Ethyl 2,2-Difluoro-12-hydroxydodecanoate | 134682-41-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl 2,2-Difluoro-12-hydroxydodecanoate
• CAS: 134682-41-0
• 化学式: C₁₄H₂₆F₂O₃
• 分子量: 280.355
• InChiKey: FKQBPVDPYWIEDR-UHFFFAOYSA-N

物化性质

• 沸点：
  335.2±27.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  9-十烯-1-醇 在 水 、 铜 、 nickel dichloride 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 Ethyl 2,2-Difluoro-12-hydroxydodecanoate
  参考文献：
  名称：

  A new approach to .alpha.,.alpha.-difluoro-functionalized esters

  摘要：

  The addition reaction of iododifluoroacetates to alkenes is initiated by copper powder (10-20 mol %) at 50-60-degrees-C. Both terminal and internal alkenes give good yields of adducts. The reaction is also applicable to alkenes containing a variety of functional groups, such as epoxy, hydroxy, ketone, ester, and phosphonate moieties. This reaction can be carried out either neat or in solvents such as hexane, benzene, acetonitrile, DMF, DMSO, and HMPA and is suppressed by p-dinitrobenzene and di-tert-butyl nitroxide. A single electron transfer initiated radical mechanism is proposed. In the presence of nickel dichloride hexahydrate, reduction of the adducts with zinc in moist THF provides the corresponding alpha,alpha-difluoro esters in good yields.

  DOI：

  10.1021/jo00017a026

文献信息

• METHOD FOR PRODUCING FLUORINATED COMPOUND
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：US20190071376A1

  公开（公告）日：2019-03-07

  This invention solves the problem of providing an efficient, new method for producing a fluoromethylene-containing compound. The problem can be solved by a method for producing a compound represented by formula (1) or a ring-closed or ring-opened derivative of the compound, wherein R 1 represents an organic group, R X represents hydrogen or fluorine, R 2a , R 2b , R 2c , and R 2d are the same or different, and each represents —Y—R 21 or —N(—R 22 ) 2 , or R 2b and R 2c may join together to form a bond, wherein Y represents a bond, oxygen, or sulfur, R 21 represents hydrogen or an organic group, and R 22 , in each occurrence, is the same or different and represents hydrogen or an organic group; the method comprising step A of reacting a compound represented by formula (2), wherein X represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3), wherein the symbols are as defined above, in the presence of a reducing agent under light irradiation.

  这项发明解决了提供一种用于生产含氟甲烯基化合物的高效新方法的问题。该问题可通过一种用于生产由化学式（1）表示的化合物或该化合物的环闭合或环开放衍生物的方法来解决，其中R1代表有机基团，RX代表氢或氟，R2a、R2b、R2c和R2d相同或不同，每个代表—Y—R21或—N(—R22)2，或者R2b和R2c可以结合形成键，其中Y代表键、氧或硫，R21代表氢或有机基团，每次出现的R22相同或不同，代表氢或有机基团；该方法包括以下步骤：A. 在光照射下，在存在还原剂的条件下，使化学式（2）表示的化合物与化学式（3）表示的化合物发生反应。
• Photoredox-Catalyzed Hydrodifluoroalkylation of Alkenes Using Difluorohaloalkyl Compounds and a Hantzsch Ester
  作者：Shuhei Sumino、Misae Uno、Takahide Fukuyama、Ilhyong Ryu、Makoto Matsuura、Akinori Yamamoto、Yosuke Kishikawa

  DOI：10.1021/acs.joc.7b00609

  日期：2017.5.19

  Photoredox-catalyzed hydrodifluoroalkylation of alkenes proceeded smoothly in the presence of a Hantzsch ester as a hydrogen source under visible light irradiation. The reaction was also applicable to the hydrodifluoroalkylation of alkynes, and a continuous photo flow reaction was also successful.
• A new approach to .alpha.,.alpha.-difluoro-functionalized esters
  作者：Zhen Yu Yang、Donald J. Burton

  DOI：10.1021/jo00017a026

  日期：1991.8

  The addition reaction of iododifluoroacetates to alkenes is initiated by copper powder (10-20 mol %) at 50-60-degrees-C. Both terminal and internal alkenes give good yields of adducts. The reaction is also applicable to alkenes containing a variety of functional groups, such as epoxy, hydroxy, ketone, ester, and phosphonate moieties. This reaction can be carried out either neat or in solvents such as hexane, benzene, acetonitrile, DMF, DMSO, and HMPA and is suppressed by p-dinitrobenzene and di-tert-butyl nitroxide. A single electron transfer initiated radical mechanism is proposed. In the presence of nickel dichloride hexahydrate, reduction of the adducts with zinc in moist THF provides the corresponding alpha,alpha-difluoro esters in good yields.