| 1391849-26-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1391849-26-5
• 化学式: C₁₂H₇F₃O₂
• 分子量: 240.182
• InChiKey: DMJKVIMGPYZSAA-UHFFFAOYSA-N

物化性质

• 沸点：
  374.4±42.0 °C(Predicted)
• 密度：
  1.484±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  、 丙炔酸乙酯 在 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以60%的产率得到
  参考文献：
  名称：

  Phosphine-Catalyzed Dual Umpolung Domino Michael Reaction: Facile Synthesis of Hydroindole- and Hydrobenzofuran-2-Carboxylates

  摘要：

  A highly atom-economical, chemoselective, and stereoselective Lewis base (LB)-catalyzed dual umpolung domino Michael reaction between cyclohexadienones and alkynyl esters has been developed. PPh3, as a LB catalyst, afforded either the hydroindole-2-carboxylates or hydrobenzofuran-2-carboxylates 3 as a single diastereomer in high yields (up to 89%). An obtained product could be easily transformed to a (S*,S*,R*)-octahydroindole-2-carboxylic acid ((S*,S*,R*)-Oic) analogue.

  DOI：

  10.1021/acscatal.8b01011

文献信息

• Phosphine‐Catalyzed β,γ‐Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center
  作者：Shinobu Takizawa、Kenta Kishi、Yasushi Yoshida、Steffen Mader、Fernando Arteaga Arteaga、Shoukou Lee、Manabu Hoshino、Magnus Rueping、Makoto Fujita、Hiroaki Sasai

  DOI：10.1002/anie.201508022

  日期：2015.12.14

  enantio‐, diastereo‐, regio‐, and chemoselective phosphine‐catalyzed β,γ‐umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence, involving oxy‐Michael and Rauhut–Currier reactions, produced highly functionalized tetrahydrobenzofuranones, bearing a chiral tetrasubstituted stereogenic center, in up to 96 % ee.

  首次开发了烯丙基酯与二烯酮的对映体，非对映体，区域和化学选择性膦催化的β，γ-粗蛋白多米诺骨反应。设计的顺序涉及oxy-Michael和Rauhut-Currier反应，产生了高度官能化的四氢苯并呋喃酮，带有手性四取代的立体异构中心，ee高达96％。
• Enantioselective Synthesis of α-Alkylidene-γ-Butyrolactones: Intramolecular Rauhut-Currier Reaction Promoted by Acid/Base Organocatalysts
  作者：Shinobu Takizawa、Tue Minh-Nhat Nguyen、André Grossmann、Dieter Enders、Hiroaki Sasai

  DOI：10.1002/anie.201201542

  日期：2012.5.29

  Teaming up: The title reaction has been developed to deliver the product α‐alkylidene‐γ‐butyrolactones as single diastereomers with up to 98 % ee (see scheme; Ts=4‐toluenesulfonyl). The enantioselective process is catalyzed by 1, which contains both Lewis base and Brønsted acid moieties.

  合作：已经开发了标题反应，可将产物α-亚烷基-γ-丁内酯作为单一非对映异构体提供，其ee最高可达98％  （参见方案； Ts = 4-甲苯磺酰基）。对映选择性过程由1催化，其中既包含路易斯碱又包括布朗斯台德酸部分。
• Facile synthesis of α-methylidene-γ-butyrolactones: intramolecular Rauhut–Currier reaction promoted by chiral acid–base organocatalysts
  作者：Shinobu Takizawa、Tue Minh-Nhat Nguyen、André Grossmann、Michitaka Suzuki、Dieter Enders、Hiroaki Sasai

  DOI：10.1016/j.tet.2012.11.046

  日期：2013.1

  The acid–base organocatalyzed intramolecular Rauhut–Currier (RC) reaction of the dienone enolates has been developed. The enantioselective RC process produces the highly functionalized α-methylidene-γ-butyrolactones as a single diastereomer with up to 98% ee.

  已开发出二烯酮烯酸酯的酸碱有机催化的分子内Rauhut-Currier（RC）反应。对映选择性RC工艺可生产高度官能化的α-亚甲基-γ-丁内酯，作为单一的非对映异构体，ee最高可达98％。