarum
  作者：Carole McNicholas、Thomas J. Simpson、Nicola J. Willett

  DOI：10.1016/0040-4039(96)01823-0

  日期：1996.10

  Fusarentin 4,5-dimethyl ether (1) and its 4-desmethoxy analogue are synthesised via acylation of the benzylic anion of N,N-dimethyl-2,3,4,-trimethoxy-6-methylbenzamide (9) and N,N-dimethyl-2,4-dimethoxy-6-methylbenzamide (8) with N-methoxy-N-methyl-(S)-3-tert-butyldimethylsilyloxyhexanamide (13): subsequent reduction of ketone (15) to the anti-1,3-diol (16) and acid catalysed cyclisation gives (1)

  Fusarentin 4,5-二甲基醚（1）及其4-去甲氧基类似物是通过N，N-二甲基-2,3,4，-三甲氧基-6-甲基苯甲酰胺（9）和N，N的苄基阴离子的酰化反应合成的-二甲基-2,4-二甲氧基-6-甲基苯甲酰胺（8）与N-甲氧基-N-甲基-（S）-3-叔丁基二甲基甲硅烷基氧己酰胺（13）：随后将酮（15）还原为抗-1， 3-二醇（16）和酸催化的环化得到（1）。
• Catalytic Enantioselective Synthesis of (<i>S</i>)-8-Hydroxy-3-[(<i>S</i>)-2′-hydroxypentyl]-6-methoxyisochroman-1-one, (<i>S</i>)-3-Hydroxy-3-[(<i>S</i>)-2′-hydroxypentyl]-6,8-dimethoxyisochroman-1-one, and Their Epimers
  作者：Gullapalli Kumaraswamy、Kukkadapu Ankamma、Nimmakayala Raghu、Dasa RamBabu

  DOI：10.1002/ejoc.201301708

  日期：2014.4

  The total synthesis of (S)-8-hydroxy-3-[(S)-2′-hydroxypentyl]-6-methoxyisochroman-1-one, (S)-3-hydroxy-3-[(S)-2′-hydroxypentyl]-6,8-dimethoxyisochroman-1-one, and their epimers has been successfully achieved. The key reactions include a catalytic enantioselective asymmetric epoxidation to introduce the chirality, and an Alder–Rickert reaction for the construction of the substituted phenyl ring.

  (S)-8-羟基-3-[(S)-2'-羟基戊基]-6-甲氧基异色满-1-one、(S)-3-羟基-3-[(S)-2'的全合成-羟基戊基]-6,8-二甲氧基异色满-1-one，其差向异构体已成功实现。关键反应包括催化对映选择性不对称环氧化以引入手性，以及用于构建取代苯环的 Alder-Rickert 反应。
• Total Synthesis of 7-Deoxy-6-<i>O</i>-methylfusarentin Featuring a Chelation-Controlled 1,3-Reetz–Keck-Type Allylation
  作者：Timothy N. Trotter、Aymara M. M. Albury、Michael P. Jennings

  DOI：10.1021/jo301167a

  日期：2012.9.7

  The total synthesis of 7-deoxy-6-O-methylfiisarentin (1) and a formal synthesis of 7-deoxy-6,8-O-dimethylfusarentin (2) has been successfully achieved in 10 steps. The described tactic underscores a diastereoselective strategy which incorporates a single acyclic reaction based on the initial stereocenter by means of a 1,3-chelation-controlled Reetz-Keck-type allylation.