1-(1-乙氧基乙氧基)-4-碘丁烷 | 78647-37-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(1-乙氧基乙氧基)-4-碘丁烷
• 英文名称: tetramethylene iodohydrin EE ether
• 英文别名: 1-(1-ethoxyethoxy)-4-iodobutane；1-ethoxyethyl 4-iodobutyl ether
• CAS: 78647-37-7
• 化学式: C₈H₁₇IO₂
• 分子量: 272.126
• InChiKey: QPOZKZZFXOJASC-UHFFFAOYSA-N

物化性质

• 沸点：
  234.6±20.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(+)-3-(3',4'-isopropylidenedioxybutyl)-7,8-dimethyl-1,5-dihydro-2,4-benzodithiepin 、 1-(1-乙氧基乙氧基)-4-碘丁烷 生成 (4S)-4-[2-[3-[4-(1-ethoxyethoxy)butyl]-7,8-dimethyl-1,5-dihydro-2,4-benzodithiepin-3-yl]ethyl]-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  MORI, KENJI;WATANABE, HIDENORI, TETRAHEDRON LETT., 1984, 25, N 52, 6025-6026

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Chlor-3-(1'-aethoxyaethoxy)-butan 在 sodium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以60%的产率得到1-(1-乙氧基乙氧基)-4-碘丁烷
  参考文献：
  名称：

  α-乙酰内酯的合成；通过尝试直接环闭合获得 14 元双内酯

  摘要：

  α-乙酰内酯可通过向山-克莱森反应获得。通过 4-碘丁基乙酰乙酸酯的分子内烷基化或 2-烯丙基-3-氧代丁酸烯丙酯的烯烃复分解，尝试直接 7 元环闭合，仅提供二聚体 14 元环产物而不是预期的己内酯。

  DOI：

  10.1055/s-2002-31907

文献信息

• An important role played dianiones in the highly efficient macrocycle formation by an intramolecular alkyltion method: application to the synthesis of zearalenone
  作者：Takashi Takahashi、Toshiharu Nagashima、Hiroshi Ikeda、Jiro Tsuji

  DOI：10.1016/s0040-4039(00)85600-2

  日期：1982.1

  macrolides based on intramolecular alkylation of dianions, generated from phenylthiomethyl group and protected cyanohydrin, is reported. The use of dianions for the cyclization has several characteristics features; (1) Control of the conformation fo the side-chain, (2) Protection of the ester from a nucleophilic attack, (3) Acceleration of the intramolecular reaction without using high dilution conditions

  报道了一种新的合成方法，该方法基于苯硫基甲基和受保护的氰醇生成的基于阴离子的分子内烷基化的大环内酯。使用二价阴离子进行环化具有几个特征。（1）控制侧链的构象，（2）保护酯免受亲核攻击，（3）在不使用高稀释条件的情况下加速分子内反应。为了证明这些推测，使用二价阴离子的烷基化和在玉米赤霉烯酮的合成进行了研究。
• New synthetic method for orsellic acid type macrolides by intramolecular alkylation of protected cyanohydrin. The synthesis of (±)-zearalenone.
  作者：Takashi Takahashi、Hiroshi Ikeda、Jiro Tsuji

  DOI：10.1016/s0040-4039(01)90320-x

  日期：1981.1

  Zearalenone was synthesized by a general cyclization method of orsellic acid type macrolides having ketone moiety using the intramolecular alkylation of the protected cyanohydrin. This alkylation tolerates the presence of ester group and requires short reaction time.

  通过保护的氰醇的分子内烷基化，通过具有酮部分的奥索酸型大环内酯类的一般环化方法合成玉米赤霉烯酮。该烷基化耐受酯基的存在并且需要短的反应时间。
• Synthesis of α-Acetyl Lactones; Access to 14-Membered Bislactones by Attempts at Direct Ring Closure
  作者：Jens Christoffers、Heiko Oertling、Peter Fischer、Wolfgang Frey

  DOI：10.1055/s-2002-31907

  日期：——

  α-Acetyl lactones are accessed by Mukaiyama-Claisen reactions. Attempts at direct 7-membered ring closure, by either intramolecular alkylation of 4-iodobutyl acetoacetate or olefin metathesis from allyl 2-allyl-3-oxobutanoate, afford exclusively dimeric 14-membered ring products instead of the expected caprolactones.

  α-乙酰内酯可通过向山-克莱森反应获得。通过 4-碘丁基乙酰乙酸酯的分子内烷基化或 2-烯丙基-3-氧代丁酸烯丙酯的烯烃复分解，尝试直接 7 元环闭合，仅提供二聚体 14 元环产物而不是预期的己内酯。
• Synthesis of the enantiomers of 1,7-dioxaspiro[5.5]undecane and 4-hydroxy 1,7-dioxaspiro[5.5]undecane, the components of the olive fly pheromone
  作者：Kenji Mori、Uematsu Tamon、Watanabe Hidenori、Yanagi Kazunori、Minobet Masao

  DOI：10.1016/s0040-4039(01)91192-x

  日期：1984.1

  The enantiomers of the olive fly pheromone (1 and 4) were synthesized from ()-malic acid in amounts sufficient for the biological test.

  橄榄蝇信息素的对映体（1和4）是由（）-苹果酸合成的，其含量足以进行生物学测试。
• Studies on the α-acetylation of δ-valerolactone and ε-caprolactone
  作者：Jens Christoffers、Heiko Oertling、Peter Fischer、Wolfgang Frey

  DOI：10.1016/s0040-4020(03)00511-8

  日期：2003.5

  The synthetic approach to alpha-acetylated delta-valero- (7a) and epsilon-caprolactone (7b) is reported. While 7a was isolated in 21% yield from the respective iodoester 5a by an alkylation sequence involving transesterification and Finkelstein reaction, 7b was not obtained from 5b but the dimer 8. Also transesterification and olefin ring closing metathesis (RCM) failed to prepare 7b. RCM resulted in the dimeric lactone 10, showing that the formation of 14-membered rings is favored over that of seven-membered rings. A Mukaiyama-type Claisen reaction finally gave alpha-acetyl lactones 7a and 7b in practically useful quantity of about 10 g (62% yield): starting lactones 13a,b were converted to silylenolethers 14a,b, which were acetylated with acetic anhydride in presence of the Lewis acid catalyst TiCl4. However, acetylation depends on the addition sequence of starting materials: if the mixture of Ac2O/TiCl4 is added to 14b, lactone 7b can be further converted to give bis-oxepanonyl ethanols 15a,b. Both compounds 15 were characterized by X-ray crystallography and NMR. (C) 2003 Elsevier Science Ltd. All rights reserved.