1-isopropyl-3-butenyl acetate | 99893-48-8

• 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: 1-isopropyl-3-butenyl acetate
• 英文别名: 2-methylhex-5-en-3-yl acetate；acetic acid-(1-isopropyl-but-3-enyl ester)；Essigsaeure-(1-isopropyl-but-3-enylester)
• CAS: 99893-48-8
• 化学式: C₉H₁₆O₂
• mdl: MFCD07780434
• 分子量: 156.225
• InChiKey: DAIUAMYNKMDGLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-isopropyl-3-butenyl acetate 在 RuCl₃*3H₂O immobilized onto layered double hydroxide 盐酸 、 sodium hydroxide 、 sodium periodate 、 双氧水 、 对苯二酚 、 环氧氯丙烷 作用下， 以 甲醇 、 乙醚 、 水 、 乙腈 、 苯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis of Highly Functionalized δ-Lactone-Fused Cyclopentanoids

  摘要：

  报告了一种简短而高效的路线，可以从容易获得的同烯丙醇醋酸酯与1,2,3,4-四氯-5,5-二甲氧基环戊烯-1,3-二烯之间的Diels-Alder加合物出发，合成δ-内酯融合的环戊烷族化合物。由于同烯丙醇是通过烯丙金属的加成反应从相应的醛RCHO（R = 烷基、芳基）中衍生而来，因此该方法在R基团的选择上具有广泛的适用性。最初形成的1:1的抗异构体混合物经过钌催化氧化后，进而通过酸介导的醋酸基水解获得半醚6a-e。碱性过氧化氢对半醚的裂解，在与氮甲烷酯化后，得到了可通过色谱分离的抗异构体混合物7和8，整体产率高达54-68%。

  DOI：

  10.1055/s-2007-965948
• 作为产物：
  描述：

  2-甲基-5-己烯-3-醇 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以329 mg的产率得到1-isopropyl-3-butenyl acetate
  参考文献：
  名称：

  通过β-乙酰氧基消除对具有乙酰氧基的烯烃进行远程芳基取代

  摘要：

  芳基硼酸与具有远距离乙酰氧基的烯烃通过非离解链行走和β-乙酰氧基消除反应，实现了钯催化的远程芳基化取代。

  DOI：

  10.1002/anie.202111396

文献信息

• Copper-Catalyzed Oxy-Alkenylation of Homoallylic Alcohols to Generate Functional<i>syn</i>-1,3-Diol Derivatives
  作者：Dean Holt、Matthew J. Gaunt

  DOI：10.1002/anie.201501995

  日期：2015.6.26

  functionalized 1,3‐diol derivatives is reported. Employing a copper‐catalyzed oxy‐alkenylation strategy, a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts combine to form syn‐1,3‐carbonates in excellent yield and with high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide‐like

  报道了一种新型的合成多种功能化的1,3-二醇衍生物的方法。采用铜催化的氧-烯基化策略，一系列易于获得的取代的均烯丙基醇衍生物和烯基（芳基）碘鎓盐以优异的收率和高选择性结合形成顺式1,3-碳酸酯。此外，所形成的产物适合重复的反应序列，从而提供了高度复杂的聚酮化合物样片段。
• Study on the coupling of acyclic esters with alkenes – the synthesis of 2-(2-hydroxyalkyl)cyclopropanols via cascade cyclization using allylsamarium bromide
  作者：Yawei Tu、Liejin Zhou、Ruifeng Yin、Xin Lv、Robert A. Flowers II、Kimberly A. Choquette、Huili Liu、Qingsheng Niu、Xiaoxia Wang

  DOI：10.1039/c2cc34630c

  日期：——

  The radical cyclization between aliphatic acyclic esters and alkenes was achieved unprecedentedly in the presence of allylsamarium bromide with HMPA and H2O as additives. The cascade radical cyclization–ring-opening–anionic cyclization allowed facile and efficient access to 2-(2-hydroxyalkyl)cyclopropanols from readily available materials.

  在以 HMPA 和 H2O 为添加剂的烯丙基溴化铵存在下，前所未有地实现了脂肪族无环酯与烯烃之间的自由基环化。这种级联自由基环化-环-开环-阴离子环化的方法可以方便有效地从现有材料中获得 2-（2-羟基烷基）环丙醇。
• Preparation and reactivity of highly functionalized organometallics at the .alpha. position of oxygen or nitrogen
  作者：Paul Knochel、Tso Sheng Chou、Carole Jubert、Duddu Rajagopal

  DOI：10.1021/jo00055a010

  日期：1993.1

  Alpha-Halogenoalkyl carboxylates (FG-R1CH(X)(OCOR2); FG = COOR, CN, SR; X = I, Br) were readily prepared by the addition of an acid chloride or bromide (R2COX; X = Br or Cl) to an aldehyde (FG-RCHO) in the presence of a catalytic amount of ZnCl2. They insert efficiently zinc dust in THF-DMSO (X = Br, 8-10-degrees-C, 6-10 h) affording the corresponding zinc organometallics at the a position to oxygen FG-RCH(ZnBr)(OAc). After the addition of the THF-soluble copper salt CuCN.2LiCl, the corresponding copper reagents FG-RCH(Cu(CN)ZnBr)(OAc) are formed and reacted with various classes of electrophiles such as acid chlorides, aldehydes, enones, allylic and alkynyl halides, activated alkynes, nitro olefins and alkylidenemalonates providing polyfunctional molecules in excellent yields. Similarly, zinc organometallics at the a position to the nitrogen of cyclic imides were prepared by the zinc insertion to cyclic alpha-chloromethyl (or alpha-chloroethyl) imides. After their transmetalation to the corresponding copper organometallic ((R1CO)2NCH(R)(Cu(CN)ZnCl); R = Me or H), they were reacted with allylic and alkynyl halides and ethyl propiolate affording polyfunctional imides. The reaction of cyclic N-(chloromethyl)imides with aldehydes in the presence of chromium(II) chloride in THF furnishes protected amino alcohols in 36-95% yield.
• Allylstannation
  作者：Andrea Boaretto、Daniele Marton、Giuseppe Tagliavini

  DOI：10.1016/0022-328x(85)80121-2

  日期：1985.6
• BOARETTO, A.;MARTON, D.;TAGLIAVINI, G., J. ORGANOMET. CHEM., 1985, 288, N 3, 283-287
  作者：BOARETTO, A.、MARTON, D.、TAGLIAVINI, G.

  DOI：——

  日期：——