(1S,3R,4R,6S)-2,2,5,5-tetrafluoro-1,6-bis(hydroxymethyl)bicyclopropane | 244640-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4R,6S)-2,2,5,5-tetrafluoro-1,6-bis(hydroxymethyl)bicyclopropane
• 英文别名: [(1S,3R)-3-[(1R,3S)-2,2-difluoro-3-(hydroxymethyl)cyclopropyl]-2,2-difluorocyclopropyl]methanol
• CAS: 244640-66-2
• 化学式: C₈H₁₀F₄O₂
• 分子量: 214.16
• InChiKey: LUMYABWBGLCRQN-ZXXMMSQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(4-nonyloxyphenyl)benzoyl chloride 、 (1S,3R,4R,6S)-2,2,5,5-tetrafluoro-1,6-bis(hydroxymethyl)bicyclopropane 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以21%的产率得到1-[4-(4-nonyloxyphenyl)benzoyloxymethyl]-(1S,3R,4R,6S)-2,2,5,5-tetrafluorobicyclopropylmethyl 4-(4-nonyloxyphenyl)-benzoate
  参考文献：
  名称：

  Synthesis of Novel Liquid Crystals which Possessgem-Difluorocyclopropane Moieties

  摘要：

  我们合成了两种具有宝石-二氟环丙烷分子的新型手性液晶分子，并考察了它们的液晶特性。

  DOI：

  10.1246/cl.2003.494
• 作为产物：
  描述：

  Acetic acid 3'-acetoxymethyl-3,3,2',2'-tetrafluoro-bicyclopropyl-2-ylmethyl ester 在 lipase SL₂₅ 作用下， 反应 4.0h， 以30%的产率得到(1S,3R,4R,6S)-2,2,5,5-tetrafluoro-1,6-bis(hydroxymethyl)bicyclopropane
  参考文献：
  名称：

  Synthesis of Novel Liquid Crystals which Possessgem-Difluorocyclopropane Moieties

  摘要：

  我们合成了两种具有宝石-二氟环丙烷分子的新型手性液晶分子，并考察了它们的液晶特性。

  DOI：

  10.1246/cl.2003.494

文献信息

• gem-Difluorocyclopropane as core molecule candidate for liquid crystal compounds
  作者：Toshiyuki Itoh、Manabu Kanbara、Masakazu Ohashi、Shuichi Hayase、Motoi Kawatsura、Takashi Kato、Kazutoshi Miyazawa、Yumiko Takagi、Hidemitsu Uno

  DOI：10.1016/j.jfluchem.2007.05.004

  日期：2007.10

  The synthesis of a novel chiral gem-difluorocyclopropane building block has been accomplished using chemo-enzymatic reaction protocol; the prochiral diol of 1,4-bis(2,2-difluoro-3-(hydroxymethyl)cyclopropyl)benzene (5) was converted to the corresponding chiral diacetate by Pseudomonas lipase (lipase SL-25, Meito)-catalyzed transesterification with vinyl acetate as acyl donor with > 99% enantiomeric excess. Various types of diesters or dialkyl ether were prepared from the diol and their helical twisting power (HTP) was evaluated by addition of 1.0 wt% to a non-chiral nematic liquid crystal host; the HTP was significantly dependent on the structure of ester or ether moieties and diester of diol 5 with isopropylfumalic acid showed the largest HTP. (C) 2007 Elsevier B.V. All rights reserved.
• Synthesis of optically active bisdifluorocyclopropanes through a chemo-enzymatic reaction strategy
  作者：Koichi Mitsukura、Satoshi Korekiyo、Toshiyuki Itoh

  DOI：10.1016/s0040-4039(99)01088-6

  日期：1999.7

  The first synthesis of bisdifluorocyclopropane derivatives has been accomplished via a chemo-enzymatic reaction strategy; (E)- or (Z)-3-tributylstannyl-2-propenols were prepared and their conversion led to the (trans, trans)- and(cis, cis) -bisdifluorocyclopropanes. The subsequent lipase-catalyzed reaction efficiently afforded optically active (trans, trans)2,2,5,5-tetrafluoro-1,6-bis(hydroxymethyl)bicyclopropane. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.