2-(2,2-difluoro-1-phenylcyclopropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1010689-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2,2-difluoro-1-phenylcyclopropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1010689-64-1
• 化学式: C₁₅H₁₉BF₂O₂
• 分子量: 280.122
• InChiKey: KMFYVPWNSHRSNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  2-(2,2-difluoro-1-phenylcyclopropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 、 3-氯丙烯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 乙基苯 、 正戊烷 为溶剂， 以60%的产率得到2-[1-(2,2-difluoro-1-phenylcyclopropyl)allyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Boron-Substituted Difluorocyclopropanes:  New Building Blocks of gem-Difluorocyclopropanes

  摘要：

  Cycloaddition of difluorocarbene to alkenyl boronates 3 gave boron-substituted gem-difluorocyclopropanes 2 in stereospecific fashion. Upon treatment with lithium carbenoids, cyclopropyl boronates 2 underwent one-carbon homologation to afford a variety of gem-difluorocyclopropanes in good yields.

  DOI：

  10.1021/ol702851t
• 作为产物：
  描述：

  sodium chlorodifluoroacetate 、 1-苯基乙烯基硼酸频哪酯 以 四氢呋喃 为溶剂， 反应 0.08h， 以70%的产率得到2-(2,2-difluoro-1-phenylcyclopropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  An Improved Method for Difluorocyclopropanation of Alkenes

  摘要：

  Difluorocyclopropanation of alkenes using fluorinated acetate salts using convential heating is often a slow, inefficient, and energy-intensive process. We report here a modified protocol which enables the rapid (<5 min) preparation of 1,1-difluorocyclopropanes, using microwave irradiation. The new procedure is not only considerably faster than previously reported methods, but it also employs easily removed, low boiling-point solvents and avoids the use of highly toxic or ozone-depleting substances.

  DOI：

  10.1055/s-0033-1341155

文献信息

• METHOD FOR PRODUCING DIFLUOROCYCLOPROPANE COMPOUND
  申请人：Amii Hideki

  公开号：US20120277458A1

  公开（公告）日：2012-11-01

  Provided is a method for producing a difluorocyclopropane compound under milder reaction conditions and with high selectivity and high yield. The method for producing a difluorocyclopropane compound of the present invention is characterized by using sodium bromodifluoroacetate as a difluorocyclopropanation agent. With the disclosed method, a difluorocyclopropane compound can be produced under milder reaction conditions and with a higher conversion rate and a higher yield compared to conventional art. Further, by-products can be reduced significantly, thus allowing waste to be greatly reduced. Accordingly, the production method of the present invention is easy to implement industrially (can be employed on an industrial scale) and is thus extremely practical and useful.

  提供了一种在较温和的反应条件下、具有高选择性和高产率的制备二氟环丙烷化合物的方法。本发明的制备二氟环丙烷化合物的方法的特点是使用溴二氟乙酸钠作为二氟环丙烷化试剂。通过所披露的方法，与传统技术相比，可以在较温和的反应条件下生产二氟环丙烷化合物，并且具有更高的转化率和更高的产率。此外，副产物可以显著减少，从而大大减少废物。因此，本发明的生产方法易于在工业上实施（可在工业规模上应用），因此极其实用和有用。
• Sodium Bromodifluoroacetate: A Difluorocarbene Source for the Synthesis of gem-Difluorocyclopropanes
  作者：Hideki Amii、Kojun Oshiro、Yoshimichi Morimoto

  DOI：10.1055/s-0029-1218754

  日期：2010.6

  As a new difluorocarbene source, sodium bromodifluoroacetate (BrCF2CO2Na) was found to be effective for high-yielding­ synthesis of gem-difluorocyclopropanes and gem-difluorocyclopropenes under mild conditions. fluorine - carbenes - cycloaddition - cyclopropanes - cyclopropenes­

  发现溴二氟乙酸钠（BrCF 2 CO 2 Na）作为一种新的二氟卡宾来源，可在温和条件下有效地高产合成宝石-二氟环丙烷和宝石-二氟环丙烯。 氟-卡宾-环加成-环丙烷-环丙烯
• <i>gem</i> -Difluorocyclopropanation of Alkenyl Trifluoroborates with the CF₃ SiMe₃ -NaI System
  作者：Oleksandr V. Hryshchuk、Anatolii O. Varenyk、Yevhen Yurov、Yuliya O. Kuchkovska、Andriy V. Tymtsunik、Oleksandr O. Grygorenko

  DOI：10.1002/ejoc.202000346

  日期：2020.4.23

  Difluorocyclopropanation of alkenyl trifluoroborates using the TMSCF3–NaI system was achieved in up to 90 % yield on a multigram scale. The developed method allowed preparation of monocyclic, spiro‐ and fused‐bicyclic gem‐difluorocyclopropanes bearing additional functional groups.

  使用TMSCF 3 –NaI系统对三氟硼酸烯基酯进行二氟环丙烷化反应，其克数可达90％。所开发的方法允许制备带有额外官能团的单环，螺环和稠合双环宝石-二氟环丙烷。
• 一种二氟三元环化合物的制备方法
  申请人：上海麦克林生化科技有限公司

  公开号：CN113956159A

  公开（公告）日：2022-01-21

  本发明公开了一种二氟三元环化合物的合成方法,以烯烃类化合物和过量的氟磺酰基二氟乙酸甲酯为原料，以甲苯、THF或二氧杂环乙烷为溶剂，加入碘化钠和三甲基氯硅烷，在惰性气体保护下制备而成。本发明二氟三元环化合物的合成方法更方便，且该反应的投料操作简便，适用范围更广，反应条件温和，更适合工艺放大。
• An Improved Method for Difluorocyclopropanation of Alkenes
  作者：Joseph Sweeney、Duncan Gill、Neil McLay、Michael Waring、Christopher Wilkinson

  DOI：10.1055/s-0033-1341155

  日期：——

  Difluorocyclopropanation of alkenes using fluorinated acetate salts using convential heating is often a slow, inefficient, and energy-intensive process. We report here a modified protocol which enables the rapid (<5 min) preparation of 1,1-difluorocyclopropanes, using microwave irradiation. The new procedure is not only considerably faster than previously reported methods, but it also employs easily removed, low boiling-point solvents and avoids the use of highly toxic or ozone-depleting substances.