(1S,2S)-(+)-trans-2-phenylcyclopentanecarboxaldehyde | 97276-81-8

• 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: (1S,2S)-(+)-trans-2-phenylcyclopentanecarboxaldehyde
• 英文别名: (1S,2S)-2-phenylcyclopentanecarbaldehyde；(1S,2S)-2-phenylcyclopentane-1-carbaldehyde
• CAS: 97276-81-8
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: RRDDMVLLDFPZDS-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2S)-(+)-trans-2-phenylcyclopentanecarboxaldehyde 在 dimethyl sulfide borane 作用下， 以95%的产率得到(1S,2S)-(+)-trans-(2-phenylcyclopentyl)methanol
  参考文献：
  名称：

  通过有机硼烷进行手性合成。3. 将基本 100% 光学纯度的硼酸酯转化为具有极高对映体纯度的醛、酸和同系醇

  摘要：

  L'homologation des烷基-2二氧硼烷-1,3,2 en α-甲氧基烷基-2dioxaborinannes-1,3,2 (I) est effectuee par traitement avec le [甲氧基苯硫基] 甲基锂 suivi d'un traitement avec HgCl 2 。Les compose I sont oxydes avec H 2 O 2 Pour donner les aldehydes 通讯员，avec une tres forte purete optique。Les aldehydes peuvent etre reduits et oxydes en utilisant各自 le borane-methylesulfure et l'acide chromique aqueux

  DOI：

  10.1021/ja00303a026
• 作为产物：
  描述：

  1-环戊烯甲醛 在 acetate buffer 、 4 Angstroems MS 、 (1R,2R)-1,2-dimethoxy-1,2-diphenylethane 作用下， 以 正己烷 为溶剂， 反应 18.5h， 生成 (1S,2S)-(+)-trans-2-phenylcyclopentanecarboxaldehyde
  参考文献：
  名称：

  Design, Synthesis, and Application of a C₂ Symmetric Chiral Ligand for Enantioselective Conjugate Addition of Organolithium to α,β-Unsaturated Aldimine

  摘要：

  A C-2 symmetric chiral diether ligand, (1R,2R)-1,2-dimethoxy-1,2-diphenylethane was designed and synthesized on the basis of the concept of an asymmetric oxygen atom. Mediated by the chiral diether, high enantioselectivities were achieved in conjugate addition of organolithiums to naphthaldehyde imine and cyclic and acyclic alpha,beta-unsaturated aldimines. The absolute configuration of the product is predictable by the model.

  DOI：

  10.1021/jo9813181

文献信息

• Stereoselective Synthesis of (2<i>E</i>,4<i>Z</i>)-Dienamides Employing (Triphenylphosphoranylidene)ketene
  作者：Steffen Pachali、Christine Hofmann、Georg Rapp、Rainer Schobert、Angelika Baro、Wolfgang Frey、Sabine Laschat

  DOI：10.1002/ejoc.200900176

  日期：2009.6

  reaction between ylide Ph3PCCO, amines and aldehydes is known to afford selectively (E)-α,β-unsaturated amides. We applied a variant of this methodology to the preparation of (2E,4Z)-dienamides 11 utilizing the phosphonium salt formation from ethyl 5-aminopentanoate hydrochloride and Ph3PCCO followed by deprotonation with DBU and a Wittig olefination of the corresponding ylide with various (Z)-α,β-unsaturated

  已知叶立德 Ph3PCCO、胺和醛之间的三组分反应可选择性地提供 (E)-α,β-不饱和酰胺。我们应用这种方法的变体来制备 (2E,4Z)-二烯酰胺 11，利用 5-氨基戊酸乙酯盐酸盐和 Ph3PCCO 形成的鏻盐，然后用 DBU 去质子化，并用各种 (Z) -α,β-不饱和醛 10. (2E,4Z)-二烯酰胺 11 的分离产率高达 80%。在反应过程中，起始醛 10 的 (Z)-构型保持不变。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Access to 5-bromopentanal and 6-bromohexanal derivatives <i>via</i> the bromination/hydrolysis of C,O-bis-zirconocenes generated from unsaturated Weinreb amides
  作者：Aurélien Coelho、Jean-Bernard Behr、Jean-Luc Vasse

  DOI：10.1039/d2ob01073a

  日期：——

  Access to 5-bromopentanal and 6-bromohexanal derivatives from Weinreb amides is described. The method relies on the sequential C-bromination/zircona-aminal hydrolysis of bis-C,O-zirconocenes, which are generated in situ from unsaturated Weinreb amides using Schwartz's reagent. Synthetic illustrations of such bromo-aldehydes, which can act as carbocycle and heterocycle precursors, are also presented

  描述了从 Weinreb 酰胺中获得 5-溴戊醛和 6-溴己醛衍生物的途径。该方法依赖于使用 Schwartz 试剂从不饱和 Weinreb 酰胺原位生成的双-C、O-锆茂的连续 C-溴化/氧化锆-氨基水解。还介绍了可以作为碳环和杂环前体的这种溴醛的合成说明。
• Novel strategy of using a C2 symmetric chiral diether in the enantioselective conjugate addition of an organolithium to an .alpha.,.beta.-unsaturated aldimine
  作者：Kiyoshi Tomioka、Mitsuru Shindo、Kenji Koga

  DOI：10.1021/ja00203a032

  日期：1989.10
• Regio- and diastereoselective SN2′ or SN2″ reactions on chiral acetals of cyclic aldehydes promoted by PhCu, BF3
  作者：Frédérique Mazé、Martin Purpura、Frédéric Bernaud、Pierre Mangeney、Alexandre Alexakis

  DOI：10.1016/s0957-4166(01)00319-6

  日期：2001.8

  The regio- and diastereoselectivity of the addition of PhCu, BF3 reagent on chiral acetals derived from several mono or dienic aldehydes was studied. It as found that monoethylenic acetals react regio- and diastercoselectively via Lin overall anti S(N)2' reaction. The regioselectivity observed with the dienic acetals seems to be strongly dependent on the nature of the acetal. In all cases the S(N)2'' reaction was the result of an anti process. (C) 2001 Elsevier Science Ltd. All rights reserved.
• TOMOIOKA, KIYOSHI;SHINDO, MITSURU;KOGA, KENJI, J. AMER. CHEM. SOC., 111,(1989) N1, C. 8266-8268
  作者：TOMOIOKA, KIYOSHI、SHINDO, MITSURU、KOGA, KENJI

  DOI：——

  日期：——