(2S)-2-fluoro-2-phenylpropanal | 862669-01-0

• 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: (2S)-2-fluoro-2-phenylpropanal
• 英文别名: 2-fluoro-2-phenylpropionaldehyde
• CAS: 862669-01-0
• 化学式: C₉H₉FO
• 分子量: 152.168
• InChiKey: JBUOWRXDFOIKSS-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-fluoro-2-phenylpropanal 在 sodium tetrahydroborate 作用下， 以 甲苯 为溶剂， 生成 (S)-(+)-2-fluoro-2-phenyl-1-propanol
  参考文献：
  名称：

  Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C–F bond cleavage

  摘要：

  高度对映选择性氟化α-支链醛利用新开发的手性初级胺催化剂实现。

  DOI：

  10.1039/c5sc03486h
• 作为产物：
  描述：

  2-苯基丙醛 在 3,5-二硝基苯甲酸 、 (11bR)-4-氨基-2,6-二(3,5-二叔丁基苯基)-4,5-二氢-3H-环庚并[1,2-a:7,6-a']联萘-4-甲酸乙酯 、 N-氟代双苯磺酰胺 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以95%的产率得到
  参考文献：
  名称：

  Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C–F bond cleavage

  摘要：

  高度对映选择性氟化α-支链醛利用新开发的手性初级胺催化剂实现。

  DOI：

  10.1039/c5sc03486h

文献信息

• Non-Biaryl Atropisomers in Organocatalysis
  作者：Sebastian Brandes、Barbara Niess、Marco Bella、Auxiliadora Prieto、Jacob Overgaard、Karl Anker Jørgensen

  DOI：10.1002/chem.200600495

  日期：2006.8.7

  ketone, in up to 93 % ee (ee=enantiomeric excess), as well as for the asymmetric Friedel-Crafts amination of a variety of 2-naphthols, permitting the preparation of the latter in up to 98 % ee. The aminated 8-amino-2-naphthol itself is the first chiral organocatalyst based on non-biaryl atropisomerism. The two enantiomers of this chiral primary amine can be used for the direct alpha-fluorination of alpha-branched

  可以通过简单的胺化步骤制备一种新的6'-羟基金鸡纳生物碱，该类生物碱在喹啉核心的5'位置具有非联芳基阻转异构功能。这些是金鸡纳生物碱经典核心中引入的阻转异构原理的第一批衍生物。胺化的金鸡纳生物碱是有效的有机催化剂，可将高达93％ee（ee =对映体过量）的β-酮酸酯迈克尔加成到丙烯醛和甲基乙烯基酮中，以及各种不对称的Friedel-Crafts胺化反应。 2-萘酚，允许制备高达98％ee的后者。胺化的8-氨基-2-萘酚本身是第一种基于非联芳基阻转异构的手性有机催化剂。该手性伯胺的两种对映异构体可用于α-支化醛的直接α-氟化。氟化化合物因此可以以高达90％ee的浓度进入。
• Asymmetric Fluorination of α-Branched Aldehydes by Chiral Primary Amine Catalysis: Reagent-Controlled Enantioselectivity Switch
  作者：Linfeng Cui、Yang’en You、Xueling Mi、Sanzhong Luo

  DOI：10.1021/acs.joc.8b00279

  日期：2018.4.6

  Asymmetric fluorination of α-branched aldehydes catalyzed by chiral primary amines under mild conditions has been developed. Both enantiomers could be obtained with good yields (up to 96%) and a high enantioselectivity (up to 90% ee) by a simple swap of the fluorination reagents.

  已经开发了在温和条件下手性伯胺催化的α-支链醛基的不对称氟化。两种对映异构体可以通过简单地交换氟化试剂而以良好的收率（高达96％）和高的对映选择性（高达90％ee）获得。
• Highly diastereoselective synthesis of enantioenriched <i>anti</i>-α-allyl-β-fluoroamines
  作者：Philip J. Chevis、Sirilak Wangngae、Thanaphat Thaima、Anthony W. Carroll、Anthony C. Willis、Mookda Pattarawarapan、Stephen G. Pyne

  DOI：10.1039/c9cc02765c

  日期：——

  A highly diastereoselective synthesis of anti-α-allyl-β-fluoroamines has been developed involving enantioselective α-fluorination of aldehydes followed by a diastereoselective Petasis allyl borono-Mannich reaction. The products are obtained generally in good overall yields for the two steps and with drs of 97 : 3–99 : 1 and ees of 86–92%. Selected products were converted to 3-, 5- and 6-membered ring

  已经开发了抗-α-烯丙基-β-氟胺的高度非对映选择性的合成，包括醛的对映选择性α-氟化，然后进行非对映选择性的Petasis烯丙基硼烷-曼尼希反应。通常，两步获得的产品收率均良好，drs为97：3–99：1，ee为86-92％。将选择的产物转化为3、5和6元环杂环，后两种结合有外环氟。
• A Simple Primary Amine Catalyst for Enantioselective α-Hydroxylations and α-Fluorinations of Branched Aldehydes
  作者：Michael R. Witten、Eric N. Jacobsen

  DOI：10.1021/acs.orglett.5b01193

  日期：2015.6.5

  A new primary amine catalyst for the asymmetric a-hydroxylation and a-fluorination of alpha-branched aldehydes is described. The products of the title transformations are generated in excellent yields with high enantioselectivities. Both processes can be performed within short reaction times and on gram scale. The similarity in results obtained in both reactions, combined with computational evidence, implies a common basis for stereoinduction and the possibility of a general catalytic mechanism for a-functionalizations. Promising initial results in alpha-amination and alpha-chlorination reactions support this hypothesis.
• Rapid, General Access to Chiral β-Fluoroamines and β,β-Difluoroamines via Organocatalysis
  作者：Olugbeminiyi O. Fadeyi、Craig W. Lindsley

  DOI：10.1021/ol802930q

  日期：2009.2.19

  A rapid, general route to enantiopure beta-fluoroamines and beta,beta-difluoroamines has been developed employing organocatalysis in both a two-pot and a one-pot procedure. Both chemical yields (64-82%) and enantioselectivity (94-98% ee) were excellent and represent a significant improvement in the art of preparing chemically diverse beta-fluoroamines from readily available precursors.