acetoxy(pent-4-enyloxy)acetyc acid methyl ester | 251294-25-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: acetoxy(pent-4-enyloxy)acetyc acid methyl ester
• 英文别名: Methyl 2-acetyloxy-2-pent-4-enoxyacetate；methyl 2-acetyloxy-2-pent-4-enoxyacetate
• CAS: 251294-25-4
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: ZJLADDXUCLELBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  acetoxy(pent-4-enyloxy)acetyc acid methyl ester 在 盐酸 、 偶氮二异丁腈 、 二叔丁基过氧化物 、 三正丁基氢锡 、 乙酰氯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.83h， 生成 (2R*,3R*)-3-ethyltetrahydropyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Xanthate Transfer Cyclization of Glycolic Acid-Derived Radicals. Synthesis of Five- to Eight-Membered Ring Ethers

  摘要：

  A novel method for the preparation of functionalized five- to eight-membered ring ethers is described. This method involves the xanthate transfer radical cyclization of 2-(alken-1-oxy)-2-[(ethoxythio-carbonyl)sulfanyl]acetic acid methyl esters 6 to give good yields of xanthate-substituted five- to eight-membered ethers 7 and/or 8, depending on the length of the carbon chain. These cyclic ethers are usually obtained as mixtures of diastereomers. The cyclizations are performed at 150-160 degrees C in tert-butylbenzene with di-tert-butyl peroxide as the initiator. This group-transfer radical cyclization was successfully applied in a total synthesis of lauthisan (44). The use of benzoyl xanthate (56) as a catalyst allows a visible light-induced xanthate transfer cyclization to a tetrahydrofuran in high yield.

  DOI：

  10.1021/jo00101a027
• 作为产物：
  描述：

  4-戊烯-1-醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 acetoxy(pent-4-enyloxy)acetyc acid methyl ester
  参考文献：
  名称：

  Xanthate Transfer Cyclization of Glycolic Acid-Derived Radicals. Synthesis of Five- to Eight-Membered Ring Ethers

  摘要：

  A novel method for the preparation of functionalized five- to eight-membered ring ethers is described. This method involves the xanthate transfer radical cyclization of 2-(alken-1-oxy)-2-[(ethoxythio-carbonyl)sulfanyl]acetic acid methyl esters 6 to give good yields of xanthate-substituted five- to eight-membered ethers 7 and/or 8, depending on the length of the carbon chain. These cyclic ethers are usually obtained as mixtures of diastereomers. The cyclizations are performed at 150-160 degrees C in tert-butylbenzene with di-tert-butyl peroxide as the initiator. This group-transfer radical cyclization was successfully applied in a total synthesis of lauthisan (44). The use of benzoyl xanthate (56) as a catalyst allows a visible light-induced xanthate transfer cyclization to a tetrahydrofuran in high yield.

  DOI：

  10.1021/jo00101a027

文献信息

• Enzymatic resolution of α-acetoxyethers: A new approach to the synthesis of homochiral O,O-acetals
  作者：Sarah J. Fletcher、Christopher M. Rayner

  DOI：10.1016/s0040-4039(99)01483-5

  日期：1999.9

  A variety of alpha-acetoxyethers can be prepared by addition of an alcohol to a glyoxylate and ill situ acetylation using acetyl chloride. They can then be resolved using Pseudomonas fluorescens lipase. Selectivity is highly dependent on the substrate, with high enantiomeric excesses achieved in most cases, with some notable exceptions. Use of alternative lipase enzymes helps overcome such limitations. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Xanthate Transfer Cyclization of Glycolic Acid-Derived Radicals. Synthesis of Five- to Eight-Membered Ring Ethers
  作者：Jan H. Udding、J. P. M. Giesselink、Henk Hiemstra、W. Nico Speckamp

  DOI：10.1021/jo00101a027

  日期：1994.11

  A novel method for the preparation of functionalized five- to eight-membered ring ethers is described. This method involves the xanthate transfer radical cyclization of 2-(alken-1-oxy)-2-[(ethoxythio-carbonyl)sulfanyl]acetic acid methyl esters 6 to give good yields of xanthate-substituted five- to eight-membered ethers 7 and/or 8, depending on the length of the carbon chain. These cyclic ethers are usually obtained as mixtures of diastereomers. The cyclizations are performed at 150-160 degrees C in tert-butylbenzene with di-tert-butyl peroxide as the initiator. This group-transfer radical cyclization was successfully applied in a total synthesis of lauthisan (44). The use of benzoyl xanthate (56) as a catalyst allows a visible light-induced xanthate transfer cyclization to a tetrahydrofuran in high yield.