1,1-Difluorooctan-2-ol | 153801-11-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 1,1-Difluorooctan-2-ol
• CAS: 153801-11-7
• 化学式: C₈H₁₆F₂O
• 分子量: 166.211
• InChiKey: VCEJTSPGGYAMFU-UHFFFAOYSA-N

物化性质

• 沸点：
  206.6±25.0 °C(Predicted)
• 密度：
  0.979±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-Difluorooctan-2-ol 、 乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 Acetic acid 1-difluoromethyl-heptyl ester
  参考文献：
  名称：

  A microbially-based approach for the synthesis of chiral secondary alcohols bearing the difluoromethyl or chlorodifluoromethyl group

  摘要：

  A synthetic approach to both enantiomers of the secondary alcohols [Ph(CH2)n CH(OH)CXF2 (n = 0-2) C6H13(CH2)n CH(OH)CFX2 (n = 0 or 2) and CXF2CH(OH)CH2CO2Et [X = H or Cl], involving the stereoselective hydrolysis of ester derivatives, is described. The absolute configurations of these difluoromethylated or chlorodifluoromethylated molecules were determined.

  DOI：

  10.1016/s0022-1139(00)81174-4
• 作为产物：
  描述：

  1,1-二氟-2-辛酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以91%的产率得到1,1-Difluorooctan-2-ol
  参考文献：
  名称：

  A microbially-based approach for the synthesis of chiral secondary alcohols bearing the difluoromethyl or chlorodifluoromethyl group

  摘要：

  A synthetic approach to both enantiomers of the secondary alcohols [Ph(CH2)n CH(OH)CXF2 (n = 0-2) C6H13(CH2)n CH(OH)CFX2 (n = 0 or 2) and CXF2CH(OH)CH2CO2Et [X = H or Cl], involving the stereoselective hydrolysis of ester derivatives, is described. The absolute configurations of these difluoromethylated or chlorodifluoromethylated molecules were determined.

  DOI：

  10.1016/s0022-1139(00)81174-4

文献信息

• Convenient Synthesis of Difluoromethyl Alcohols from Both Enolizable and Non-Enolizable Carbonyl Compounds with Difluoromethyl Phenyl Sulfone
  作者：G. K. Surya Prakash、Jinbo Hu、Ying Wang、George A. Olah

  DOI：10.1002/ejoc.200500101

  日期：2005.6

  difluoromethylation of carbonyl compounds (both enolizable and non-enolizable aldehydes and ketones) has been achieved by using a nucleophilic (phenylsulfonyl)difluoromethylation-reductive desul-fonylation strategy. Difluoromethyl phenyl sulfone acts as a difluoromethyl anion ("CF2H-") equivalent. (C Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

  通过使用亲核（苯磺酰基）二氟甲基化-还原性脱磺酰化策略，已经实现了羰基化合物（可烯醇化和不可烯醇化的醛和酮）的通用和有效的亲核二氟甲基化。二氟甲基苯砜充当二氟甲基阴离子（“CF 2 H-”）等价物。(C Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)。
• Optical resolution for producing optically active alcohol
  申请人：The Nisshin Oil Mills, Ltd.

  公开号：EP0709465A2

  公开（公告）日：1996-05-01

  A process for producing an optically active alcohol comprising carrying out interesterification between a racemic alcohol and an ester selected from the group consisting of (a) a diester between a lower monohydric alcohol and a saturated dicarboxylic acid having 14 or more carbon atoms, (b) a triglyceride of a saturated fatty acid having 16 or more carbon atoms, and (c) a monoester between a lower monohydric alcohol and a saturated fatty acid having 18 or more carbon atoms in the presence of lipase, preferably heat-resistant lipase, and in the presence or absence of a solvent, preferably in the absence of a solvent, under a substantially water-free condition, separating an optically active alcohol rich in either one of R- and S-forms from the reaction mixture, and adding an optically inactive non-racemic alcohol to the residue of the previous step to carry out interesterification under the same conditions as in the previous reaction to separate the other enantiomer. According to the present invention a racemic alcohol can easily be resolved into each enantiomer with high purity in good yield.

  一种生产光学活性醇的工艺，包括在脂肪酶存在下，在外消旋醇和选自以下组别的酯 之间进行酯化反应：(a)低级一元醇与具有 14 个或更多碳原子的饱和二羧酸之间的二酯；(b)具有 16 个或更多碳原子的饱和脂肪酸的甘油三酯；(c)低级一元醇与具有 18 个或更多碳原子的饱和脂肪酸之间的单酯、在有或无溶剂（最好是无溶剂）的条件下，在基本上无水的条件下，从反应混合物中分离出富含 R 型和 S 型中任一型的光学活性醇，并将光学不活泼的非外消旋醇加入到上一步的残留物中，在与上一步反应相同的条件下进行酯交换反应，以分离出另一种对映体。 根据本发明，外消旋醇可以很容易地以高纯度和高产率分离成每种对映体。
• Preparation of and Fluoroalkylation with (Chlorodifluoromethyl)trimethylsilane, Difluorobis(trimethylsilyl)methane, and 1,1,2,2-Tetrafluoro-1,2-bis(trimethylsilyl)ethane
  作者：Andrei K. Yudin、G. K. Surya Prakash、Denis Deffieux、Michael Bradley、Robert Bau、George A. Olah

  DOI：10.1021/ja962990n

  日期：1997.2.1

  CF2BrCl reacts with aluminum/N-methylpyrrolidinone in the presence of chlorotrimethylsilane to give Me(3)SiCF(2)Cl in high yield. Similarly, CF2Br2 gives Me(3)SiCF(2)Br with bromotrimethylsilane. Chlorodifluoromethylation of aldehydes using Me(3)SiCF(2)Cl and a catalytic amount of TBAF in polar solvents occurs at room temperature, providing difluoromethylated alcohols in two steps. Electroreduction of Me(3)SiCF(2)Cl in the presence of chlorotrimethylsilane gives Me(3)SiCF(2)SiMe(3) (anion-derived product) and Me(3)SiCF(2)CF(2)SiMe(3) (radical-derived product). Using THF/HMPA strongly favors the former, whereas THF/TDA-1 (tris(3,6-dioxaheptyl)amine) the latter. Me(3)SiCF(2)-SiMe(3) difluoromethylates aldehydes acting as a difluoromethylene dianion (''CF22-'' equivalent), whereas Me(3)SiCF(2)-CF(2)SiMe(3) acts at room temperature as an in situ source for the perfluorovinyl anion (due to beta-elimination of fluorotrimethylsilane). However, at low temperature the elimination pathway is suppressed and tetrafluoroethylene dianion (''-CF2CF2-'' equivalent) behavior is observed, The structure of Me(3)SiCF(2)CF(2)SiMe(3) was analyzed by X-ray diffraction. All of the studied fluoroalkylating reagents are moisture- and air-stable and can be readily obtained from a single convenient precursor (CF2BrCl).
• US5696299A
  申请人：——

  公开号：US5696299A

  公开（公告）日：1997-12-09
• A microbially-based approach for the synthesis of chiral secondary alcohols bearing the difluoromethyl or chlorodifluoromethyl group
  作者：Tomoya Kitazume、Masatomo Asai、Takashi Tsukamoto、Takashi Yamazaki

  DOI：10.1016/s0022-1139(00)81174-4

  日期：1992.3

  A synthetic approach to both enantiomers of the secondary alcohols [Ph(CH2)n CH(OH)CXF2 (n = 0-2) C6H13(CH2)n CH(OH)CFX2 (n = 0 or 2) and CXF2CH(OH)CH2CO2Et [X = H or Cl], involving the stereoselective hydrolysis of ester derivatives, is described. The absolute configurations of these difluoromethylated or chlorodifluoromethylated molecules were determined.

表征谱图