ethyl 2,2-difluorohexadecanoate | 140420-95-7

• 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-difluorohexadecanoate
• CAS: 140420-95-7
• 化学式: C₁₈H₃₄F₂O₂
• 分子量: 320.464
• InChiKey: LGSHKBRENGBGES-UHFFFAOYSA-N

物化性质

• 沸点：
  357.0±27.0 °C(Predicted)
• 密度：
  0.942±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2,2-difluorohexadecanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以69%的产率得到2,2-difluoro-hexadecanoic acid
  参考文献：
  名称：

  二氟棕榈酸是埃及粘虫斜纹夜蛾（Spodoptera littoralis）的性信息素生物合成的潜在抑制剂。

  摘要：

  已经合成并充分表征了2，2-，3，3-和4，4-二氟棕榈酸（1-3）。通过氟化相应的二硫缩醛保护的酮酸酯，然后进行酶促皂化，可以制备酸2和3。在体内评估了酸1-3作为生物合成（Z，E）-9,11-十四碳二烯基乙酸酯的β-氧化步骤的抑制剂的作用，该乙酸酯是埃及夜蛾夜蛾斜纹夜蛾性信息素的主要成分。仅发现2,2-和3,3-衍生物，即那些在链缩短步骤中所涉及的位置含有两个氟原子的衍生物是活泼的，其活度类似于或低于相应的单氟酸。

  DOI：

  10.1016/0968-0896(96)00027-2
• 作为产物：
  描述：

  ethyl 2,2-difluoro-4-iodohexadecanoate 在 nickel (II) chloride hexahydrate 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以82%的产率得到ethyl 2,2-difluorohexadecanoate
  参考文献：
  名称：

  方便的AIBN引发的碘代二氟乙酸乙酯向烯烃的自由基加成反应

  摘要：

  描述了由AIBN引发的4-碘-2，2-二氟乙酸乙酯向各种烯烃底物中的加成。该加成通常导致相应的加成产物以良好的至优异的产率，并且在反应条件下可以容许各种官能团。

  DOI：

  10.1016/j.jfluchem.2008.03.002

文献信息

• A novel and practical method for the preparation of α,α-difluoro functionalized esters
  作者：Zhen-Yu Yang、Donald J. Burton

  DOI：10.1039/c39920000233

  日期：——

  α,α-Difluoro functionalized esters can be readily prepared in good yields from the reaction of iododifluoroacetates with alkenes and zinc in the presence of catalytic amounts of nickel dichloride hexahydrate.

  α,α-二氟官能化酯可以通过在二氯化镍六水合物催化量的存在下，由碘二氟乙酸酯与烯烃和锌反应，以良好的收率制备得到。
• Arenethiolate as a Dual Function Catalyst for Photocatalytic Defluoroalkylation and Hydrodefluorination of Trifluoromethyls
  作者：Can Liu、Kang Li、Rui Shang

  DOI：10.1021/acscatal.2c00592

  日期：2022.4.1

  a photocatalyst in photoredox catalysis, but we report herein that an arene thiolate with an appropriate substituent can be photoactivated under visible light to function as both a strongly reducing electron-donating redox catalyst and a HAT catalyst to enable catalytic C–F activation of trifluoromethyl substrates for selective hydrodefluorination and coupling with various alkenes in the presence of

  已知硫醇在光氧化还原催化中充当与光催化剂协同作用的氢原子转移催化剂，但我们在本文中报道了具有适当取代基的芳烃硫醇盐可以在可见光下光活化，从而起到强还原性给电子氧化还原的作用催化剂和 HAT 催化剂能够催化 C-F 活化三氟甲基底物，用于选择性加氢脱氟并在甲酸盐存在下与各种烯烃偶联。这些反应证明了硫醇盐作为双功能光催化剂的前景广阔。该方法的合成效用通过适用的三氟甲基底物的广泛范围来证明，包括三氟甲基化（杂）芳烃、三氟乙酸盐和三氟乙酰胺，它们表现出高水平的化学选择性。
• Spicamycin derivatives and their use as anticancer agents
  申请人：Kirin Beer Kabushiki Kaisha

  公开号：US05461036A1

  公开（公告）日：1995-10-24

  Spicamycin derivative represented by the formula (I) or a salt thereof: ##STR1## wherein R represents specific diverse substituents, for example, a linear alkadienyl having from 11 to 13 carbon atoms, and R.sub.1 and R.sub.2 respectively represent H or OH. Examples of specific compounds are 6-[4'-N-(N'-trans,trans 2,4-tridecadienoylglycyl)spicaminyl-amino]purine, and 6-[4'-N-(N'-trans,trans-2,4 dodecadienyoly glycyl) spicaminyl-amino]purine. Comopunds according to this invention are useful as a pharmaceutical for inhibition of a tumor, for example, human colon cancer.

  公式（I）代表的Spicamycin衍生物或其盐：其中R代表特定的不同取代基，例如，具有11至13个碳原子的直链烯基，而R.sub.1和R.sub.2分别代表H或OH。具体化合物的示例是6-[4'-N-(N'-反式、反式2,4-十三碳二烯酰基甘氨酸)孢菌素基氨基]嘌呤，以及6-[4'-N-(N'-反式、反式-2,4-十二碳烯基甘氨酸)孢菌素基氨基]嘌呤。根据本发明的化合物可用作抑制肿瘤的药物，例如，人类结肠癌。
• Nickel-catalyzed reaction of iododifluoroacetates with alkenes and zinc: a novel and practical route to .alpha.,.alpha.-difluoro-functionalized esters and .alpha.,.alpha.,.omega.,.omega.-tetrafluoro diesters
  作者：Zhen Yu Yang、Donald J. Burton

  DOI：10.1021/jo00045a027

  日期：1992.9

  lododifluoroacetates 1a-c react with alkenes and zinc in the presence of nickel dichloride hexahydrate in THF at room temperature or 60-degrees-C to give the corresponding alpha,alpha-difluoro esters in good yields. The reaction is also applicable to alkenes containing a variety of functional groups such as trimethylsilyl, hydroxy, ketone, and ester moieties. The reaction of 1 works well with dienes; the products formed depend on the length of chain of the dienes. 1,8-Nonadiene and 1,5-hexadiene afford the alpha,alpha,omega,omega-tetrafluoro diesters, while 1,6-heptadiene gave a mixture of ethyl 2,2-difluoro-8-nonenoate (19) and the cyclopentyl-substituted alpha,alpha-difluoro ester 20. When diallyl ether was used as a substrate, only the tetrahydrofuran derivative 21 was formed. The nickel-catalyzed reaction can be suppressed by p-dinitrobenzene and hydroquinone. A single electron transfer initiated radical mechanism is proposed.
• New fluorinated derivatives as esterase inhibitors. Synthesis, hydration and crossed specificity studies
  作者：Carmen Quero、Gloria Rosell、Oscar Jiménez、Sergio Rodriguez、M.Pilar Bosch、Angel Guerrero

  DOI：10.1016/s0968-0896(02)00467-4

  日期：2003.3

  A variety of new fluorinated chemicals have been prepared for the first time and tested as inhibitors of esterases, one of the main enzymes involved in pheromone catabolism, in two economically important pests, the Egyptian armyworm Spodoptera littoralis (SL) and the Mediterranean corn borer Sesamia nonagrioides (SN). Using the respective major component of the pheromone as substrate, the K-m and V-max of the antennal esterase of both insects resulted to be 5.66 x 10(-4) M and 8.47 x 10(-6) Mmin(-1) for SL and 1.61 x 10(-7) M and 1.25 x 10(-7) Mmin(-1) for SN, pointing out that SN esterase has a higher affinity for its corresponding substrate than SL. In general, the trifluoromethyl ketones (TFMKs) exhibited higher inhibitory potency than the corresponding difluoromethyl ketones (DFMKs) or difluoroaldehydes (DFAs). The compounds appeared to hydrate differently in aqueous solution, the extent of hydration following the order: alpha,alpha-DFMKs