<(ethoxythiocarbonyl)sulfanyl>(hept-4(Z)-enyloxy)acetic acid methyl ester | 161254-26-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: <(ethoxythiocarbonyl)sulfanyl>(hept-4(Z)-enyloxy)acetic acid methyl ester
• 英文别名: methyl 2-ethoxycarbothioylsulfanyl-2-[(Z)-hept-4-enoxy]acetate
• CAS: 161254-26-8
• 化学式: C₁₃H₂₂O₄S₂
• 分子量: 306.447
• InChiKey: UILSDIRRGCXXIJ-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  <(ethoxythiocarbonyl)sulfanyl>(hept-4(Z)-enyloxy)acetic acid methyl ester 在 (t-BuO)2 作用下， 以 various solvent(s) 为溶剂， 反应 0.5h， 生成 (2R*,3R*)-3-<1-<(ethoxythiocarbonyl)sulfanyl>propyl>tetrahydropyran-2-carboxylic acid methyl ester 、 (2R*,3S*)-3-<1-<(ethoxythiocarbonyl)sulfanyl>propyl>tetrahydropyran-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：

  hept-4(Z)-enenitrile 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 乙酰氯 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 38.33h， 生成 <(ethoxythiocarbonyl)sulfanyl>(hept-4(Z)-enyloxy)acetic 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

• 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.