4-hydroxy-6-pentyl-δ-lactone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-hydroxy-6-pentyl-δ-lactone
• 英文别名: 3-hydroxy-5-decanolide；2H-pyran-2-one,tetrahydro-4-hydroxy-6-pentyl-；tetrahydro-4-hydroxy-6-pentyl-2H-pyran-2-one；2H-Pyran-2-one, tetrahydro-4-hydroxy-6-pentyl-；4-hydroxy-6-pentyloxan-2-one
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: WPOYJLMQCBFDQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 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

• 作为产物：
  描述：

  4-[2-(tert-Butyl-dimethyl-silanyloxy)-heptyl]-oxetan-2-one 在 氢氟酸 作用下， 以 乙腈 为溶剂， 以60%的产率得到4-hydroxy-6-pentyl-δ-lactone
  参考文献：
  名称：

  Fournier, Lycia; Gaudel-Siri, Anouk; Kocieński, Philip J., Synlett, 2003, # 1, p. 107 - 111

  摘要：

  DOI：

文献信息

• Substituted 3-hydroxy-delta-lactones from epoxides
  申请人：Coates Geoffrey W.

  公开号：US20100145046A1

  公开（公告）日：2010-06-10

  Catalysts and methods for the carbonylation of epoxides to substituted 3-hydroxy-δ-lactones and β-lactones are disclosed.

  揭示了用于将环氧化合物羰基化为取代的3-羟基-δ-内酯和β-内酯的催化剂和方法。
• SUBSTITUTED 3-HYDROXY-DELTA-LACTONES FROM EPOXIDES
  申请人：Cornell University

  公开号：US20140107339A1

  公开（公告）日：2014-04-17

  Catalysts and methods for the carbonylation of epoxides to substituted 3-hydroxy-δ-lactones and β-lactones are disclosed.

  本发明揭示了催化剂和方法，用于将环氧化合物羰基化为取代的3-羟基-δ-内酯和β-内酯。
• Method for producing lactones from a strain of Aureobasidium pullulans
  申请人：CHARABOT

  公开号：US10196659B2

  公开（公告）日：2019-02-05

  The invention relates to a method for producing lactones from a strain of Aureobasidium pullulans that are produced from a pre-culture of the Aureobasidium pullulans strain CBS 771.97, obtained from CBS-KNAW Fungal Biodiversity Center, Uppsalalaan 8, 3584 CT Utrecht, Netherlands, or related strains; from an inoculum obtained from the pre-culture; a culture is produced by fermentation at a temperature between 20° C. and 40° C. over a period of at least 3 days so as to produce metabolites, in a sterilized aqueous production medium containing: a carbon source; a nitrogen source; a mineral salt solution; and a calcium source, at a concentration between 2 and 100 mM; and following the fermentation period, converting the metabolites produced into a lactone mixture comprising (R)-5,6-dihydro-6-pentyl-2H-pyran-2-one (or (R)-(−)-massoia lactone) and/or (4R,6R)-4-hydroxy-6-pentyl-tetrahydro-2H-pyran-2-one.

  本发明涉及一种从Aureobasidium pullulans菌株中生产内酯的方法，该菌株是从CBS-KNAW真菌生物多样性中心，Uppsalalaan 8，3584 CT Utrecht，Netherlands获得的Aureobasidium pullulans菌株CBS 771.97或相关菌株的预培养物中产生的；从预培养物中获得的接种体；在20℃至40℃的温度下发酵产生培养物。在灭菌的含水生产培养基中发酵至少 3 天，以产生代谢物，该培养基含有碳源、氮源、矿物盐溶液和钙源，浓度在 2 至 100 mM 之间；发酵期结束后，将产生的代谢物转化为内酯混合物，其中包括 (R)-5,6-二氢-6-戊基-2H-吡喃-2-酮（或 (R)-(-)-马索内酯）和/或 (4R,6R)-4-羟基-6-戊基-四氢-2H-吡喃-2-酮。
• Carbonylation of Epoxides to Substituted 3-Hydroxy-δ-Lactones
  作者：John W. Kramer、Daniel Y. Joh、Geoffrey W. Coates

  DOI：10.1021/ol702475e

  日期：2007.12.1

  Substituted 3-hydroxy-delta-lactones (3HLs) are valuable intermediates in the synthesis of pharmaceuticals and other biologically active-natural products. Herein we report the first example of the catalytic carbonylation of substituted homoglycidols to 3HLs using HCo(CO)(4). Upon optimization of the catalyst and reaction conditions, a functionally diverse set of 3HLs was prepared. Mechanistic insight was gained by observation of the carbonylation reaction using in situ IR spectroscopy, and we propose a mechanism that is consistent with previously studied epoxide carbonylation systems.
• PROCÉDÉ DE PRODUCTION DE LACTONES A PARTIR D'UNE SOUCHE D'AUREOBASIDIUM PULLULANS
  申请人：Charabot

  公开号：EP3110957A1

  公开（公告）日：2017-01-04