3-(4-Chlorophenyl)-3-hydroxy-2,2-dimethylpropanal | 88903-21-3

• 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: 3-(4-Chlorophenyl)-3-hydroxy-2,2-dimethylpropanal
• CAS: 88903-21-3
• 化学式: C₁₁H₁₃ClO₂
• 分子量: 212.676
• InChiKey: LLPTWXIZJSRCQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-Chlorophenyl)-3-hydroxy-2,2-dimethylpropanal 在 sodium tetrahydroborate 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1-(4-chlorophenyl)-2,2-dimethylpropane-1,3-diol 、 1-(4-chlorophenyl)-2,2-dimethylpropane-1,3-diol
  参考文献：
  名称：

  Biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol reactions

  摘要：

  A highly stereoselective direct aldol condensation of ketones to aromatic aldehydes was realized; the trichlorosilyl enolether generated in situ in the presence of tetrachlorosilane is activated by catalytic amounts of an enantiomerically pure biheteroaromatic phosphine oxide to react with aldehydes, coordinated as well as activated by the chiral cationic hypervalent silicon species. This Lewis acid-mediated Lewis base-catalyzed transformation allowed, starting from two carbonyl compounds, to directly synthesize beta-hydroxy ketones generally with high anti stereoselectivity and up to 93% ee for the anti isomer. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.009
• 作为产物：
  描述：

  2-溴-2-甲基丙醛 、 4-氯苯甲醛 在 氢化钾 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到3-(4-Chlorophenyl)-3-hydroxy-2,2-dimethylpropanal
  参考文献：
  名称：

  醛烯醇化物。通过 TIN(II) 烯醇酸酯的交叉醛醇反应

  摘要：

  烯醇锡 (II) 是通过将金属锡氧化加成到 2-溴-2-甲基丙醛中而原位形成的，与醛反应以相当好的产率得到 β-羟基醛。

  DOI：

  10.1246/cl.1983.1727

文献信息

• Organocatalysts and Methods of Use in Chemical Synthesis
  申请人：Wang Wie

  公开号：US20070244328A1

  公开（公告）日：2007-10-18

  The present invention pertains generally to compositions comprising organocatalysts that facilitate stereo-selective reactions and the method of their synthesis and use. Particularly, the invention relates to metal-free organocatalysts for facilitation of stereo-selective reactions, and the method of their synthesis and use. These compounds have the structure of the Formulas (I) and (II). Where X is independently selected from CH 2 , N—R a , O, S or C═O; Y is CH 2 , N—R a , O, S or C═O, with the proviso that at least one of X or Y is CH 2 , and preferably both of X and Y are CH 2 ; R a is H, an optionally substituted C 1 -C 12 alkyl, preferably an optionally substituted C 1 -C 6 alkyl including a C 3 -C 6 cyclic alkyl group, or an optionally substituted aryl group, preferably an optionally substituted phenyl group; R b is H, an optionally substituted C 1 -C 12 alkyl, preferably an optionally substituted C 1 -C 6 acyclic or a a C 3 -C 6 cyclic alkyl group, CIIO, N(Me)O, CO(S)R a or the group of Formula (III). Where R c and R d are each independently H, F, Cl, an optionally substituted C 1 -C 20 alkyl, preferably an optionally substituted C 1 -C 12 alkyl, more preferably a C 1 -C 6 alkyl, and an optionally substituted aryl group, or together R c and R d form an optionally substituted carbocyclic or optionally substituted heterocyclic ring; R 1 is OH, OR, NR′R″, NHC(═O)R, NHSO 2 R; R 2 is H, F, Cl, an optionally substituted C 1 -C 20 alkyl, preferably an optionally substituted C 1 C 6 alkyl, an optionally substituted aryl group or a ═O group (which establishes a carbonyl group with the carbon to which ═O is attached; R 3 is H, OH, F, Cl, Br, I, Cl, an optionally substituted C 1 -C 20 alkyl, alkenyl or alkynyl (“hydrocarbyl”) group, preferably an optionally substituted C 1 -C 6 alkyl, or an optionally substituted aryl, such that the carbon to which R 3 is attached has an R or S configuration; R is II, an optionally substituted C 1 -C 20 alkyl, preferably an optionally substituted C 1 -C 6 alkyl, or an optionally substituted aryl group, R′ and R″ are each independently H, an optionally substituted C 1 -C 20 alkyl group, preferably an optionally substituted C 1 -C 6 alkyl, or an optionally substituted aryl group; or together R′ and R″ form an optionally substituted heterocyclic, preferably a 4 to 7 membered optionally substituted heterocyclic group or an optionally substituted heteroaryl ring with the nitrogen to which R′ and R″ are attached; and wherein said compound is free from a metal catalyst.

  本发明涉及一种包含有机催化剂的组合物，该组合物促进立体选择性反应及其合成和使用的方法。特别地，本发明涉及无金属有机催化剂，以促进立体选择性反应，以及其合成和使用的方法。这些化合物具有公式（I）和（II）的结构。其中，X独立地选自CH2、N—Ra、O、S或C═O；Y为CH2、N—Ra、O、S或C═O，但至少X或Y中的一个为CH2，最好是X和Y都为CH2；Ra为H、可选取代的C1-C12烷基，最好是可选取代的C1-C6烷基，包括C3-C6环烷基，或可选取代的芳基，最好是可选取代的苯基；Rb为H、可选取代的C1-C12烷基，最好是可选取代的C1-C6非环烷基或C3-C6环烷基，CIIO、N(Me)O、CO(S)Ra或公式（III）的基团。其中，Rc和Rd各自独立地为H、F、Cl、可选取代的C1-C20烷基，最好是可选取代的C1-C12烷基，更好是C1-C6烷基，以及可选取代的芳基，或者Rc和Rd一起形成可选取代的碳环或可选取代的杂环；R1为OH、OR、NR′R″、NHC(═O)R、NHSO2R；R2为H、F、Cl、可选取代的C1-C20烷基，最好是可选取代的C1-C6烷基、可选取代的芳基或═O基团（与═O相连的碳原子上形成羰基基团）；R3为H、OH、F、Cl、Br、I、Cl、可选取代的C1-C20烷基、烯基或炔基（“烃基”）团，最好是可选取代的C1-C6烷基，或可选取代的芳基，使得R3连接的碳原子具有R或S构型；R为II、可选取代的C1-C20烷基，最好是可选取代的C1-C6烷基，或可选取代的芳基团，R′和R″各自独立地为H、可选取代的C1-C20烷基团，最好是可选取代的C1-C6烷基，或可选取代的芳基团；或者R′和R″一起形成可选取代的杂环，最好是4到7个成员的可选取代的杂环基团或与R′和R″连接的氮原子一起形成可选取代的杂环芳基环；其中所述化合物不含金属催化剂。
• KATO, JUN-ICHI;MUKAIYAMA, TERUAKI, CHEM. LETT., 1983, N 11, 1727-1728
  作者：KATO, JUN-ICHI、MUKAIYAMA, TERUAKI

  DOI：——

  日期：——
• US7968734B2
  申请人：——

  公开号：US7968734B2

  公开（公告）日：2011-06-28
• ALDEHYDE ENOLATE. CROSS ALDOL REACTION via TIN(II) ENOLATE
  作者：Jun-ichi Kato、Teruaki Mukaiyama

  DOI：10.1246/cl.1983.1727

  日期：1983.11.5

  Tin(II) enolate, formed in situ by the oxidative addition of metallic tin to 2-bromo-2-methylpropanal, reacts with aldehydes to give β-hydroxy aldehydes in fairly good yields.

  烯醇锡 (II) 是通过将金属锡氧化加成到 2-溴-2-甲基丙醛中而原位形成的，与醛反应以相当好的产率得到 β-羟基醛。
• Biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol reactions
  作者：Sergio Rossi、Maurizio Benaglia、Andrea Genoni、Tiziana Benincori、Giuseppe Celentano

  DOI：10.1016/j.tet.2010.11.009

  日期：2011.1

  A highly stereoselective direct aldol condensation of ketones to aromatic aldehydes was realized; the trichlorosilyl enolether generated in situ in the presence of tetrachlorosilane is activated by catalytic amounts of an enantiomerically pure biheteroaromatic phosphine oxide to react with aldehydes, coordinated as well as activated by the chiral cationic hypervalent silicon species. This Lewis acid-mediated Lewis base-catalyzed transformation allowed, starting from two carbonyl compounds, to directly synthesize beta-hydroxy ketones generally with high anti stereoselectivity and up to 93% ee for the anti isomer. (C) 2010 Elsevier Ltd. All rights reserved.